NCBI Taxonomy: 39169

Rosmarinic acid

C18H16O8 (360.0845)

Rosmarinic acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid. It is commonly found in species of the Boraginaceae and the subfamily Nepetoideae of the Lamiaceae. It is a red-orange powder that is slightly soluble in water, but well soluble is most organic solvents. Rosmarinic acid is one of the polyphenolic substances contained in culinary herbs such as perilla (Perilla frutescens L.), rosemary (Rosmarinus officinalis L.), sage (Salvia officinalis L.), mint (Mentha arvense L.), and basil (Ocimum basilicum L.). These herbs are commonly grown in the garden as kitchen herbs, and while used to add flavor in cooking, are also known to have several potent physiological effects (PMID: 12482446, 15120569). BioTransformer predicts that rosmarinic acid is a product of methylrosmarinic acid metabolism via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction occurring in humans and human gut microbiota and catalyzed by the liver carboxylesterase 1 (P23141) enzyme (PMID: 30612223). (R)-rosmarinic acid is a stereoisomer of rosmarinic acid having (R)-configuration. It has a role as a plant metabolite and a geroprotector. It is a conjugate acid of a (R)-rosmarinate. It is an enantiomer of a (S)-rosmarinic acid. Rosmarinic acid is a natural product found in Dimetia scandens, Scrophularia scorodonia, and other organisms with data available. See also: Rosemary Oil (part of); Comfrey Root (part of); Holy basil leaf (part of) ... View More ... D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D015842 - Serine Proteinase Inhibitors D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors Isolated from rosemary, mint, sage, thyme, lemon balm and other plants D002491 - Central Nervous System Agents > D000700 - Analgesics A stereoisomer of rosmarinic acid having (R)-configuration. D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents Acquisition and generation of the data is financially supported in part by CREST/JST. Rosmarinic acid is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively. Rosmarinic acid is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively.

Coumarin

C9H6O2 (146.0368)

Coumarin appears as colorless crystals, flakes or colorless to white powder with a pleasant fragrant vanilla odor and a bitter aromatic burning taste. (NTP, 1992) Coumarin is a chromenone having the keto group located at the 2-position. It has a role as a fluorescent dye, a plant metabolite and a human metabolite. Coumarin is a natural product found in Eupatorium cannabinum, Eupatorium japonicum, and other organisms with data available. Coumarin is o hydroxycinnamic acid. Pleasant smelling compound found in many plants and released on wilting. Has anticoagulant activity by competing with Vitamin K. Coumarin is a chemical compound/poison found in many plants, notably in high concentration in the tonka bean, woodruff, and bison grass. It has a sweet scent, readily recognised as the scent of newly-mown hay. It has clinical value as the precursor for several anticoagulants, notably warfarin. --Wikipedia. Coumarins, as a class, are comprised of numerous naturally occurring benzo-alpha-pyrone compounds with important and diverse physiological activities. The parent compound, coumarin, occurs naturally in many plants, natural spices, and foods such as tonka bean, cassia (bastard cinnamon or Chinese cinnamon), cinnamon, melilot (sweet clover), green tea, peppermint, celery, bilberry, lavender, honey (derived both from sweet clover and lavender), and carrots, as well as in beer, tobacco, wine, and other foodstuffs. Coumarin concentrations in these plants, spices, and foods range from <1 mg/kg in celery, 7000 mg/kg in cinnamon, and up to 87,000 mg/kg in cassia. An estimate of human exposure to coumarin from the diet has been calculated to be 0.02 mg/kg/day. Coumarin is used as an additive in perfumes and fragranced consumer products at concentrations ranging from <0.5\\\\% to 6.4\\\\% in fine fragrances to <0.01\\\\% in detergents. An estimate for systemic exposure of humans from the use of fragranced cosmetic products is 0.04 mg/kg BW/day, assuming complete dermal penetration. The use of coumarin as a food additive was banned by the FDA in 1954 based on reports of hepatotoxicity in rats. Due to its potential hepatotoxic effects in humans, the European Commission restricted coumarin from naturals as a direct food additive to 2 mg/kg food/day, with exceptions granting higher levels for alcoholic beverages, caramel, chewing gum, and certain traditional foods. In addition to human exposure to coumarin from dietary sources and consumer products, coumarin is also used clinically as an antineoplastic and for the treatment of lymphedema and venous insufficiency. Exposure ranges from 11 mg/day for consumption of natural food ingredients to 7 g/day following clinical administration. Although adverse effects in humans following coumarin exposure are rare, and only associated with clinical doses, recent evidence indicates coumarin causes liver tumors in rats and mice and Clara cell toxicity and lung tumors in mice. The multiple effects as well as the ongoing human exposure to coumarin have resulted in a significant research effort focused on understanding the mechanism of coumarin induced toxicity/carcinogenicity and its human relevance. These investigations have revealed significant species differences in coumarin metabolism and toxicity such that the mechanism of coumarin induced effects in rodents, and the relevance of these findings for the safety assessment of coumarin exposure in humans are now better understood. In October 2004, the European Food Safety Authority (EFSA, 2004) reviewed coumarin to establish a tolerable daily intake (TDI) in foods. EFSA issued an opinion indicating that coumarin is not genotoxic, and that a threshold approach to safety assessment was most appropriate. EFSA recommended a TDI of 0 to 0.1 mg/kg BW/day. Including dietary contributions, the total human exposure is estimated to be 0.06 mg/kg/day. As a pharmaceutical, coumarin has been used in diverse applications with a wide variety of dosing regimens. Unlike coumadin and ... Coumarin belongs to the class of chemicals known as chromenones. Specifically it is a chromenone having the keto group located at the 2-position. A chromenone is a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain forming a second six-membered heterocycle that shares two carbons with the benzene ring. Coumarin is also described as a benzopyrone and is considered as a lactone. Coumarin is a colorless crystalline solid with a bitter taste and sweet odor resembling the scent of vanilla or the scent of newly-mowed or recently cut hay. It is a chemical poison found in many plants where it may serve as a chemical defense against predators. Coumarin occurs naturally in many plants and foods such as the tonka bean, woodruff, bison grass, cassia (bastard cinnamon or Chinese cinnamon), cinnamon, melilot (sweet clover), green tea, peppermint, celery, bilberry, lavender, honey (derived both from sweet clover and lavender), and carrots, as well as in beer, tobacco, wine, and other foodstuffs. Coumarin concentrations in these plants, spices, and foods range from <1 mg/kg in celery, to 7000 mg/kg in cinnamon, and up to 87,000 mg/kg in cassia. An estimate of human exposure to coumarin from the diet has been calculated to be 0.02 mg/kg/day. Coumarin is used as an additive in perfumes and fragranced consumer products at concentrations ranging from <0.5\\\\% To 6.4\\\\% In fine fragrances to <0.01\\\\% In detergents. An estimate for systemic exposure of humans from the use of fragranced cosmetic products is 0.04 mg/kg BW/day, assuming complete dermal penetration. The use of coumarin as a food additive was banned by the FDA in 1954 based on reports of hepatotoxicity in rats. It has clinical value as the precursor for several anticoagulants, notably warfarin. Coumarins, as a class, are comprised of numerous naturally occurring benzo-alpha-pyrone compounds with important and diverse physiological activities. Due to its potential hepatotoxic effects in humans, the European Commission restricted coumarin from naturals as a direct food additive to 2 mg/kg food/day, with exceptions granting higher levels for alcoholic beverages, caramel, chewing gum, and certain traditional foods. In addition to human exposure to coumarin from dietary sources and consumer products, coumarin is also used clinically as an antineoplastic and for the treatment of lymphedema and venous insufficiency. Exposure ranges from 11 mg/day for consumption of natural food ingredients to 7 g/day following clinical administration. Although adverse effects in humans following coumarin exposure are rare, and only associated with clinical doses, recent evidence indicates coumarin causes liver tumors in rats and mice and Clara cell toxicity and lung tumors in mice. The multiple effects as well as the ongoing human exposure to coumarin have resulted in a significant research effort focused on understanding the mechanism of coumarin induced toxicity/carcinogenicity and its human relevance. These investigations have revealed significant species differences in coumarin metabolism and toxicity such that the mechanism of coumarin induced effects in rodents, and the relevance of these findings for the safety assessment of coumarin exposure in humans are now better understood. In October 2004, the European Food Safety Authority (EFSA, 2004) reviewed coumarin to establish a tolerable daily intake (TDI) in foods. EFSA issued an opinion indicating that coumarin is not genotoxic, and that a threshold approach to safety assessment was most appropriate. EFSA recommended a TDI of 0 to 0.1 Mg/kg BW/day. Including dietary contributions, the total human exposure is estimated to be 0.06 Mg/kg/day. As a pharmaceutical, coumarin has been used in diverse applications with a wide variety of dosing regimens. Unlike coumadin and other coumarin derivatives, coumarin has no anti-coagulant activity. However, at low doses (typically 7 to 10 mg/day), coumarin has been used as a venotonic to promote... C78275 - Agent Affecting Blood or Body Fluid > C263 - Anticoagulant Agent A chromenone having the keto group located at the 2-position. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS [Raw Data] CB013_Coumarin_pos_20eV_CB000008.txt [Raw Data] CB013_Coumarin_pos_30eV_CB000008.txt [Raw Data] CB013_Coumarin_pos_10eV_CB000008.txt [Raw Data] CB013_Coumarin_pos_50eV_CB000008.txt [Raw Data] CB013_Coumarin_pos_40eV_CB000008.txt Coumarin is the primary bioactive ingredient in Radix Glehniae, named Beishashen in China, which possesses many pharmacological activities, including anticancer, anti-inflammation and antivirus activities. Coumarin is the primary bioactive ingredient in Radix Glehniae, named Beishashen in China, which possesses many pharmacological activities, including anticancer, anti-inflammation and antivirus activities.

Camphor

C10H16O (152.1201)

Camphor appears as a colorless or white colored crystalline powder with a strong mothball-like odor. About the same density as water. Emits flammable vapors above 150 °F. Used to make moth proofings, pharmaceuticals, and flavorings. Camphor is a cyclic monoterpene ketone that is bornane bearing an oxo substituent at position 2. A naturally occurring monoterpenoid. It has a role as a plant metabolite. It is a bornane monoterpenoid and a cyclic monoterpene ketone. Camphor is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available. A bicyclic monoterpene ketone found widely in plants, especially CINNAMOMUM CAMPHORA. It is used topically as a skin antipruritic and as an anti-infective agent. A cyclic monoterpene ketone that is bornane bearing an oxo substituent at position 2. A naturally occurring monoterpenoid. C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000890 - Anti-Infective Agents relative retention time with respect to 9-anthracene Carboxylic Acid is 0.986 Camphor ((±)-Camphor) is a topical anti-infective and anti-pruritic and internally as a stimulant and carminative. However, Camphor is poisonous when ingested. Antiviral, antitussive, and anticancer activities[1]. Camphor is a TRPV3 agonist[2]. Camphor ((±)-Camphor) is a topical anti-infective and anti-pruritic and internally as a stimulant and carminative. However, Camphor is poisonous when ingested. Antiviral, antitussive, and anticancer activities[1]. Camphor is a TRPV3 agonist[2].

Luteolin

C15H10O6 (286.0477)

Luteolin is a naturally occurring flavonoid. (PMID:17168665). The flavonoids are polyphenolic compounds found as integral components of the human diet. They are universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. An impressive body of information exists on the antitumoral action of plant flavonoids. In vitro work has concentrated on the direct and indirect actions of flavonoids on tumor cells, and has found a variety of anticancer effects such as cell growth and kinase activity inhibition, apoptosis induction, suppression of the secretion of matrix metalloproteinases and of tumor invasive behavior. Furthermore, some studies have reported the impairment of in vivo angiogenesis by dietary flavonoids. Experimental animal studies indicate that certain dietary flavonoids possess antitumoral activity. The hydroxylation pattern of the B ring of the flavones and flavonols, such as luteolin seems to critically influence their activities, especially the inhibition of protein kinase activity and antiproliferation. The different mechanisms underlying the potential anticancer action of plant flavonoids await further elucidation. Certain dietary flavonols and flavones targeting cell surface signal transduction enzymes, such as protein tyrosine and focal adhesion kinases, and the processes of angiogenesis appear to be promising candidates as anticancer agents. Further in vivo studies of these bioactive constituents is deemed necessary in order to develop flavonoid-based anticancer strategies. In view of the increasing interest in the association between dietary flavonoids and cancer initiation and progression, this important field is likely to witness expanded effort and to attract and stimulate further vigorous investigations (PMID:16097445). Luteolin is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. It has a role as an EC 2.3.1.85 (fatty acid synthase) inhibitor, an antineoplastic agent, a vascular endothelial growth factor receptor antagonist, a plant metabolite, a nephroprotective agent, an angiogenesis inhibitor, a c-Jun N-terminal kinase inhibitor, an anti-inflammatory agent, an apoptosis inducer, a radical scavenger and an immunomodulator. It is a 3-hydroxyflavonoid and a tetrahydroxyflavone. It is a conjugate acid of a luteolin-7-olate. Luteolin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Luteolin is a naturally-occurring flavonoid, with potential anti-oxidant, anti-inflammatory, apoptosis-inducing and chemopreventive activities. Upon administration, luteolin scavenges free radicals, protects cells from reactive oxygen species (ROS)-induced damage and induces direct cell cycle arrest and apoptosis in tumor cells. This inhibits tumor cell proliferation and suppresses metastasis. 5,7,3,4-tetrahydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. Flavone v. widespread in plant world; found especies in celery, peppermint, rosemary, thyme and Queen Annes Lace leaves (wild carrot). Potential nutriceutical. Luteolin is found in many foods, some of which are soy bean, ginger, abalone, and swiss chard. Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 361; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 48 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].

Maslinic acid

C30H48O4 (472.3552)

Maslinic acid is a compound derived from dry olive-pomace oil (an olive skin wax) which is a byproduct of olive oil extraction. It is a member of the group of triterpenes known as oleananes.; Maslinic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Maslinic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. (PMID: 17292619) Maslinic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Maslinic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. (PMID: 17292619). Maslinic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity. It has a role as an antioxidant, an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid and a dihydroxy monocarboxylic acid. It derives from a hydride of an oleanane. Maslinic acid is a natural product found in Chaenomeles speciosa, Salvia tomentosa, and other organisms with data available. See also: Centaurium erythraea whole (part of). A pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity. Maslinic acid can inhibit the DNA-binding activity of NF-κB p65 and abolish the phosphorylation of IκB-α, which is required for p65 activation. Maslinic acid can inhibit the DNA-binding activity of NF-κB p65 and abolish the phosphorylation of IκB-α, which is required for p65 activation.

Genkwanin

C16H12O5 (284.0685)

Genkwanin, also known as 5,4-dihydroxy-7-methoxyflavone or 7-methylapigenin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, genkwanin is considered to be a flavonoid lipid molecule. Genkwanin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Genkwanin is a bitter tasting compound and can be found in a number of food items such as winter savory, sweet basil, rosemary, and common sage, which makes genkwanin a potential biomarker for the consumption of these food products. Genkwanin is an O-methylated flavone, a type of flavonoid. It can be found in the seeds of Alnus glutinosa, and the leaves of the ferns Notholaena bryopoda and Asplenium normale . Genkwanin is a major non-glycosylated flavonoid with anti-flammatory activities. Genkwanin is a major non-glycosylated flavonoid with anti-flammatory activities.

Ursolic acid

C30H48O3 (456.3603)

Ursolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. Ursolic acid (UA), a pentacyclic triterpene acid, has been isolated from many kinds of medicinal plants, such as Eriobotrya japonica, Rosmarinns officinalis, Melaleuca leucadendron, Ocimum sanctum and Glechoma hederaceae. UA has been reported to produce antitumor activities and antioxidant activity, and is reported to have an antioxidant activity. UA may play an important role in regulating the apoptosis induced by high glucose presumably through scavenging of ROS (reactive oxygen species). It has been found recently that ursolic acid treatment affects growth and apoptosis in cancer cells. (PMID: 15994040, 17516235, 17213663). Ursolic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite and a geroprotector. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of an ursane. Ursolic acid is a natural product found in Gladiolus italicus, Freziera, and other organisms with data available. Ursolic Acid is a pentacyclic triterpenoid found in various fruits, vegetables and medicinal herbs, with a variety of potential pharmacologic activities including anti-inflammatory, antioxidative, antiviral, serum lipid-lowering, and antineoplastic activities. Upon administration, ursolic acid may promote apoptosis and inhibit cancer cell proliferation through multiple mechanisms. This may include the regulation of mitochondrial function through various pathways including the ROCK/PTEN and p53 pathways, the suppression of the nuclear factor-kappa B (NF-kB) pathways, and the increase in caspase-3, caspase-8 and caspase-9 activities. See also: Holy basil leaf (part of); Jujube fruit (part of); Lagerstroemia speciosa leaf (part of). D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. C274 - Antineoplastic Agent > C129839 - Apoptotic Pathway-targeting Antineoplastic Agent Found in wax of apples, pears and other fruits. V. widely distributed in plants D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics C26170 - Protective Agent > C275 - Antioxidant D000893 - Anti-Inflammatory Agents D000890 - Anti-Infective Agents D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors 3-Epiursolic Acid is a triterpenoid that can be isolated from Eriobotrya japonica, acts as a competitive inhibitor of cathepsin L (IC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B[1]. 3-Epiursolic Acid is a triterpenoid that can be isolated from Eriobotrya japonica, acts as a competitive inhibitor of cathepsin L (IC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B[1]. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.

Cosmosiin

C21H20O10 (432.1056)

Cosmosiin, also known as apigenin 7-O-glucoside or apigetrin, is a member of the class of compounds known as flavonoid-7-O-glycosides. Flavonoid-7-O-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Cosmosiin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cosmosiin can be found in a number of food items, such as common thyme, white lupine, common oregano, and orange mint. Cosmosiin can also be found in dandelion coffee and in Teucrium gnaphalodes (Wikipedia). Cosmosiin can also be found plants such as wild celery and anise. Cosmosiin has been shown to exhibit anti-platelet function (PMID: 21834233). Apigenin 7-O-beta-D-glucoside is a glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as a non-steroidal anti-inflammatory drug, a metabolite and an antibacterial agent. It is a beta-D-glucoside, a dihydroxyflavone, a glycosyloxyflavone and a monosaccharide derivative. It is functionally related to an apigenin. It is a conjugate acid of an apigenin 7-O-beta-D-glucoside(1-). It is an enantiomer of an apigenin 7-O-beta-L-glucoside. Cosmosiin is a natural product found in Galeopsis tetrahit, Carex fraseriana, and other organisms with data available. See also: Chamomile (part of). Apiumetrin, also known as 7-O-beta-D-glucosyl-5,7,4-trihydroxyflavone or cosmosiin, is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Apiumetrin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Apiumetrin can be found in wild celery, which makes apiumetrin a potential biomarker for the consumption of this food product. Acquisition and generation of the data is financially supported in part by CREST/JST. Annotation level-1 Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2]. Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2].

Apigenin

C15H10O5 (270.0528)

Apigenin is a trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. It has a role as a metabolite and an antineoplastic agent. It is a conjugate acid of an apigenin-7-olate. Apigenin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter and the increase in hINV promoter activity. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes. (A7924). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin. (A7925). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis. (A7926). 5,7,4-trihydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, and MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes (PMID: 16982614). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin (PMID: 16844095). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis (PMID: 16648565). Flavone found in a wide variety of foodstuffs; buckwheat, cabbage, celeriac, celery, lettuce, oregano, parsley, peppermint, perilla, pummelo juice, thyme, sweet potatoes, green tea and wild carrot [DFC] A trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8558; ORIGINAL_PRECURSOR_SCAN_NO 8556 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5097; ORIGINAL_PRECURSOR_SCAN_NO 5094 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5096; ORIGINAL_PRECURSOR_SCAN_NO 5093 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8561; ORIGINAL_PRECURSOR_SCAN_NO 8559 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5082; ORIGINAL_PRECURSOR_SCAN_NO 5079 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5104; ORIGINAL_PRECURSOR_SCAN_NO 5099 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8572; ORIGINAL_PRECURSOR_SCAN_NO 8570 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8556; ORIGINAL_PRECURSOR_SCAN_NO 8554 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5085; ORIGINAL_PRECURSOR_SCAN_NO 5082 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8554; ORIGINAL_PRECURSOR_SCAN_NO 8550 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8540; ORIGINAL_PRECURSOR_SCAN_NO 8539 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5090; ORIGINAL_PRECURSOR_SCAN_NO 5089 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB002_Apigenin_pos_10eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_40eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_20eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_30eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_50eV_CB000005.txt [Raw Data] CB002_Apigenin_neg_40eV_000005.txt [Raw Data] CB002_Apigenin_neg_20eV_000005.txt [Raw Data] CB002_Apigenin_neg_10eV_000005.txt [Raw Data] CB002_Apigenin_neg_50eV_000005.txt CONFIDENCE standard compound; INTERNAL_ID 151 [Raw Data] CB002_Apigenin_neg_30eV_000005.txt CONFIDENCE standard compound; ML_ID 26 Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

Caffeic acid

C9H8O4 (180.0423)

Caffeic acid is a hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common. It has a role as a plant metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antioxidant and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a hydroxycinnamic acid and a member of catechols. Caffeic Acid is a natural product found in Pavetta indica, Eupatorium cannabinum, and other organisms with data available. Caffeic Acid is an orally bioavailable, hydroxycinnamic acid derivative and polyphenol, with potential anti-oxidant, anti-inflammatory, and antineoplastic activities. Upon administration, caffeic acid acts as an antioxidant and prevents oxidative stress, thereby preventing DNA damage induced by free radicals. Caffeic acid targets and inhibits the histone demethylase (HDM) oncoprotein gene amplified in squamous cell carcinoma 1 (GASC1; JMJD2C; KDM4C) and inhibits cancer cell proliferation. GASC1, a member of the KDM4 subgroup of Jumonji (Jmj) domain-containing proteins, demethylates trimethylated lysine 9 and lysine 36 on histone H3 (H3K9 and H3K36), and plays a key role in tumor cell development. Caffeic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Arctium lappa Root (part of); Comfrey Leaf (part of) ... View More ... 3,4-Dihydroxy-trans-cinnamate, also known as trans-Caffeate, is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). trans-Caffeic acid is found in many foods, some of which are flaxseed, cereal and cereal products, common grape, fruits, and common sage. It is also found in wine and coffee in free and conjugated forms. Caffeic acid (CAS: 331-39-5) is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). Caffeic acid has been found to be a microbial metabolite of Escherichia (PMID: 28396925). Caffeic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=331-39-5 (retrieved 2024-06-28) (CAS RN: 331-39-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

Herniarin

C10H8O3 (176.0473)

Herniarin, also known as 7-methoxycoumarin or ayapanin, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Herniarin is a sweet, balsamic, and tonka tasting compound. Herniarin has been detected, but not quantified, in several different foods, such as barley, tarragons, roman camomiles, fruits, and wild celeries. This could make herniarin a potential biomarker for the consumption of these foods. Herniarin is a member of the class of coumarins that is coumarin substituted by a methoxy group at position 7. It has a role as a fluorochrome. 7-Methoxycoumarin is a natural product found in Haplopappus multifolius, Herniaria hirsuta, and other organisms with data available. See also: Chamomile (part of); Glycyrrhiza Glabra (part of). Present in Prunus mahaleb (mahaleb cherry). Herniarin is found in many foods, some of which are caraway, wild celery, barley, and fruits. A member of the class of coumarins that is coumarin substituted by a methoxy group at position 7. Herniarin is a natural coumarin occurs in some flowering plants, with antitumor effect. Herniarin is a natural coumarin occurs in some flowering plants, with antitumor effect.

Vitexin 6'-O-malonyl 2'-O-xyloside

C21H20O10 (432.1056)

Vitexin 6-o-malonyl 2-o-xyloside, also known as apigenin 8-C-glucoside or 8-glycosyl-apigenin, is a member of the class of compounds known as flavonoid 8-c-glycosides. Flavonoid 8-c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vitexin 6-o-malonyl 2-o-xyloside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Vitexin 6-o-malonyl 2-o-xyloside can be synthesized from apigenin. Vitexin 6-o-malonyl 2-o-xyloside is also a parent compound for other transformation products, including but not limited to, vitexin 2-O-beta-L-rhamnoside, 7-O-methylvitexin 2-O-beta-L-rhamnoside, and vitexin 2-O-beta-D-glucoside. Vitexin 6-o-malonyl 2-o-xyloside can be found in common beet, which makes vitexin 6-o-malonyl 2-o-xyloside a potential biomarker for the consumption of this food product. Vitexin, also known as apigenin 8-C-glucoside or 8-glycosylapigenin, belongs to the class of organic compounds known as flavonoid 8-C-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vitexin is also described as an apigenin flavone glucoside. Vitexin has been found in passion flower, chasteberry, bamboo leaves, millet and Hawthorn. Vitexin has shown a wide range of pharmacological effects, such as antioxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects (PMID: 27693342). Vitexin has also been shown to directly inhibit thyroid peroxidase and potentially contributes to goiter (PMID: 1696490). It is sometimes called a goitrogen. Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CBA68_Vitexin_neg_10eV.txt [Raw Data] CBA68_Vitexin_neg_30eV.txt [Raw Data] CBA68_Vitexin_pos_20eV.txt [Raw Data] CBA68_Vitexin_neg_50eV.txt [Raw Data] CBA68_Vitexin_neg_40eV.txt [Raw Data] CBA68_Vitexin_pos_40eV.txt [Raw Data] CBA68_Vitexin_pos_30eV.txt [Raw Data] CBA68_Vitexin_pos_10eV.txt [Raw Data] CBA68_Vitexin_neg_20eV.txt Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2]. Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2].

Luteolin 7-glucoside

C21H20O11 (448.1006)

Luteolin 7-O-beta-D-glucoside is a glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as an antioxidant and a plant metabolite. It is a beta-D-glucoside, a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a luteolin. It is a conjugate acid of a luteolin 7-O-beta-D-glucoside(1-). Cynaroside is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. See also: Cynara scolymus leaf (part of); Lonicera japonica flower (part of); Chamaemelum nobile flower (part of). Luteolin 7-glucoside is found in anise. Luteolin 7-glucoside is a constituent of the leaves of Capsicum annuum (red pepper).Cynaroside is a flavone, a flavonoid-like chemical compound. It is a 7-O-glucoside of luteolin and can be found in dandelion coffee, in Ferula varia and F. foetida in Campanula persicifolia and C. rotundifolia and in Cynara scolymus (artichoke) A glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. Constituent of the leaves of Capsicum annuum (red pepper) Cynaroside (Luteolin 7-glucoside) is a flavonoid compound that exhibits anti-oxidative capabilities. Cynaroside is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 32 nM. Cynaroside also is a promising inhibitor for H2O2-induced apoptosis, has cytoprotection against oxidative stress-induced cardiovascular diseases. Cynaroside also has antibacterial, antifungal and anticancer activities, antioxidant and anti-inflammatory activities[1][3][4][5].

Ferulic acid

C10H10O4 (194.0579)

trans-Ferulic acid is a highly abundant phenolic phytochemical which is present in plant cell walls. Ferulic acid is a phenolic acid that can be absorbed by the small intestine and excreted through the urine. It is one of the most abundant phenolic acids in plants, varying from 5 g/kg in wheat bran to 9 g/kg in sugar-beet pulp and 50 g/kg in corn kernel. It occurs primarily in seeds and leaves both in its free form (albeit rarely) and covalently linked to lignin and other biopolymers. It is usually found as ester cross-links with polysaccharides in the cell wall, such as arabinoxylans in grasses, pectin in spinach and sugar beet, and xyloglucans in bamboo. It also can cross-link with proteins. Due to its phenolic nucleus and an extended side chain conjugation (carbohydrates and proteins), it readily forms a resonance-stabilized phenoxy radical which accounts for its potent antioxidant potential. Food supplementation with curcumin and ferulic acid is considered a nutritional approach to reducing oxidative damage and amyloid pathology in Alzheimer disease (PMID:17127365, 1398220, 15453708, 9878519). Ferulic acid can be found in Pseudomonas and Saccharomyces (PMID:8395165). Ferulic acid is a ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring. It has a role as an antioxidant, a MALDI matrix material, a plant metabolite, an anti-inflammatory agent, an apoptosis inhibitor and a cardioprotective agent. It is a conjugate acid of a ferulate. Ferulic acid is a natural product found in Haplophyllum griffithianum, Visnea mocanera, and other organisms with data available. Ferulic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Angelica sinensis root (part of). Widely distributed in plants, first isolated from Ferula foetida (asafoetida). Antioxidant used to inhibit oxidn. of fats, pastry products, etc. Antifungal agent used to prevent fruit spoilage. trans-Ferulic acid is found in many foods, some of which are deerberry, peach, shea tree, and common bean. A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D002491 - Central Nervous System Agents > D000700 - Analgesics D000975 - Antioxidants > D016166 - Free Radical Scavengers D006401 - Hematologic Agents > D000925 - Anticoagulants D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID H074 (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively.

3,7-Dimethyl-1,6-octadien-3-ol

C10H18O (154.1358)

3,7-Dimethyl-1,6-octadien-3-ol, also known simply as linalool is a naturally occurring terpene alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Linalool has a role as a plant metabolite, a volatile oil component, an antimicrobial agent and a fragrance. There are two stereoisomers of Linalool ‚Äö√Ñ√¨ (S)-linalool and (R)-linalool. Linalool is used as a scent in 60\\\\\% to 80\\\\\% of perfumed hygiene products and cleaning agents including soaps, detergents, shampoos, and lotions. Linalool is also used by pest professionals as a flea, fruit fly, and cockroach insecticide. Linalool is found in more than 200 different species of plants, including many flowers and spice plants. (S)-linalool is found, for example, as a major constituent of the essential oils of coriander (Coriandrum sativum L.), cymbopogon (Cymbopogon martini var. martinii), and sweet orange (Citrus sinensis) flowers. (R)-linalool is present in lavender (Lavandula officinalis), bay laurel (Laurus nobilis), and sweet basil (Ocimum basilicum), among others. Linalool is also found in plants from the Lamiaceae family (mint and other herbs), Lauraceae (laurels, cinnamon, rosewood), Cinnamomum tamala, Solidago Meyen, Artemisia vulgaris (mugwort), Humulus lupulus. Linalool is also one of several monoterpenes that are found in cannabis plants (PMID:6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. Like the majority of monoterpenes, linalool starts with the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl pyrophosphate (GPP) (PMID:7640522 ). Linalool is then synthesized with the aid of linalool synthase (LIS) (PMID:12572612 ). Linalool has a citrus, floral, rose, woody aroma and a citrus, orange, waxy taste. Linalool is found in a few different foods and spices, such as spearmints, corianders, common thymes, limes, grapes, lemons, grapefruit, oranges, pineapples, blackcurrants, basil, and common oregano. This could make, Linalool a potential biomarker for the consumption of these foods. Linalool is also synthesized, de novo, by yeast (C. cerevisiae) and may contribute to the floral tones found in some wines (PMID:15668008 ). Linalool is a monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum. It has a role as a plant metabolite, a volatile oil component, an antimicrobial agent and a fragrance. It is a tertiary alcohol and a monoterpenoid. Linalool is a natural product found in Nepeta nepetella, Teucrium montanum, and other organisms with data available. 3,7-Dimethyl-1,6-octadien-3-ol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Cinnamon Leaf Oil (part of); Clary Sage Oil (part of); Cannabis sativa subsp. indica top (part of) ... View More ... A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum. Flavouring agent. Widespread natural occurrence as the optically active and racemic forms in over 200 essential oilsand is) also present in numerous fruits. D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals Linalool is natural monoterpene in essential olis of coriander, acts as a competitive antagonist of Nmethyl d-aspartate (NMDA) receptor, with anti-tumor, anti-cardiotoxicity activity[1].Linalool is a PPARα ligand that reduces plasma TG levels and rewires the hepatic transcriptome and plasma metabolome[2]. Linalool is a natural monoterpene which is a competitive NMDA receptor antagonist. Linalool is orally active and crosses the blood-brain barrier. Linalool has anticancer, antibacterial, anti-inflammatory, neuroprotective, anxiolytic, antidepressant, anti-stress, cardioprotective, hepatoprotective, nephroprotective and pulmonary protective activities[1][2][3][4][5]. Linalool is natural monoterpene in essential olis of coriander, acts as a competitive antagonist of Nmethyl d-aspartate (NMDA) receptor, with anti-tumor, anti-cardiotoxicity activity[1].Linalool is a PPARα ligand that reduces plasma TG levels and rewires the hepatic transcriptome and plasma metabolome[2].

Menthol

C10H20O (156.1514)

D,l-menthol is a white crystalline solid with a peppermint odor and taste. (NTP, 1992) (-)-menthol is a p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer. It has a role as an antipruritic drug, an antitussive and an antispasmodic drug. It is an enantiomer of a (+)-menthol. Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. Forming clear or white waxy, crystalline substance, menthol is typically solid at room temperature. (-)-Menthol is the naturally-occurring and main form of menthol, and is assigned the (1R,2S,5R) configuration. Menthol mediates anesthetic properties and anti-irritating properties locally, thus it is widely used to relieve minor throat irritations. l-Menthol is a natural product found in Punica granatum, Mentha arvensis, and other organisms with data available. Levomenthol is a levo isomer of menthol, an organic compound made synthetically or obtained from peppermint or mint oils with flavoring and local anesthetic properties. When added to pharmaceuticals and foods, menthol functions as a fortifier for peppermint flavors. It also has a counterirritant effect on skin and mucous membranes, thereby producing a local analgesic or anesthetic effect. Menthol is an alcohol produced from mint oils or prepared synthetically. Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (-)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation. Menthol is an alcohol produced from mint oils or prepared synthetically. Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (-)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation. Present in large amts. in peppermint oil (Mentha piperita), also in other Mentha subspecies. It is used in confectionery and perfumery. Flavouring agent A p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer. C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent D003879 - Dermatologic Agents > D000982 - Antipruritics (-)-Menthol is a key component of peppermint oil that binds and activates transient receptor potential melastatin 8 (TRPM8), a Ca2+-permeable nonselective cation channel, to increase [Ca2+]i[1]. Antitumor activity[1]. (-)-Menthol is a key component of peppermint oil that binds and activates transient receptor potential melastatin 8 (TRPM8), a Ca2+-permeable nonselective cation channel, to increase [Ca2+]i[1]. Antitumor activity[1]. (-)-Menthol is a key component of peppermint oil that binds and activates transient receptor potential melastatin 8 (TRPM8), a Ca2+-permeable nonselective cation channel, to increase [Ca2+]i[1]. Antitumor activity[1]. (-)-Menthol is a key component of peppermint oil that binds and activates transient receptor potential melastatin 8 (TRPM8), a Ca2+-permeable nonselective cation channel, to increase [Ca2+]i[1]. Antitumor activity[1]. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1]. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1]. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1]. Menthol is a natural analgesic compound. Menthol could cause a feeling of coolness due to stimulation of ‘cold’ receptors by inhibiting Ca++ currents of neuronal membranes[1]. Menthol is a natural analgesic compound. Menthol could cause a feeling of coolness due to stimulation of ‘cold’ receptors by inhibiting Ca++ currents of neuronal membranes[1].

Palmitic acid

C16H32O2 (256.2402)

Palmitic acid, also known as palmitate or hexadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, palmitic acid is considered to be a fatty acid lipid molecule. Palmitic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Palmitic acid can be found in a number of food items such as sacred lotus, spinach, shallot, and corn salad, which makes palmitic acid a potential biomarker for the consumption of these food products. Palmitic acid can be found primarily in most biofluids, including feces, sweat, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Palmitic acid exists in all living species, ranging from bacteria to humans. In humans, palmitic acid is involved in several metabolic pathways, some of which include alendronate action pathway, rosuvastatin action pathway, simvastatin action pathway, and cerivastatin action pathway. Palmitic acid is also involved in several metabolic disorders, some of which include hypercholesterolemia, familial lipoprotein lipase deficiency, ethylmalonic encephalopathy, and carnitine palmitoyl transferase deficiency (I). Moreover, palmitic acid is found to be associated with schizophrenia. Palmitic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Palmitic acid can also be found in meats, cheeses, butter, and dairy products. Palmitate is the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4) . Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation (DrugBank). Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30\\\% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent. Hexadecanoic acid is a straight-chain, sixteen-carbon, saturated long-chain fatty acid. It has a role as an EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a hexadecanoate. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. Palmitic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Palmitic Acid is a saturated long-chain fatty acid with a 16-carbon backbone. Palmitic acid is found naturally in palm oil and palm kernel oil, as well as in butter, cheese, milk and meat. Palmitic acid, or hexadecanoic acid is one of the most common saturated fatty acids found in animals and plants, a saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. It occurs in the form of esters (glycerides) in oils and fats of vegetable and animal origin and is usually obtained from palm oil, which is widely distributed in plants. Palmitic acid is used in determination of water hardness and is an active ingredient of *Levovist*TM, used in echo enhancement in sonographic Doppler B-mode imaging and as an ultrasound contrast medium. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. A straight-chain, sixteen-carbon, saturated long-chain fatty acid. Palmitic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-10-3 (retrieved 2024-07-01) (CAS RN: 57-10-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Betulin

C30H50O2 (442.3811)

Betulin is found in black elderberry. Betulin is a constituent of Corylus avellana (filbert) and Vicia faba. Betulin (lup-20(29)-ene-3 ,28-diol) is an abundant naturally occurring triterpene. It is commonly isolated from the bark of birch trees and forms up to 30\\\\\% of the dry weight of the extractive. The purpose of the compound in the bark is not known. It can be converted to betulinic acid (the alcohol group replaced by a carboxylic acid group), which is biologically more active than betulin itself. Chemically, betulin is a triterpenoid of lupane structure. It has a pentacyclic ring structure, and hydroxyl groups in positions C3 and C28 Betulin is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents. It has a role as a metabolite, an antiviral agent, an analgesic, an anti-inflammatory agent and an antineoplastic agent. It is a pentacyclic triterpenoid and a diol. It derives from a hydride of a lupane. Betulin is a natural product found in Diospyros morrisiana, Euonymus carnosus, and other organisms with data available. A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents. Constituent of Corylus avellana (filbert) and Vicia faba Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line.

Betulinic acid

C30H48O3 (456.3603)

Betulinic acid is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an antimalarial, an anti-inflammatory agent, an antineoplastic agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane. Betulinic Acid has been used in trials studying the treatment of Dysplastic Nevus Syndrome. Betulinic acid is a natural product found in Ficus auriculata, Gladiolus italicus, and other organisms with data available. Betulinic Acid is a pentacyclic lupane-type triterpene derivative of betulin (isolated from the bark of Betula alba, the common white birch) with antiinflammatory, anti-HIV and antineoplastic activities. Betulinic acid induces apoptosis through induction of changes in mitochondrial membrane potential, production of reactive oxygen species, and opening of mitochondrial permeability transition pores, resulting in the release of mitochondrial apogenic factors, activation of caspases, and DNA fragmentation. Although originally thought to exhibit specific cytotoxicity against melanoma cells, this agent has been found to be cytotoxic against non-melanoma tumor cell types including neuroectodermal and brain tumor cells. A lupane-type triterpene derivative of betulin which was originally isolated from BETULA or birch tree. It has anti-inflammatory, anti-HIV and antineoplastic activities. See also: Jujube fruit (part of); Paeonia lactiflora root (part of). Betulinic acid is found in abiyuch. Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis. Controversial is a role of p53 in betulinic acid-induced apoptosis. Fulda suggested p53-independent mechanism of the apoptosis, basing on fact of no accumulation of wild-type p53 detected upon treatment with the betulinic acid, whereas wild-type p53 protein strongly increased after treatment with doxorubicin. The suggestion is supported by study of Raisova. On the other hand Rieber suggested that betulinic acid exerts its inhibitory effect on human metastatic melanoma partly by increasing p53 A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. C308 - Immunotherapeutic Agent > C2139 - Immunostimulant Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Epibetulinic acid exhibits potent inhibitory effects on NO and prostaglandin E2 (PGE2) production in mouse macrophages (RAW 264.7) stimulated with bacterial endotoxin with IC50s of 0.7 and 0.6 μM, respectively. Anti-inflammatory activity[1].

Oleanolic acid

C30H48O3 (456.3603)

Oleanolic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Oleanolic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. Oleanolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. (PMID:17292619, 15522132, 15994040). Oleanolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an oleanolate. It derives from a hydride of an oleanane. Oleanolic acid is a natural product found in Ophiopogon japonicus, Freziera, and other organisms with data available. A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. See also: Holy basil leaf (part of); Jujube fruit (part of); Paeonia lactiflora root (part of) ... View More ... Occurs as glycosides in cloves (Syzygium aromaticum), sugar beet (Beta vulgaris), olive leaves, etc. Very widely distributed aglycone A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. [Raw Data] CBA90_Oleanolic-acid_neg_50eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_20eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_10eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_30eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_40eV.txt Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.

beta-Sitosterol 3-O-beta-D-galactopyranoside

C35H60O6 (576.439)

Daucosterol is a steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa. It has a role as a plant metabolite. It is a steroid saponin, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a sitosterol. It derives from a hydride of a stigmastane. Sitogluside is a natural product found in Ophiopogon intermedius, Ophiopogon jaburan, and other organisms with data available. beta-Sitosterol 3-O-beta-D-galactopyranoside is found in herbs and spices. beta-Sitosterol 3-O-beta-D-galactopyranoside is a constituent of Hibiscus sabdariffa (roselle) leaves. C308 - Immunotherapeutic Agent Daucosterol is a natural sterol compound. Daucosterol is a natural sterol compound.

(-)-Sabinene

C10H16 (136.1252)

Sabinene (CAS: 3387-41-5) belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, sabinene is considered to be an isoprenoid lipid molecule. Sabinene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (-)-Sabinene is found in herbs and spices and is a constituent of Laurus nobilis (bay laurel). Constituent of Laurus nobilis (bay laurel) and some other plants. (-)-4(10)-Thujene is found in sweet bay and herbs and spices. Sabinene is a thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species. It has a role as a plant metabolite. Black pepper allergenic extract is used in allergenic testing. Laurus nobilis allergenic extract is used in allergenic testing. Nutmeg allergenic extract is used in allergenic testing. Sabinene is a natural product found in Teucrium montanum, Xylopia aromatica, and other organisms with data available. Carrot Seed Oil is the oil extracted from the seeds of Daucus carota. Carrot seed oil is primarily used in skin treatment preparations. Acquisition and generation of the data is financially supported in part by CREST/JST. Sabinene is an naturally occurring bicyclic monoterpene which can be used as flavorings, perfume additives, fine chemicals, and advanced biofuels. Sabinene is also an orally active compound to attenuates skeletal muscle atrophy and regulates ROS-mediated MAPK/MuRF-1 pathways[1][2]. Sabinene is an naturally occurring bicyclic monoterpene which can be used as flavorings, perfume additives, fine chemicals, and advanced biofuels. Sabinene is also an orally active compound to attenuates skeletal muscle atrophy and regulates ROS-mediated MAPK/MuRF-1 pathways[1][2].

Chrysoeriol

C16H12O6 (300.0634)

Chrysoeriol, also known as 3-O-methylluteolin, belongs to the class of organic compounds known as 3-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, chrysoeriol is considered to be a flavonoid lipid molecule. Chrysoeriol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Chrysoeriol is a bitter-tasting compound. Outside of the human body, chrysoeriol has been detected, but not quantified in, several different foods, such as wild celeries, ryes, hard wheat, alfalfa, and triticales. This could make chrysoeriol a potential biomarker for the consumption of these foods. 4,5,7-trihydroxy-3-methoxyflavone is the 3-O-methyl derivative of luteolin. It has a role as an antineoplastic agent, an antioxidant and a metabolite. It is a trihydroxyflavone and a monomethoxyflavone. It is functionally related to a luteolin. It is a conjugate acid of a 4,5-dihydroxy-3-methoxyflavon-7-olate(1-). Chrysoeriol is a natural product found in Haplophyllum ramosissimum, Myoporum tenuifolium, and other organisms with data available. See also: Acai (part of); Acai fruit pulp (part of). Widespread flavone. Chrysoeriol is found in many foods, some of which are peanut, german camomile, tarragon, and alfalfa. The 3-O-methyl derivative of luteolin. Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1]. Chrysoeriol, a natural flavonoid extracted from the tropical plant Coronopus didymus, exhibits potent antioxidant activity. Chrysoeriol shows significant inhibition of lipid peroxidation[1].

D-Citronellol

C10H20O (156.1514)

Citronellol is formally classified as alkylalcohol although it is biochemically a monoterpenoid as it is synthesized from isoprene units. Citronellol is a neutral compound. It is a naturally occurring organic compound found in cannabis plants (PMID:6991645 ). Citronellol occurs in many essential oils as either ‚Äì or + enantiomers. -Citronellol is found in the oils of rose (18-55\\\\\\%) and Pelargonium geraniums while + citronellol is found in citronella oils extracted from the leaves and stems of Cymbopogon nardus or citronella grass. Citronellol has a citrus, floral, and geranium taste with a floral¬†leathery¬†waxy¬†rose¬†citrus odor ( Ref:DOI ). It is used in perfumery to add scents to soaps and incense. It is an insect repellent that repels mosquitos at short distances (PMID:2862274 ). Citronellol is found in highest concentrations in gingers, sweet basils, and winter savories and in lower concentrations in highbush blueberries, bilberries, and cardamoms. Citronellol has also been detected in blackcurrants, fennels, evergreen blackberries, herbs and spices, and nutmegs making citronellol a potential biomarker for the consumption of these foods. Citronellol has promising pharmacological activities (PMID:30453001 ) against human lung cancer (PMID:31280209 ), against induced rat breast cancer (PMID:31313341 ), has antifungal activity against Candida species (PMID:32150884 ) and has anti-hypertensive properties (PMID:26872991 ). (R)-(+)-citronellol is a citronellol that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7 (the 3R-enantiomer). It is an enantiomer of a (S)-(-)-citronellol. D-Citronellol is a natural product found in Azadirachta indica, Saxifraga stolonifera, and other organisms with data available. See also: beta-CITRONELLOL, (R)-; GERANIOL (component of); beta-CITRONELLOL, (R)-; GERANIOL; LINALOOL, (+/-)- (component of) ... View More ... Constituent of black cumin (Nigella sativa) seeds. A common constituent of plant oils, especies in the Rutaceae. D-Citronellol is found in herbs and spices. (R)-Citronellol (D-Citronellol) is an alcoholic monoterpene found in geranium essential oil. (R)-Citronellol inhibits degranulation of mast cells and does not affect caffeine bitterness perception. (R)-Citronellol can be used in decorative cosmetics, toiletries as well as in non-cosmetic products[1][2][3]. (R)-Citronellol (D-Citronellol) is an alcoholic monoterpene found in geranium essential oil. (R)-Citronellol inhibits degranulation of mast cells and does not affect caffeine bitterness perception. (R)-Citronellol can be used in decorative cosmetics, toiletries as well as in non-cosmetic products[1][2][3]. Citronellol ((±)-Citronellol) is a monoterpene Pelargonium graveolens. Citronellol ((±)-Citronellol) induces necroptosis of cancer cell via up-regulating TNF-α, RIP1/RIP3 activities, down-regulating caspase-3/caspase-8 activities and increasing ROS (reactive oxygen species) accumulation[1]. Citronellol ((±)-Citronellol) is a monoterpene Pelargonium graveolens. Citronellol ((±)-Citronellol) induces necroptosis of cancer cell via up-regulating TNF-α, RIP1/RIP3 activities, down-regulating caspase-3/caspase-8 activities and increasing ROS (reactive oxygen species) accumulation[1].

Polylimonene

C10H16 (136.1252)

Dipentene appears as a colorless liquid with an odor of lemon. Flash point 113 °F. Density about 7.2 lb /gal and insoluble in water. Hence floats on water. Vapors heavier than air. Used as a solvent for rosin, waxes, rubber; as a dispersing agent for oils, resins, paints, lacquers, varnishes, and in floor waxes and furniture polishes. Limonene is a monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively. It has a role as a human metabolite. It is a cycloalkene and a p-menthadiene. Limonene is a natural product found in Teucrium montanum, Xylopia aromatica, and other organisms with data available. Limonene, (+/-)- is a racemic mixture of limonene, a natural cyclic monoterpene and major component of the oil extracted from citrus rind with chemo-preventive and antitumor activities. The metabolites of DL-limonene, perillic acid, dihydroperillic acid, uroterpenol and limonene 1,2-diol are suggested to inhibit tumor growth through inhibition of p21-dependent signaling, induce apoptosis via the induction of the transforming growth factor beta-signaling pathway, inhibit post-translational modification of signal transduction proteins, result in G1 cell cycle arrest as well as cause differential expression of cell cycle- and apoptosis-related genes. Limonene is a metabolite found in or produced by Saccharomyces cerevisiae. A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA). See also: Cannabis sativa subsp. indica top (part of); Larrea tridentata whole (part of). Constituent of many essential oils. (±)-Limonene is found in many foods, some of which are common oregano, nutmeg, herbs and spices, and summer savory. Dipentene is found in carrot. Dipentene is a constituent of many essential oils

(-)-beta-Pinene

C10H16 (136.1252)

(-)-beta-pinene is the (1S,5S)-enantiomer of beta-pinene. It is an enantiomer of a (+)-beta-pinene. (-)-beta-Pinene is a natural product found in Curcuma amada, Molopospermum peloponnesiacum, and other organisms with data available. Flavouring ingredient. (-)-beta-Pinene is found in many foods, some of which are almond, hyssop, sweet bay, and common sage. (-)-beta-Pinene is found in almond. (-)-beta-Pinene is a flavouring ingredient. The (1S,5S)-enantiomer of beta-pinene. β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity[1][2]. β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity[1][2].

5-Isopropyl-2-methylphenol

C10H14O (150.1045)

5-Isopropyl-2-methylphenol, also known as 2-hydroxy-p-cymene or 2-p-cymenol, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. 5-Isopropyl-2-methylphenol is a very hydrophobic molecule, practically insoluble in water, but fairly soluble in organic solvents. Thus, 5-Isopropyl-2-methylphenol is considered to be an isoprenoid lipid molecule. Thymol is found in the essential oil of thyme and in the essential oils of several different plants. It can be extracted from Thymus vulgaris (common thyme), Ajwain and various other kinds of plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the culinary herb thyme, also produced from T. vulgaris. Thymol has also been identified as a volatile compound found in cannabis samples obtained from police seizures (PMID:26657499 ). Carvacrol is a phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1). It has a role as a volatile oil component, a flavouring agent, an antimicrobial agent, an agrochemical and a TRPA1 channel agonist. It is a member of phenols, a p-menthane monoterpenoid and a botanical anti-fungal agent. It derives from a hydride of a p-cymene. Carvacrol is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available. Carvacrol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Oregano Leaf Oil (part of). A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1). Constituent of many essential oils. Especies found in the Labiatae. Thyme oil (=70\\\\%) and Origanum oil (=80\\\\%) are rich sources. Flavouring ingredient COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Carvacrol is a monoterpenoid phenol isolated from Thymus mongolicus Ronn., with antioxidant, anti-inflammatory and anticancer properties. Carvacrol causes cell cycle arrest in G0/G1, downregulates Notch-1, and Jagged-1, and induces apoptosis[1]. Carvacrol is a monoterpenoid phenol isolated from Thymus mongolicus Ronn., with antioxidant, anti-inflammatory and anticancer properties. Carvacrol causes cell cycle arrest in G0/G1, downregulates Notch-1, and Jagged-1, and induces apoptosis[1].

beta-Myrcene

C10H16 (136.1252)

7-Methyl-3-methylene-1,6-octadiene, also known as beta-Myrcene or myrcene is an acyclic monoterpene. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids. beta-Myrcene is a significant component of the essential oil of several plants, including allspice, bay, cannabis, hops, houttuynia, lemon grass, mango, myrcia, verbena, west indian bay tree, and cardamom. It is also the main component of wild thyme, the leaves of which contain up to 40\\\\% by weight of myrcene. Industrially, it is produced mainly semi-synthetically from myrcia, from which it gets its name. Myrcene has been detected as a volatile component in cannabis plant samples (PMID:26657499 ) and its essential oils (PMID:6991645 ). beta-Myrcene is the most abundant monoterpene in Cannabis and it has analgesic, anti-inflammatory, antibiotic, and antimutagenic activities. beta-Myrcene is a flavouring agent and it is used in the perfumery industry. It has a pleasant odor but is rarely used directly. It is a key intermediate in the production of several fragrances such as menthol, citral, citronellol, citronellal, geraniol, nerol, and linalool. Myrcene, [liquid] appears as a yellow oily liquid with a pleasant odor. Flash point below 200 °F. Insoluble in water and less dense than water. Beta-myrcene is a monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively. It has a role as a plant metabolite, an anti-inflammatory agent, an anabolic agent, a fragrance, a flavouring agent and a volatile oil component. Myrcene is a natural product found in Teucrium montanum, Xylopia aromatica, and other organisms with data available. 7-Methyl-3-methylene-1,6-octadiene is found in allspice. 7-Methyl-3-methylene-1,6-octadiene is found in many essential oils, e.g. hop oil. 7-Methyl-3-methylene-1,6-octadiene is a flavouring agent. Myrcene is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Caraway Oil (part of); Mandarin oil (part of); Juniper Berry Oil (part of) ... View More ... A monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively. Found in many essential oils, e.g. hop oil. Flavouring agent Myrcene (β-Myrcene), an aromatic volatile compound, suppresses TNFα-induced NF-κB activity. Myrcene has anti-invasive effect[1][2]. Myrcene (β-Myrcene), an aromatic volatile compound, suppresses TNFα-induced NF-κB activity. Myrcene has anti-invasive effect[1][2].

(2S,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol

C10H18O (154.1358)

Borneol appears as a white colored lump-solid with a sharp camphor-like odor. Burns readily. Slightly denser than water and insoluble in water. Used to make perfumes. Borneol is a bornane monoterpenoid that is 1,7,7-trimethylbicyclo[2.2.1]heptane substituted by a hydroxy group at position 2. It has a role as a volatile oil component and a metabolite. Isoborneol is a natural product found in Xylopia sericea, Eupatorium capillifolium, and other organisms with data available. Both Borneol and Isoborneol and their acetates and formates are used as flavouring agents. 2-Bornanol is found in turmeric. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2]. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2].

Pulegone

C10H16O (152.1201)

A p-menthane monoterpenoid that is cyclohexan-1-one substituted by a methyl group at position 5 and a propan-2-ylidene group at position 2. Occurs in oils of Mentha subspecies, Hedeoma pulegioides and many other essential oils. Fragrance and flavour ingredient. (R)-p-Menth-4(8)-en-3-one is found in many foods, some of which are blackcurrant, pepper (c. frutescens), spearmint, and red bell pepper. Pulegone, the major chemical constituent of Nepeta catariaessential oil which is an aromatic herb, is one of avian repellents[1]. The molecular target for the repellent action of Pulegone in avian species is nociceptive TRP ankyrin 1 (TRPA1). Pulegone stimulates both TRPM8 and TRPA1 channel in chicken sensory neurons and suppresses the former but not the latter at high concentrations[2]. Pulegone, the major chemical constituent of Nepeta catariaessential oil which is an aromatic herb, is one of avian repellents[1]. The molecular target for the repellent action of Pulegone in avian species is nociceptive TRP ankyrin 1 (TRPA1). Pulegone stimulates both TRPM8 and TRPA1 channel in chicken sensory neurons and suppresses the former but not the latter at high concentrations[2].

(-)-Menthone

C10H18O (154.1358)

(-)-menthone, also known as P-menthan-3-one or (2s,5r)-2-isopropyl-5-methylcyclohexanone, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (-)-menthone is considered to be an isoprenoid lipid molecule (-)-menthone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (-)-menthone is a fresh, green, and minty tasting compound and can be found in a number of food items such as lemon, kai-lan, babassu palm, and linden, which makes (-)-menthone a potential biomarker for the consumption of these food products (-)-menthone exists in all eukaryotes, ranging from yeast to humans. (-)-Menthone, also known as (1R,4S)-menthone or L-menthone, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. (-)-Menthone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, (-)-menthone is considered to be an isoprenoid lipid molecule. (-)-menthone is a menthone that is cyclohexanone substituted by a methyl and an isopropyl group at positions 5 and 2 respectively (the 2S,5R-stereoisomer). It is an enantiomer of a (+)-menthone. Menthone is a natural product found in Xylopia aromatica, Hedeoma multiflora, and other organisms with data available. Menthone is a metabolite found in or produced by Saccharomyces cerevisiae. A menthone that is cyclohexanone substituted by a methyl and an isopropyl group at positions 5 and 2 respectively (the 2S,5R-stereoisomer). (-)-Menthone is a monoterpene component of the essential oil of maturing peppermint. (+)-Neomenthyl-β-d-glucoside is a metabolite of (-)-Menthone[1].Mortality of two biological forms of Anopheles stephensi(larvae) exposed to about 45 ppm (-)-Menthone is 27.67\\\\\\% and 94.92\\\\\\%. [2] (-)-Menthone is a monoterpene component of the essential oil of maturing peppermint. (+)-Neomenthyl-β-d-glucoside is a metabolite of (-)-Menthone[1].Mortality of two biological forms of Anopheles stephensi(larvae) exposed to about 45 ppm (-)-Menthone is 27.67\\\\\% and 94.92\\\\\%. [2] (-)-Menthone is a monoterpene component of the essential oil of maturing peppermint. (+)-Neomenthyl-β-d-glucoside is a metabolite of (-)-Menthone[1].Mortality of two biological forms of Anopheles stephensi(larvae) exposed to about 45 ppm (-)-Menthone is 27.67\\\\% and 94.92\\\\%. [2] (-)-Menthone is a monoterpene component of the essential oil of maturing peppermint. (+)-Neomenthyl-β-d-glucoside is a metabolite of (-)-Menthone[1].Mortality of two biological forms of Anopheles stephensi(larvae) exposed to about 45 ppm (-)-Menthone is 27.67\\\% and 94.92\\\%. [2] Menthone, a monoterpene extracted from plants and Mentha oil with strong antioxidant properties. Menthone is a main volatile component of the essential oil, and has anti-Inflammatory properties in Schistosoma mansoni Infection[1][2]. Menthone, a monoterpene extracted from plants and Mentha oil with strong antioxidant properties. Menthone is a main volatile component of the essential oil, and has anti-Inflammatory properties in Schistosoma mansoni Infection[1][2].

Amyrin

C30H50O (426.3861)

Beta-amyrin is a pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. It has a role as a plant metabolite and an Aspergillus metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an oleanane. beta-Amyrin is a natural product found in Ficus pertusa, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Centaurium erythraea whole (part of). A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1]. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1].

Phytol

C20H40O (296.3079)

Phytol, also known as trans-phytol or 3,7,11,15-tetramethylhexadec-2-en-1-ol, is a member of the class of compounds known as acyclic diterpenoids. Acyclic diterpenoids are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, phytol is considered to be an isoprenoid lipid molecule. Phytol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Phytol can be found in a number of food items such as salmonberry, rose hip, malus (crab apple), and black raspberry, which makes phytol a potential biomarker for the consumption of these food products. Phytol can be found primarily in human fibroblasts tissue. Phytol is an acyclic diterpene alcohol that can be used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1. In ruminants, the gut fermentation of ingested plant materials liberates phytol, a constituent of chlorophyll, which is then converted to phytanic acid and stored in fats. In shark liver it yields pristane . Phytol is a diterpenoid that is hexadec-2-en-1-ol substituted by methyl groups at positions 3, 7, 11 and 15. It has a role as a plant metabolite, a schistosomicide drug and an algal metabolite. It is a diterpenoid and a long-chain primary fatty alcohol. Phytol is a natural product found in Elodea canadensis, Wendlandia formosana, and other organisms with data available. Phytol is an acyclic diterpene alcohol and a constituent of chlorophyll. Phytol is commonly used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1. Furthermore, phytol also was shown to modulate transcription in cells via transcription factors PPAR-alpha and retinoid X receptor (RXR). Acyclic diterpene used in making synthetic forms of vitamin E and vitamin K1. Phytol is a natural linear diterpene alcohol which is used in the preparation of vitamins E and K1. It is also a decomposition product of chlorophyll. It is an oily liquid that is nearly insoluble in water, but soluble in most organic solvents. -- Wikipedia. A diterpenoid that is hexadec-2-en-1-ol substituted by methyl groups at positions 3, 7, 11 and 15. C1907 - Drug, Natural Product > C28269 - Phytochemical Acquisition and generation of the data is financially supported in part by CREST/JST. Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1]. Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1].

Caryophyllene alpha-oxide

C15H24O (220.1827)

Caryophyllene oxide is an epoxide. It has a role as a metabolite. Caryophyllene oxide is a natural product found in Xylopia emarginata, Eupatorium altissimum, and other organisms with data available. See also: Cannabis sativa subsp. indica top (part of). Caryophyllene alpha-oxide is a minor produced of epoxidn. of KGV69-V. Minor production of epoxidn. of KGV69-V Caryophyllene oxide, isolated from from Hymenaea courbaril, possesses analgesic and anti-inflammatory activity[1]. Caryophyllene oxide, isolated from from Hymenaea courbaril, possesses analgesic and anti-inflammatory activity[1].

Thymol

C10H14O (150.1045)

Thymol is a phenol that is a natural monoterpene derivative of cymene. It has a role as a volatile oil component. It is a member of phenols and a monoterpenoid. It derives from a hydride of a p-cymene. A phenol obtained from thyme oil or other volatile oils. It is used as a stabilizer in pharmaceutic preparations. It has been used for its antiseptic, antibacterial, and antifungal actions, and was formerly used as a vermifuge. (Dorland, 28th ed) Thymol is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available. A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent. See also: Paeonia lactiflora root (part of); Elymus repens root (part of); Eucalyptol; thymol (component of) ... View More ... Thymol is a phenol obtained from thyme oil or other volatile oils. It is used as a stabilizer in pharmaceutic preparations. It has been used for its antiseptic, antibacterial, and antifungal actions, and was formerly used as a vermifuge. Thymol is a monoterpene phenol derivative of cymene, C10H13OH, isomeric with carvacrol, found in oil of thyme, and extracted as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. It is also called "hydroxy cymene". In a 1994 report released by five top cigarette companies, thymol is one of the 599 additives to cigarettes. Its use or purpose, however, is unknown, like most cigarette additives. Found in many essential oils. Especies found in the Labiatae. Rich sources are thyme oil, seed oil of Ptychotis ajowan and oils of horsemint (Monarda punctata) and Ocimum subspecies Flavouring ingredient C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000890 - Anti-Infective Agents > D000935 - Antifungal Agents A phenol that is a natural monoterpene derivative of cymene. Thymol is the main monoterpene phenol occurring in essential oils isolated from plants belonging to the Lamiaceae family, and other plants such as those belonging to the Verbenaceae, Scrophulariaceae, Ranunculaceae and Apiaceae families. Thymol has antioxidant, anti-inflammatory, antibacterial and antifungal effects[1]. Thymol is the main monoterpene phenol occurring in essential oils isolated from plants belonging to the Lamiaceae family, and other plants such as those belonging to the Verbenaceae, Scrophulariaceae, Ranunculaceae and Apiaceae families. Thymol has antioxidant, anti-inflammatory, antibacterial and antifungal effects[1].

beta-Geraniol

C10H18O (154.1358)

Geraniol is a colorless to pale yellow oily liquid with a sweet rose odor. (NTP, 1992) Geraniol is a monoterpenoid consisting of two prenyl units linked head-to-tail and functionalised with a hydroxy group at its tail end. It has a role as a fragrance, an allergen, a volatile oil component and a plant metabolite. It is a monoterpenoid, a primary alcohol and a 3,7-dimethylocta-2,6-dien-1-ol. Geraniol is a monoterpene that is found within many essential oils of fruits, vegetables, and herbs including rose oil, citronella, lemongrass, lavender, and other aromatic plants. It is emitted from the flowers of many species of plant and is commonly used by the food, fragrance, and cosmetic industry. Geraniol has demonstrated a wide spectrum of pharmacological activities including antimicrobial, anti-inflammatory, antioxidant, anti-cancer, and neuroprotective to name a few. Interestingly, geraniol has also been shown to sensitize tumour cells to commonly used chemotherapies including [DB00544] and [DB01248] and represents a promising cancer chemopreventive agent. Due to its anticancer effects, geraniol has been found to be effective against a broad range of cancers including breast, lung, colon, prostate, pancreatic, skin, liver, kidney and oral cancers. These pharmacologic effects are clinically important as geraniol is classified as generally-recognized-as-safe (GRAS) by the Flavor and Extract Manufacturers Association (FEMA) and the Food and Drug Administration (FDA) of the United States. Sensitivity to geraniol may be identified with a clinical patch test. Geraniol is a Standardized Chemical Allergen. The physiologic effect of geraniol is by means of Increased Histamine Release, and Cell-mediated Immunity. Geraniol is a natural product found in Xylopia sericea, Eupatorium cannabinum, and other organisms with data available. beta-Geraniol is found in almond. beta-Geraniol is found in free state and as esters in many essential oils including geranium oil. Most prolific natural source is palmarosa oil. beta-Geraniol is a flavouring agent. Geraniol is a monoterpenoid and an alcohol. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type). It also occurs in small quantities in geranium, lemon, and many other essential oils. It has a rose-like odor and is commonly used in perfumes. It is used in flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. It is the isomer of nerol. (Wikipedia) beta-Geraniol belongs to the family of Monoterpenes. These are compounds contaning a chain of two isoprene units. Geraniol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Coriander Oil (part of); Java citronella oil (part of). beta-Geraniol, also known as (E)-nerol, the isomer of nerol (or geranyl alcohol, is a monoterpenoid alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. beta-Geraniol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. beta-Geraniol has a sweet, citrus, and floral taste. beta-Geraniol is found in highest concentrations in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. beta-Geraniol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. This could make beta-geraniol a potential biomarker for the consumption of these foods. It is found in as an alcohol and as its ester in many essential oils including geranium oil. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type) and occurs in small quantities in geranium, lemon, and many other essential oils. Geraniol is a monoterpenoid and an alcohol found in cannabis plants (PMID:6991645 ). Because it has a rose-like odor, it is commonly used in perfumes. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403). Found in free state and as esters in many essential oils including geranium oil. Most prolific natural source is palmarosa oil. Flavouring agent A monoterpenoid consisting of two prenyl units linked head-to-tail and functionalised with a hydroxy group at its tail end. C26170 - Protective Agent > C275 - Antioxidant Geraniol, an olefinic terpene, was found to inhibit growth of Candida albicans and Saccharomyces cerevisiae strains[1]. Geraniol, an olefinic terpene, was found to inhibit growth of Candida albicans and Saccharomyces cerevisiae strains[1]. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2]. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2]. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2].

Geraniol

C10H18O (154.1358)

Geraniol, also known as beta-Geraniol, (E)-nerol (the isomer of nerol) or geranyl alcohol, is a monoterpenoid alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. In plants, the biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. beta-Geraniol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. beta-Geraniol has a sweet, citrus, and floral taste. beta-Geraniol is found in highest concentrations in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. beta-Geraniol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. It is found as an alcohol and as its ester in many essential oils including geranium oil. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type) and occurs in small quantities in geranium, lemon, and many other essential oils. Because it has a rose-like odor, it is commonly used in perfumes. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. An alternate application has been found in the use of insect repellents or deterrants. Though it may repel mosquitoes, flies, lice, cockroaches, ants, and ticks, it is also produced by the scent glands of honey bees to help them mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403). Extensive testing by Dr. Jerry Butler at the University of Florida has shown geraniol to be one of natures most effective insect repellents (PMID:20836800). Nerol is the (2Z)-stereoisomer of 3,7-dimethylocta-2,6-dien-1-ol. It has been isolated from the essential oils from plants like lemon grass. It has a role as a volatile oil component, a plant metabolite and a fragrance. Nerol is a natural product found in Eupatorium cannabinum, Vitis rotundifolia, and other organisms with data available. Nerol is a metabolite found in or produced by Saccharomyces cerevisiae. Constituent of many essential oils including neroli and bergamot oils. In essential oils it is a minor component always accompanied by geraniol. Flavouring agent The (2Z)-stereoisomer of 3,7-dimethylocta-2,6-dien-1-ol. It has been isolated from the essential oils from plants like lemon grass. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2]. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2]. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2].

Cuminyl alcohol

C10H14O (150.1045)

Cuminol or Cuminyl alcohol, also known as p-cumin-7-ol or 4-Isopropylbenzyl alcohol, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Cuminol is an extremely weak basic (essentially neutral) compound (based on its pKa). Cuminol is an alcohol derivative of p-Cymene. It exists as a clear, colorless liquid that is poorly soluble in water. Cuminol can be used as a food additive or as a cosmetic fragrance. It has a cumin, caraway or spicy, herbal aroma and a similar spicy, herbal or peppery taste. Cuminol is found naturally in a number of plants, spices and foods including cumin seed and cumin oils, caraway eucalyptus oils, thyme, sunflowers, tuermeric, guava fruit and other spices and essential oils. Cumin, a widely used spice, is known to have anti-diabetic properties and two of its phytochemicals: cuminol and cuminaldehyde appear to be among the most active components. Cuminol is a potent insulinotrophic molecule that can enhance insulin secretion by up to 4-fold (in rat islet cells) (PMID:23507295 ). It also exhibits strong beta-cell protective action (PMID:23507295 ). 4-isopropylbenzyl alcohol is a member of the class of benzyl alcohols in which the hydrogen at position 4 on the phenyl ring of benzyl alcohol has been replaced by an isopropyl group. It has a role as a fragrance, an insect repellent, a volatile oil component, a plant metabolite and a xenobiotic metabolite. It is a p-menthane monoterpenoid and a member of benzyl alcohols. It is functionally related to a p-cymene. 4-Isopropylbenzyl alcohol is a natural product found in Xylopia aromatica, Curcuma amada, and other organisms with data available. Flavouring ingredient. Isolated from oils of Cuminum cyminum (cumin). Cuminyl alcohol is found in many foods, some of which are sweet bay, sunflower, cumin, and herbs and spices. A member of the class of benzyl alcohols in which the hydrogen at position 4 on the phenyl ring of benzyl alcohol has been replaced by an isopropyl group. 4-Isopropylbenzyl alcohol is a chemical composition of the essential oils from the leaves and flowers of Camellia nitidissima. C. nitidissima possess multiple biological activities including antioxidant activity, anticancer activity, and cytotoxicity as well as inhibiting the formation of advanced glycation end-products[1]. 4-Isopropylbenzyl alcohol is a chemical composition of the essential oils from the leaves and flowers of Camellia nitidissima. C. nitidissima possess multiple biological activities including antioxidant activity, anticancer activity, and cytotoxicity as well as inhibiting the formation of advanced glycation end-products[1].

Geranyl acetate

C12H20O2 (196.1463)

Geranyl acetate is a clear colorless liquid with an odor of lavender. (NTP, 1992) Geranyl acetate is a monoterpenoid that is the acetate ester derivative of geraniol. It has a role as a plant metabolite. It is an acetate ester and a monoterpenoid. It is functionally related to a geraniol. Geranyl acetate is a natural product found in Nepeta nepetella, Xylopia sericea, and other organisms with data available. See also: Lemon oil, cold pressed (part of); Coriander Oil (part of); Java citronella oil (part of). Neryl acetate is found in cardamom. Neryl acetate is found in citrus, kumquat and pummelo peel oils, ginger, cardamon, clary sage, myrtle leaf and myrtle berries. Neryl acetate is a flavouring agent A monoterpenoid that is the acetate ester derivative of geraniol. Geranyl acetate, an acyclic monoterpene ester derived from geraniol, is widely used in the cosmetics industry due to its pleasant scent[1]. Geranyl acetate can induces cell apoptosis[2]. Geranyl acetate, an acyclic monoterpene ester derived from geraniol, is widely used in the cosmetics industry due to its pleasant scent[1]. Geranyl acetate can induces cell apoptosis[2].

Epi-alpha-amyrin

C30H50O (426.3861)

Alpha-amyrin is a pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an ursane. alpha-Amyrin is a natural product found in Ficus septica, Ficus virens, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Eupatorium perfoliatum whole (part of) ... View More ... Carissol is found in beverages. Carissol is a constituent of Carissa carandas (karanda). Constituent of Carissa carandas (karanda). Carissol is found in beverages and fruits.

beta-Phellandrene

C10H16 (136.1252)

beta-Phellandrene is found in allspice. beta-Phellandrene is widely distributed in essential oils (Angelica, Eucalyptus, Lavandula, Mentha, Pinus species). beta-Phellandrene is a flavour ingredient.Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (Wikipedia Beta-phellandrene is one of a pair of phellandrene cyclic monoterpene double-bond isomers in which one double bond is exocyclic (cf. alpha-phellandrene, where both of them are endoocyclic). It has a role as a plant metabolite. beta-Phellandrene is a natural product found in Xylopia aromatica, Dacrydium nausoriense, and other organisms with data available. See also: Cannabis sativa subsp. indica top (part of). One of a pair of phellandrene cyclic monoterpene double-bond isomers in which one double bond is exocyclic (cf. alpha-phellandrene, where both of them are endoocyclic). Widely distributed in essential oils (Angelica, Eucalyptus, Lavandula, Mentha, Pinus subspecies). Flavour ingredient β-Phellandrene is obtained from Carum petroselinum. β-Phellandrene can be used to essential oil additives[1]. β-Phellandrene is obtained from Carum petroselinum. β-Phellandrene can be used to essential oil additives[1].

gamma-Cadinene

C15H24 (204.1878)

(-)-gamma-cadinene is a member of the cadinene family of sesquiterpenes in which the isopropyl group is cis to the hydrogen at the adjacent bridgehead carbon (the 1R,4aS,8aS enantiomer). It has a role as a metabolite. It is a cadinene, a member of octahydronaphthalenes and a gamma-cadinene. It is an enantiomer of a (+)-gamma-cadinene. (-)-gamma-Cadinene is a natural product found in Xylopia sericea, Chromolaena odorata, and other organisms with data available. A member of the cadinene family of sesquiterpenes in which the isopropyl group is cis to the hydrogen at the adjacent bridgehead carbon (the 1R,4aS,8aS enantiomer). gamma-Cadinene is found in allspice. gamma-Cadinene is a constituent of citronella oil.

2-Hydroxycinnamic acid

C9H8O3 (164.0473)

2-coumaric acid, also known as o-coumaric acid, is a monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 2-coumarate. It is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acids: o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. 2-Hydroxycinnamic acid belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 2-Hydroxycinnamic acid exists in all living organisms, ranging from bacteria to humans. 2-Hydroxycinnamic acid has been found in a few different foods, such as corns, hard wheats, and olives and in a lower concentration in pomegranates, american cranberries, and peanuts. 2-Hydroxycinnamic acid has also been detected, but not quantified in several different foods, such as carrots, soy beans, ryes, rye bread, and turmerics. Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. o-Coumaric acid is found in many foods, some of which are common wheat, date, bilberry, and corn. 2-coumaric acid is a monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 2-coumarate. 2-Hydroxycinnamic acid is a natural product found in Mikania glomerata, Coffea arabica, and other organisms with data available. See also: Ipomoea aquatica leaf (part of). The trans-isomer of 2-coumaric acid. o-Coumaric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=583-17-5 (retrieved 2024-07-01) (CAS RN: 583-17-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

p-Menth-1-en-4-ol

C10H18O (154.1358)

p-Menth-1-en-4-ol, also known as terpinen-4-ol, 1-para-menthen-4-ol or p-Menth-1-en-4-ol or 4-carvomenthenol, is an isomer of terpineol. It belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. ±-Terpinene-4-ol is a hydrophobic, largely neutral molecule that is essentially insoluble in water. It has a peppery, spicy, musty, citrus odor and a cooling woody or spicy taste. ±-Terpinene-4-ol is widely used as a flavoring agent and as a masking agent in cosmetics. ±-Terpinene-4-ol is a natural product that can be found in a number of plants, such as allspice, anise, apple, basil, cardamom, cinnamon and Melaleuca alternifolia (also called tea tree) and is the main bioactive component of tea tree oil (PMID 22083482 ). ±-Terpinene-4-ol is also one of the monoterpenes found in cannabis plants (PMID:6991645 ). Terpinen-4-ol is a potent bactericidal agent that also possess antifungal properties. In particular, it has shown in vitro activity against Staphylococcus aureus and C. albicans (PMID:27275783 ). It has also been shown that combining this natural substance and conventional drugs may help treat resistant yeast and bacterial infections. Several studies have suggested that terpinen-4-ol induces antitumor effects by selectively causing necrotic cell death and cell-cycle arrest in melanoma cell lines, or by triggering caspase-dependent apoptosis in human melanoma cells (PMID:27275783 ). 4-terpineol is a terpineol that is 1-menthene carrying a hydroxy substituent at position 4. It has a role as a plant metabolite, an antibacterial agent, an antioxidant, an anti-inflammatory agent, an antiparasitic agent, an antineoplastic agent, an apoptosis inducer and a volatile oil component. It is a terpineol and a tertiary alcohol. Terpinen-4-ol is under investigation in clinical trial NCT01647217 (Demodex Blepharitis Treatment Study). 4-Carvomenthenol is a natural product found in Nepeta nepetella, Teucrium montanum, and other organisms with data available. Terpinen-4-ol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Lavender Oil (part of); Juniper Berry Oil (part of); Peumus boldus leaf (part of). Flavouring ingredient. p-Menth-1-en-4-ol is found in many foods, some of which are star anise, spearmint, sweet basil, and black elderberry. A terpineol that is 1-menthene carrying a hydroxy substituent at position 4. Terpinen-4-ol (4-Carvomenthenol), a naturally occurring monoterpene, is the main bioactive component of tea-tree oil. Terpinen-4-ol suppresses inflammatory mediator production by activated human monocytes. Terpinen-4-ol significantly enhances the effect of several chemotherapeutic and biological agents[1][2][3]. Terpinen-4-ol (4-Carvomenthenol), a naturally occurring monoterpene, is the main bioactive component of tea-tree oil. Terpinen-4-ol suppresses inflammatory mediator production by activated human monocytes. Terpinen-4-ol significantly enhances the effect of several chemotherapeutic and biological agents[1][2][3].

alpha-Terpinene

C10H16 (136.1252)

Alpha-Terpinene is one of four isomers of terpinene (the other three being beta terpinene, gamma terpenine, and delta terpinine or terpimolene) that differ in the position of carbon-carbon double bonds. Alpha-Terpinene belongs to the class of organic compounds known as menthane monoterpenes. These are monoterpenes with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. alpha-Terpinene is a naturally occurring monoterpene found in allspice, cardamom, and marjoram. alpha-Terpinene is a constituent of many essential oils with oil from Litsea ceylanica being is a major source (20\\\\%) of it. alpha-Terpinene has been found in Citrus, Eucalyptus and Juniperus species, and cannabis plants (PMID:6991645 ). ±-Terpinene is a flavouring agent and is produced industrially by acid-catalyzed rearrangement of ±-pinene. It has perfume and flavoring properties but is mainly used to confer a pleasant odor to industrial fluids. Alpha-terpinene is one of three isomeric monoterpenes differing in the positions of their two double bonds (beta- and gamma-terpinene being the others). In alpha-terpinene the double bonds are at the 1- and 3-positions of the p-menthane skeleton. It has a role as a volatile oil component and a plant metabolite. It is a monoterpene and a cyclohexadiene. alpha-Terpinene is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available. One of three isomeric monoterpenes differing in the positions of their two double bonds (beta- and gamma-terpinene being the others). In alpha-terpinene the double bonds are at the 1- and 3-positions of the p-menthane skeleton. Alpha-terpinene, also known as 1-isopropyl-4-methyl-1,3-cyclohexadiene or 1-methyl-4-(1-methylethyl)-1,3-cyclohexadiene, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, alpha-terpinene is considered to be an isoprenoid lipid molecule. Alpha-terpinene is a camphoraceous, citrus, and herbal tasting compound and can be found in a number of food items such as summer savory, cabbage, pot marjoram, and wild celery, which makes alpha-terpinene a potential biomarker for the consumption of these food products. Alpha-terpinene can be found primarily in saliva. Alpha-terpinene exists in all eukaryotes, ranging from yeast to humans. α-Terpinene (Terpilene) is a monoterpene found in the essential oils of a large variety of foods and aromatic plants such as Mentha piperita. α-Terpinene is active against Trypanosoma evansi and has the potential for trypanosomosis treatment. α-Terpinene has antioxidant and antifungal properties[1][2][3][4]. α-Terpinene (Terpilene) is a monoterpene found in the essential oils of a large variety of foods and aromatic plants such as Mentha piperita. α-Terpinene is active against Trypanosoma evansi and has the potential for trypanosomosis treatment. α-Terpinene has antioxidant and antifungal properties[1][2][3][4].

gamma-Terpinene

C10H16 (136.1252)

Gamma-terpinene is one of three isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton. It has a role as an antioxidant, a plant metabolite, a volatile oil component and a human xenobiotic metabolite. It is a monoterpene and a cyclohexadiene. gamma-Terpinene is a natural product found in Teucrium montanum, Xylopia aromatica, and other organisms with data available. The terpinenes are three isomeric hydrocarbons that are classified as terpenes. Gamma-terpinene is one these three isomeric hydrocarbons. It is natural and has been isolated from a variety of plant sources (Wikipedia). It is a major component of essential oils made from Citrus Fruits and has strong antioxidant activity. It has a lemon odor and widely used in food, flavours, soaps, cosmetics, pharmaceutical, tabacco, confectionery and perfume industries (http://www.gyanflavoursexport.com). See also: Lemon oil, cold pressed (part of); Coriander Oil (part of); Mandarin oil (part of). Gamma-terpinene is one of four isomeric monoterpenes (the other three being alpha terpinene, beta terpinene and delta terpinene). It is a naturally occurring terpinene and has been isolated from a variety of plant sources. It has the highest boiling point of the four known terpinene isomers. It is a major component of essential oils made from citrus fruits and has a strong antioxidant activity. It has a lemon-like or lime-like odor and is widely used in food, flavours, soaps, cosmetics, pharmaceutical, tabacco, confectionery and perfume industries (http://www.gyanflavoursexport.com). The other isomers of gamma-terpinene, such as alpha-terpinene and delta-terpinene, have been isolated from cardamom and marjoram oils while beta terpinene appears to have no natural source. One of three isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton. Constituent of many essential oils e.g. Citrus, Eucalyptus, Mentha, Pinus subspecies Ajowan seed oil (Carum copticum) is a major source γ-Terpinene, a monoterpene, is an orally active antioxidant compound which can scavenge radicals directly. γ-Terpinene has potent antinociception activity[1]. γ-Terpinene, a monoterpene, is an orally active antioxidant compound which can scavenge radicals directly. γ-Terpinene has potent antinociception activity[1].

(+)-alpha-Pinene

C10H16 (136.1252)

alpha-Pinene (CAS: 80-56-8) is an organic compound of the terpene class and is one of two isomers of pinene. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary (Rosmarinus officinalis). Both enantiomers are known in nature. 1S,5S- or (-)-alpha-pinene is more common in European pines, whereas the 1R,5R- or (+)-alpha-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil (Wikipedia). alpha-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary (Rosmarinus officinalis). Both enantiomers are known in nature; 1S,5S- or (-)-alpha-pinene is more common in European pines, whereas the 1R,5R- or (+)-alpha-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil. (+)-alpha-pinene is the (+)-enantiomer of alpha-pinene. It has a role as a plant metabolite and a human metabolite. It is an enantiomer of a (-)-alpha-pinene. (+)-alpha-Pinene is a natural product found in Juniperus drupacea, Eucalyptus deglupta, and other organisms with data available. The (+)-enantiomer of alpha-pinene. (1R)-α-Pinene is a volatile monoterpene with antimicrobial activities. (1R)-α-Pinene reduces Bacillus cereus population growth, and exhibits repellent effects[1][2]. (1R)-α-Pinene is a volatile monoterpene with antimicrobial activities. (1R)-α-Pinene reduces Bacillus cereus population growth, and exhibits repellent effects[1][2].

Cuminaldehyde

C10H12O (148.0888)

Cuminaldehyde is the biologically active constituent of Cuminum cyminum seed oil. C. cyminum seed-derived materials have an inhibitory effect in vitro against rat lens aldose reductase and alpha-glucosidase. This inhibitory action cuminaldehyde suggest a potential utility as an antidiabetic therapeutic. (PMID:15796577). Cuminaldehyde is a volatile compound representative of cumin aroma present in trace amounts in the blood and milk of ewes fed with cumin seed. (PMID:8738023). The terpenoid cuminaldehyde, undergoes reduction biotransformation in mammals, but not oxidation. (PMID:2815827). Cuminaldehyde is a member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities. It has a role as an insecticide, a volatile oil component and a plant metabolite. It derives from a hydride of a cumene. 4-Isopropylbenzaldehyde is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available. See also: Paeonia lactiflora root (part of). A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities. Found in many essential oils, including eucalyptus, cumin and cassiaand is also present in grilled or roast beef and cognac. Flavouring agent Cuminaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=122-03-2 (retrieved 2024-07-11) (CAS RN: 122-03-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Cuminaldehyde is the major component of Cuminum cyminum, a natural aldehyde with inhibitory effect on alpha-synuclein fibrillation and cytotoxicity. Cuminaldehyde shows anticancer activity[1]. Cuminaldehyde is the major component of Cuminum cyminum, a natural aldehyde with inhibitory effect on alpha-synuclein fibrillation and cytotoxicity. Cuminaldehyde shows anticancer activity[1].

(+)-Camphor

C10H16O (152.1201)

Camphor, also known as (+)-camphor or (+)-bornan-2-one, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Camphor is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Within the cell, camphor is primarily located in the membrane (predicted from logP). Camphor is a waxy, flammable, white or transparent solid with a strong aroma. It is a terpenoid with the chemical formula C10H16O. It is found in many plants, such as in the wood of the camphor laurel (Cinnamomum camphora), a large evergreen tree found in Asia (particularly in Sumatra and Borneo islands, Indonesia) and also of the unrelated Kapur tree, a tall timber tree from the same region. It also occurs in some other related trees in the laurel family, notably Ocotea usambarensis and in the oil in rosemary leaves (Rosmarinus officinalis). The mint family contains 10 to 20\\\\\\\\% camphor, while camphorweed (Heterotheca) only contains some 5\\\\\\\\%. Camphor can also be synthetically produced from oil of turpentine. It is used for its scent, as an ingredient in cooking (mainly in India), as an embalming fluid, for medicinal purposes, and in religious ceremonies. A major source of camphor in Asia is camphor basil (the parent of African blue basil) (Wikipedia). (R)-camphor is the (R)- enantiomer of camphor. It is an enantiomer of a (S)-camphor. Camphor is a bicyclic monoterpene ketone found widely in plants, especially Cinnamomum camphora. It is used topically as a skin antipruritic and as an anti-infective agent. When ingested, camphor has a rapid onset of toxic effects, and camphorated oil is the product most often responsible for its toxicity. The FDA ruled that camphorated oil could not be marketed in the United States and that no product could contain a concentration higher than 11\\\\\\\\%. It appears in the list of drug products withdrawn or removed from the market for safety or effectiveness. However, camphor can be found in several nonprescription medications at lower concentrations. D-Camphor is a natural product found in Chromolaena odorata, Curcuma amada, and other organisms with data available. See also: Coriander Oil (part of). C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent C - Cardiovascular system > C01 - Cardiac therapy The (R)- enantiomer of camphor. (+)-Camphor is a food additive used medicinally as a preservative. (+)-Camphor is a food additive used medicinally as a preservative. (+)-Camphor is a food additive used medicinally as a preservative. (+)-Camphor is a food additive used medicinally as a preservative. Camphor ((±)-Camphor) is a topical anti-infective and anti-pruritic and internally as a stimulant and carminative. However, Camphor is poisonous when ingested. Antiviral, antitussive, and anticancer activities[1]. Camphor is a TRPV3 agonist[2]. Camphor ((±)-Camphor) is a topical anti-infective and anti-pruritic and internally as a stimulant and carminative. However, Camphor is poisonous when ingested. Antiviral, antitussive, and anticancer activities[1]. Camphor is a TRPV3 agonist[2].

Eugenol

C10H12O2 (164.0837)

Eugenol appears as clear colorless pale yellow or amber-colored liquid. Odor of cloves. Spicy pungent taste. (NTP, 1992) Eugenol is a phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. It is a major component of clove essential oil, and exhibits antibacterial, analgesic and antioxidant properties. It has been widely used in dentistry to treat toothache and pulpitis. It has a role as an allergen, a human blood serum metabolite, a sensitiser, a volatile oil component, a flavouring agent, an EC 1.4.3.4 (monoamine oxidase) inhibitor, a radical scavenger, an antibacterial agent, an antineoplastic agent, an apoptosis inducer, an anaesthetic, an analgesic, a voltage-gated sodium channel blocker, a NF-kappaB inhibitor and an anti-inflammatory agent. It is a phenylpropanoid, a monomethoxybenzene, a member of phenols and an alkenylbenzene. It is functionally related to a guaiacol. Eugenol is a naturally occurring phenolic molecule found in several plants such as cinnamon, clove, and bay leaves. It has been used as a topical antiseptic as a counter-irritant and in dental preparations with zinc oxide for root canal sealing and pain control. Although not currently available in any FDA-approved products (including OTC), eugenol has been found to have anti-inflammatory, neuroprotective, antipyretic, antioxidant, antifungal and analgesic properties. Its exact mechanism of action is unknown, however, it has been shown to interfere with action potential conduction. There are a number of unapproved OTC products available containing eugenol that advertise its use for the treatment of toothache. Eugenol is a Standardized Chemical Allergen. The physiologic effect of eugenol is by means of Increased Histamine Release, and Cell-mediated Immunity. Eugenol, also called clove oil, is an aromatic oil extracted from cloves that is used widely as a flavoring for foods and teas and as an herbal oil used topically to treat toothache and more rarely to be taken orally to treat gastrointestinal and respiratory complaints. Eugenol in therapeutic doses has not been implicated in causing serum enzyme elevations or clinically apparent liver injury, but ingestions of high doses, as with an overdose, can cause severe liver injury. Eugenol is a natural product found in Dahlia sherffii, Elettaria cardamomum, and other organisms with data available. Eugenol is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. Eugenol is a member of the allylbenzene class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like odor. Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia). 4-Allyl-2-methoxyphenol is a metabolite found in or produced by Saccharomyces cerevisiae. A cinnamate derivative of the shikimate pathway found in CLOVE OIL and other PLANTS. See also: Cinnamon (part of); Clove Oil (part of); Cinnamon Leaf Oil (part of) ... View More ... Eugenol is an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like aroma. Eugenol is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia). Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic. It is a key ingredient in Indonesian kretek (clove) cigarettes. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from phenol or from lignin. It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study. Eugenol has a very widespread occurrence in essential oils. Major component of clove oil. Also found in citrus and thyme oils. It is found in foods such as apple, apricot, banana and cherry fruits. Eugenol or 4-allyl-2-methoxyphenol is classified as a phenylpropanoid, formally derived from guaiacol, with an allyl chain positioned para to the hydroxy group. It is soluble in water, alcohol, chloroform, ether and oils. Eugenol is a neutral compound. It is biosynthesized from tyrosine. Eugenol is widely distributed in plants. It is a clear to pale yellow oily liquid extracted from clove oil, nutmeg, cinnamon, basil and bay leaf. It has a pleasant, spicy, clove-like odor with a spicy pungent taste. Eugenol is found in highest concentrations in cloves, allspices, and carrots and in lower concentrations in walnuts, ceylon cinnamons, and wild carrots. Eugenol has also been detected in shea tree, passion fruits, winged beans, fireweeds, and gingers, making it a potential biomarker for the consumption of these foods. Eugenol is used in perfumeries, flavorings and essential oils. It was first used for the manufacture of vanillin (https://doi.org/10.1021/ed054p776), though most vanillin is now produced from petrochemicals or from by-products of paper manufacture. Eugenol is hepatotoxic, meaning it may cause damage to the liver, if consumed in high doses. Eugenol has local antiseptic and anaesthetic properties (PMID:15089054 ; PMID:935250 ) and acts as positive allosteric modulators of the GABA-A receptor. It has high antioxidant, anti-proliferative, and anti-inflammatory activities with potential roles in alleviating and preventing cancer and inflammatory reactions (PMID:27771920 ). A phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. It is a major component of clove essential oil, and exhibits antibacterial, analgesic and antioxidant properties. It has been widely used in dentistry to treat toothache and pulpitis. C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent D000890 - Anti-Infective Agents D012997 - Solvents [Raw Data] CB226_Eugenol_pos_10eV_CB000079.txt [Raw Data] CB226_Eugenol_pos_20eV_CB000079.txt [Raw Data] CB226_Eugenol_pos_40eV_CB000079.txt [Raw Data] CB226_Eugenol_pos_50eV_CB000079.txt [Raw Data] CB226_Eugenol_pos_30eV_CB000079.txt Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation. Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation.

17a-Ethynylestradiol

C20H24O2 (296.1776)

Ethinyl estradiol. A semisynthetic alkylated estradiol with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in oral contraceptives. -- Pubchem; estradiol (17-beta estradiol) (also oestradiol) is a sex hormone. Labelled the "female" hormone but also present in males it represents the major estrogen in humans. Critical for sexual functioning, estradiol also supports bone growth. -- Wikipedia; One of the fascinating twists to mammalian sexual differentiation is that estradiol is one of the two active metabolites of testosterone in males (the other being dihydrotestosterone). estradiol cannot be transferred readily from the circulation into the brain. Since fetuses of both sexes are exposed to similarly high levels of maternal estradiol, it can play little role in prenatal sexual differentiation. However, testosterone enters the central nervous system more freely and significant amounts are aromatized to estradiol within the brain of most male mammals, including humans. There is now much evidence that the programming of adult male sexual behavior in "lower mammals," (such as mounting rather than lordosis behavior), is largely dependent on estradiol produced in the central nervous system during prenatal life and early infancy from testosterone. We do not yet know whether this process plays a minimal or significant part in human sexual behaviors. -- Wikipedia; A synthetic form of estradiol, called ethinyl estradiol is a major component of hormonal contraceptive devices. Combined oral contraceptives contain ethinyl estradiol and a progestin, which both contribute to the inhibition of GnRH, LH, and FSH. The inhibition of these hormones accounts for the ability of combined oral contraceptives or birth control pills to prevent ovulation and thus prevent pregnancy. Other types of hormonal birth control contain only progestins and no ethinyl estradiol. -- Wikipedia. A synthetic form of estradiol, called ethinyl estradiol is a major component of hormonal contraceptive devices. 17alpha-ethynylestradiol is found in many foods, some of which are common walnut, ginkgo nuts, allspice, and papaya. G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CA - Natural and semisynthetic estrogens, plain L - Antineoplastic and immunomodulating agents > L02 - Endocrine therapy > L02A - Hormones and related agents > L02AA - Estrogens D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Ethinylestradiol (Ethynyl estradiol) is a biologically active estrogen. Ethinylestradiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. Ethinylestradiol (Ethynyl estradiol) is a biologically active estrogen. Ethinylestradiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

Isobutyric acid

C4H8O2 (88.0524)

Isobutyric acid is a carboxylic or short chain fatty acid with characteristic sweat-like smell. Small amount of isobutyrate is generated via microbial (gut) metabolism. Small amounts may also be found in certain foods or fermented beverages. There is anosmia (genetic inability to smell) for the odor of isobutyric acid with a frequency of about 2.5\\%. (OMIM 207000). Isobutyric acid is slightly soluble in water but much more soluble in ethanol, ether and organic solvents. Isobutyric acid can affect people if breathed in and may be absorbed through the skin. Contact can irritate and burn the skin and eyes. Breathing Isobutyric acid can irritate the nose, throat and lungs causing coughing, wheezing and/or shortness of breath. Present in apple, morello cherry, guava fruit, wine grapes, pineapple, crispbread, other breads, cheeses, wines, scallop and several essential oils, e.g. Roman chamomile. Acid and simple esters used as flavouring agents KEIO_ID I012

(3S,6E)-Nerolidol

C15H26O (222.1984)

(3S,6E)-Nerolidol, also known as nerolidol or peruviol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (3S,6E)-nerolidol is considered to be an isoprenoid lipid molecule. (3S,6E)-Nerolidol is an isomer of nerolidol, a naturally occurring sesquiterpene found in the essential oils of many types of plants and flowers. An isomer of nerolidol, a naturally occurring sesquiterpene found in the essential oils of many types of plants and flowers [Wikipedia] Nerolidol is a natural membrane-active sesquiterpene, with antitumor, antibacterial, antifungal and antiparasitic activity[1]. Nerolidol is a natural membrane-active sesquiterpene, with antitumor, antibacterial, antifungal and antiparasitic activity[1].

Delphinidin

[C15H11O7]+ (303.0505)

Delphinidin, also known as delphinidin chloride (CAS: 528-53-0), belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton. Thus, delphinidin is considered to be a flavonoid lipid molecule. Delphinidin is found, on average, in the highest concentration within a few different foods, such as bilberries, cowpea, and blackcurrants, and in a lower concentration in common beans, common pea, and wheats. Delphinidin has also been detected, but not quantified in, several different foods, such as Brussel sprouts, fruits, horseradish tree, pepper (C. pubescens), and macadamia nuts. This could make delphinidin a potential biomarker for the consumption of these foods. Delphinidin is an anthocyanin and a primary plant pigment. Delphinidin gives blue hues to flowers like violas and delphiniums. It also gives the blue-red colour of the grape that produces Cabernet Sauvignon, and can be found in cranberries (Wikipedia). BioTransformer predicts that delphinidin is a product of 5,7-dihydroxy-3-{oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium metabolism via a glycoside-hydrolysis reaction occurring in human gut microbiota and catalyzed by an EC.3.2.1.X enzyme (PMID: 30612223). Widespread anthocyanidin found especies in blueberries, raspberries and red table wine. Glycosides also widespread. Delphinidin is found in many foods, some of which are macadamia nut (m. tetraphylla), oval-leaf huckleberry, napa cabbage, and sunburst squash (pattypan squash). 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-1-benzopyrylium. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=13270-61-6 (retrieved 2024-09-18) (CAS RN: 13270-61-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Vicenin 2

C27H30O15 (594.1585)

Constituent of lemons (Citrus limon). Vicenin 2 is found in many foods, some of which are common salsify, fenugreek, sweet orange, and cucumber. Vicenin 2 is found in citrus. Vicenin 2 is a constituent of lemons (Citrus limon) Vicenin 2 is an angiotensin-converting enzyme (ACE) inhibitor (IC50=43.83 μM) from the aerial parts of Desmodium styracifolium[1]. Vicenin 2 is an angiotensin-converting enzyme (ACE) inhibitor (IC50=43.83 μM) from the aerial parts of Desmodium styracifolium[1].

alpha-Cadinol

C15H26O (222.1984)

alpha-Cadinol is found in cloves. alpha-Cadinol is a constituent of Juniperus communis (juniper)

(±)-Citronellyl acetate

C12H22O2 (198.162)

(±)-Citronellyl acetate, also known as b-citronellol acetic acid or cephrol acetate, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. (±)-Citronellol acetate is a monoterpenoid that is the acetate ester of citronellol. It has been isolated from Citrus hystrix. (±)-Citronellyl acetate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Flavouring ingredient. Constituent of citronella oil, orange juice, lemon juice and peel, grapefruit peel, swangi (Citrus hystrix), ginger, tarragon, myrtle leaf, West Indian lemongrass oil and beer. (±)-Citronellyl acetate is found in many foods, some of which are herbs and spices, carrot, wild carrot, and blackcurrant. Citronellyl acetate is a monoterpene product of the secondary metabolism of plants, with antinociceptive activity. Citronellyl acetate exhibits pro-apoptotic activity in human hepatoma cells. Citronellyl acetate shows fungicidal, larvicidal, bactericidal and repelling/insecticidal effects[1]. Citronellyl acetate is a monoterpene product of the secondary metabolism of plants, with antinociceptive activity. Citronellyl acetate exhibits pro-apoptotic activity in human hepatoma cells. Citronellyl acetate shows fungicidal, larvicidal, bactericidal and repelling/insecticidal effects[1].

malvidin

[C17H15O7]+ (331.0818)

alpha-Copaene

C15H24 (204.1878)

alpha-Copaene, also known as aglaiene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. alpha-Copaene is possibly neutral. alpha-Copaene is a spice and woody tasting compound that can be found in several food items such as lime, mandarin orange (clementine, tangerine), safflower, and summer savoury, which makes alpha-copaene a potential biomarker for the consumption of these food products. alpha-Copaene can be found in feces and saliva. Alpha-copaene, also known as copaene, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Alpha-copaene is a spice and woody tasting compound and can be found in a number of food items such as lime, mandarin orange (clementine, tangerine), safflower, and summer savory, which makes alpha-copaene a potential biomarker for the consumption of these food products. Alpha-copaene can be found primarily in feces and saliva. 8-Isopropyl-1,3-dimethyltricyclo(4.4.0.02,7)dec-3-ene is a natural product found in Pinus sylvestris var. hamata, Asarum gusk, and other organisms with data available.

Camphene

C10H16 (136.1252)

Camphene, also known as 2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane or 2,2-dimethyl-3-methylenenorbornane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Camphene is nearly insoluble in water but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It exists as a flammable, white solid that has a minty, citrus, eucalyptus odor. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and in food additives for flavouring. In the mid-19th century it was used as a fuel for lamps, but this was limited by its explosiveness. Camphene exists in all eukaryotes, ranging from yeast to plants to humans. Camphene can be found in a number of food items such as dill, carrots, caraway, hyssop, lemon, orange, nutmeg seed, parsley, sage, thyme, turmeric and fennel, which makes camphene a potential biomarker for the consumption of these food products. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian. Camphene is one of several monoterpenes that are found in cannabis plants (PMID:6991645 ). Camphene, also known as 2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane or 2,2-dimethyl-3-methylenenorbornane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Camphene is a camphor, fir needle, and herbal tasting compound and can be found in a number of food items such as cardamom, yellow bell pepper, common thyme, and coriander, which makes camphene a potential biomarker for the consumption of these food products. Camphene can be found primarily in feces and saliva. Camphene exists in all eukaryotes, ranging from yeast to humans. Camphene is a bicyclic monoterpene. It is nearly insoluble in water, but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and as a food additive for flavoring. Its mid-19th century use as a fuel for lamps was limited by its explosiveness .

(-)-trans-Carveol

C10H16O (152.1201)

Carveol is a natural terpenoid alcohol that is a constituent of spearmint oil. It has an odor and flavor that resemble those of spearmint and caraway. Consequently, it is used as a fragrance in cosmetics and as a flavor additive in the food industry. Constituent of Valencia orange essence oil. Flavouring ingredient Carveol is an endogenous metabolite. Carveol is an endogenous metabolite.

Eucalyptol

C10H18O (154.1358)

Eucalyptol is an organic compound that is a colourless liquid. It is a cyclic ether and a monoterpene. Eucalyptol is a natural constituent of a number of aromatic plants and their essential oil fraction. Eucalyptol was given GRAS (Generally Recognized As Safe) status by the Flavor and Extract Manufacturers Association FEMA, 1965 and is approved by the Food and Drug Administration for food use. 1,8-Dihydroxy-10-carboxy-p-menthane, 2-hydroxy-cineole, and 3-hydroxy-cineole are the main metabolites of eucalyptol. Toxicological data available on eucalyptol are rather limited. Following accidental exposure, death was reported in two cases after ingestion of 3.5-5 mL of essential eucalyptus oil, but a number of recoveries have also been described for much higher amounts of oil. In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes. It is usually added to improve the flavour (PMID:12048025). R - Respiratory system > R05 - Cough and cold preparations > R05C - Expectorants, excl. combinations with cough suppressants > R05CA - Expectorants COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials C78273 - Agent Affecting Respiratory System > C74536 - Mucolytic Agent D019141 - Respiratory System Agents > D000996 - Antitussive Agents D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents D010575 - Pesticides > D007302 - Insect Repellents D003358 - Cosmetics > D009067 - Mouthwashes D001697 - Biomedical and Dental Materials D002491 - Central Nervous System Agents D000890 - Anti-Infective Agents D020011 - Protective Agents D016573 - Agrochemicals D012997 - Solvents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

(R)-1-Octen-3-ol

C8H16O (128.1201)

Isolated from a number of essential oils, e.g. lavender, leek, mint and mushrooms. Food odorant responsible for typical mushroom odour. Flavouring ingredient. (R)-1-Octen-3-ol is found in mushrooms, onion-family vegetables, and herbs and spices. (R)-1-Octen-3-ol, also known as 1-vinylhexanol or 3-hydroxy-1-octene, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms Oct-1-en-3-ol, a fatty acid fragrant, is a self-stimulating oxylipin messenger. Oct-1-en-3-ol serves as a signaling molecule in plant cellular responses, plant-herbivore interactions, and plant-plant interactions. Oct-1-en-3-ol causes dopamine neuron degeneration through disruption of dopamine handling[1][2]. Oct-1-en-3-ol, a fatty acid fragrant, is a self-stimulating oxylipin messenger. Oct-1-en-3-ol serves as a signaling molecule in plant cellular responses, plant-herbivore interactions, and plant-plant interactions. Oct-1-en-3-ol causes dopamine neuron degeneration through disruption of dopamine handling[1][2].

2-Phenylethanol

C8H10O (122.0732)

2-Phenylethanol, also known as benzeneethanol or benzyl carbinol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 2-Phenylethanol exists in all living species, ranging from bacteria to humans. 2-Phenylethanol is a bitter, floral, and honey tasting compound. 2-Phenylethanol is found, on average, in the highest concentration within a few different foods, such as red wines, black walnuts, and white wines and in a lower concentration in grape wines, sweet basils, and peppermints. 2-Phenylethanol has also been detected, but not quantified, in several different foods, such as asparagus, allspices, fruits, horned melons, and lemons. 2-Phenylethanol, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, pervasive developmental disorder not otherwise specified, and autism. 2-phenylethanol has also been linked to the inborn metabolic disorder celiac disease. A primary alcohol that is ethanol substituted by a phenyl group at position 2. Flavouring ingredient. Component of ylang-ylang oil. 2-Phenylethanol is found in many foods, some of which are hickory nut, arrowhead, allspice, and nance. C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000890 - Anti-Infective Agents D010592 - Pharmaceutic Aids D004202 - Disinfectants 2-Phenylethanol (Phenethyl alcohol), extracted from rose, carnation, hyacinth, Aleppo pine, orange blossom and other organisms, is a colourless liquid. It has a pleasant floral odor and also an autoantibiotic produced by the fungus Candida albicans[1]. It is used as an additive in cigarettes and also used as a preservative in soaps due to its stability in basic conditions. 2-Phenylethanol (Phenethyl alcohol), extracted from rose, carnation, hyacinth, Aleppo pine, orange blossom and other organisms, is a colourless liquid. It has a pleasant floral odor and also an autoantibiotic produced by the fungus Candida albicans[1]. It is used as an additive in cigarettes and also used as a preservative in soaps due to its stability in basic conditions.

p-Cymene

C10H14 (134.1095)

Cymene, or p-cymene also known as p-cymol or isopropyltoluene, is a naturally occurring aromatic organic compound. It is classified as a hydrocarbon related to a monoterpene. Its structure consists of a benzene ring para-substituted with a methyl group and an isopropyl group. It is insoluble in water, but miscible with ethanol and ether. Cymene is a constituent of a number of essential oils, most commonly the oil of cumin and thyme. There are two less common geometric isomers. o-Cymene, in which the alkyl groups are ortho-substituted, and m-cymene, in which they are meta-substituted. p-Cymene is the only natural isomer. Cymene is a common ligand for ruthenium. V. widely distributed in plant oils e.g. terpentine and citrus oils and many others. It is used in flavour industries. 1-Isopropyl-4-methylbenzene is found in many foods, some of which are green bell pepper, lemon balm, saffron, and sweet basil.

Terpinolene

C10H16 (136.1252)

Terpinolene (TPO), also known as alpha-terpinolene or isoterpinene, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, terpinolene is considered to be an isoprenoid lipid molecule. Terpinolene is a very hydrophobic monoterpenoid, practically insoluble in water, and relatively neutral. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes in plants is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Terpinolene is one of the constituents of turpentine and an isomer of terpinene. It appears colourless to pale yellow liquid. Alpha-terpinolene has been identified as an abundant monoterpene in the essential oil of Cannabis sativa plants (PMID:6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. Although common in cannabis cultivars, terpinolene is typically found in relatively low amounts. On the other hand, the concentration of terpinolene can be has high as 30\\% of the essential oil. It is thought that terpinolene offers a mildly sedative effect and can reduce anxiety (PMID:28826544 ). In particular, terpinolene is a central nervous system depressant that has been shown to induce drowsiness (PMID:23339024 ). Terpinolene has been demonstrated to prevent LDL oxidation and is of potential interest in the treatment of atherogenesis and coronary artery disease (PMID:28826544 ). Terpinolene exhibits antifungal and larvicidal properties (PMID:28826544 ). Terpinolene is also an effective anti-microbial agent, particularly against E coli and Staphylococcus bacteria (PMID:16402540 ). Terpinolene is also employed as a fragrence ingredient in lotions, insect repellents (similar to other terpenes), perfumes, and soaps. Terpinolene is also a constituent of many other essential oils e. g. Citrus, Mentha, Juniperus, Myristica species. Parsnip oil (Pastinaca sativa) in particular, is a major source (40-70\\%). Terpinolene is a sweet, citrus, and fresh tasting compound. It produces a floral, woody or herbal aroma reminiscent of pine needles. In addition to being found in various plant essential oils, terpinolene is found in a few different foods and spices, such as allspice, apples, sage, rosemary, parsnips, nutmegs, and wild carrots and in a lower concentration in sweet bay, star anises, turmerics, apricots, cumins, evergreen blackberries, red bell peppers, and caraway. Constituent of many essential oils e.g. Citrus, Mentha, Juniperus, Myristica subspecies Parsnip oil (Pastinaca sativa) is a major source (40-70\\%). Flavouring ingredient. Terpinolene is found in many foods, some of which are coriander, ceylon cinnamon, pine nut, and caraway.

beta-Cadinene

C15H24 (204.1878)

beta-Cadinene is found in common oregano. beta-Cadinene is a constituent of Pinus caribaea. Mixed cadinene isomers, with b-cadinene usually predominating, occur in several essential oils, especially ylang-ylang, citronella and cade oil from Juniper species Cadinene isomers are used as a flavouring agent and/or flavour modifier.

Chromium

Cr (51.9405)

D018977 - Micronutrients > D014131 - Trace Elements

(+)-1(10),4-Cadinadiene

C15H24 (204.1878)

Constituent of the essential oils of ylang-ylang, citronella, cubebs, and sweetflag. (+)-1(10),4-Cadinadiene is found in many foods, some of which are common pea, asparagus, sweet potato, and dill. (+)-1(10),4-Cadinadiene is found in allspice. (+)-1(10),4-Cadinadiene is a constituent of the essential oils of ylang-ylang, citronella, cubebs, and sweetflag

beta-Caryophyllene

C15H24 (204.1878)

beta-Caryophyllene, also known as caryophyllene or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils including that of Syzygium aromaticum (cloves), Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. beta-Caryophyllene is notable for having both a cyclobutane ring and a trans-double bond in a nine-membered ring, both rarities in nature (Wikipedia). beta-Caryophyllene is a sweet and dry tasting compound that can be found in a number of food items such as allspice, fig, pot marjoram, and roman camomile, which makes beta-caryophyllene a potential biomarker for the consumption of these food products. beta-Caryophyllene can be found in feces and saliva. (-)-Caryophyllene. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=87-44-5 (retrieved 2024-08-07) (CAS RN: 87-44-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.

alpha-Cedrene

C15H24 (204.1878)

Alpha-cedrene, also known as (-)-α-cedrene or beta-cedrene, is a member of the class of compounds known as cedrane and isocedrane sesquiterpenoids. Cedrane and isocedrane sesquiterpenoids are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. Thus, alpha-cedrene is considered to be an isoprenoid lipid molecule. Alpha-cedrene is a sweet, cedar, and fresh tasting compound and can be found in a number of food items such as tarragon, peppermint, wild celery, and common sage, which makes alpha-cedrene a potential biomarker for the consumption of these food products. Alpha-cedrene can be found primarily in urine. alpha-Cedrene alpha-Cedrene is one of the two isomers of cedrene. Cedrene is a sesquiterpene found in the essential oil of cedar. There are two isomers of cedrene, (-)-alpha-cedrene and (+)-beta-cedrene, which differ in the position of a double bond (Wikipedia) (-)-Cedrene (α-cedrene) is a sesquiterpene constituent of cedarwood oils, with anti-leukemic, antimicrobial and anti-obesity activities[1]. (-)-Cedrene (α-cedrene) is a sesquiterpene constituent of cedarwood oils, with anti-leukemic, antimicrobial and anti-obesity activities[1]. (-)-Cedrene (α-cedrene) is a sesquiterpene constituent of cedarwood oils, with anti-leukemic, antimicrobial and anti-obesity activities[1]. (-)-Cedrene (α-cedrene) is a sesquiterpene constituent of cedarwood oils, with anti-leukemic, antimicrobial and anti-obesity activities[1].

alpha-Cubebene

C15H24 (204.1878)

alpha-Cubebene is found in cloves. alpha-Cubebene is a constituent of oil of cubeb pepper (Piper cubeba).

(-)-Bornyl acetate

C12H20O2 (196.1463)

(-)-Bornyl acetate is isolated from Blumea balsamifera, Jasonia sp., Salvia fruticosa, carrot, rosemary, sage and lavender oil. (-)-Bornyl acetate is a flavouring agent [CCD]. Isolated from Blumea balsamifera, Jasonia species, Salvia fruticosa, carrot, rosemary, sage and lavender oil. Flavouring agent [CCD] (-)-Bornyl acetate (L-(-)-Bornyl acetate), isolated from hyssop oil, is a less active enantiomer of (+)-Bornyl acetate. (-)-Bornyl acetate possesses antifungal activity[1]. (-)-Bornyl acetate (L-(-)-Bornyl acetate), isolated from hyssop oil, is a less active enantiomer of (+)-Bornyl acetate. (-)-Bornyl acetate possesses antifungal activity[1]. (-)-Bornyl acetate (L-(-)-Bornyl acetate), isolated from hyssop oil, is a less active enantiomer of (+)-Bornyl acetate. (-)-Bornyl acetate possesses antifungal activity[1]. (-)-Bornyl acetate (L-(-)-Bornyl acetate), isolated from hyssop oil, is a less active enantiomer of (+)-Bornyl acetate. (-)-Bornyl acetate possesses antifungal activity[1].

(+)-alpha-Carene

C10H16 (136.1252)

(+)-alpha-Carene is found in herbs and spices. (+)-alpha-Carene is widespread plant product, found especially in turpentine oils (from Pinus species) and oil of galbanu Isolated from root oil of Kaempferia galanga. (-)-alpha-Carene is found in many foods, some of which are pummelo, cumin, herbs and spices, and sweet orange.

fenchone

C10H16O (152.1201)

A carbobicyclic compound that is fenchane in which the hydrogens at position 2 are replaced by an oxo group. It is a component of essential oil from fennel (Foeniculum vulgare). Fenchone is a natural organic compound classified as a monoterpene and a ketone. It is a colorless oily liquid. It has a structure and an odor similar to camphor. Fenchone is a constituent of absinthe and the essential oil of fennel. Fenchone is used as a flavor in foods and in perfumery. Only 2 stereoisomers are possible: D-fenchone (enantiomer 1S,4R is dextrogyre (+)) and L-fenchone (enantiomer 1R,4S is levogyre (-)). Due to the small size of the cycle, the 2 other diastereoisomers (1S4S and 1R4R) are not possible. [Wikipedia]. Fenchone is found in many foods, some of which are ceylon cinnamon, sweet basil, saffron, and dill. (-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1]. (-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1]. (-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1]. (-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1].

trans-Ocimene

C10H16 (136.1252)

trans-Ocimene is found in allspice. trans-Ocimene is a constituent of the pheromones of Anastrepha suspensa, Euploea tulliolus koxinga, and Labidus species (CCD). Ocimene refers to several isomeric hydrocarbons. The ocimenes are monoterpenes found within a variety of plants and fruits. alpha-Ocimene and the two beta-ocimenes differ in the position of the isolated double bond: it is terminal in the alpha-isomer. alpha-Ocimene is 3,7-dimethyl-1,3,7-octatriene. beta-Ocimene is 3,7-dimethyl-1,3,6-octatriene. beta-Ocimene exists in two stereoisomeric forms, cis and trans, with respect to the central double bond. The ocimenes are often found naturally as mixtures of the various forms. The mixture (as well as the pure compounds) is an oil with a pleasant odour and it is used in perfumery. Constituent of the pheromones of Anastrepha suspensa, Euploea tulliolus koxinga and Labidus subspecies [CCD]

(-)-Pinocarvone

C10H14O (150.1045)

Pinocarvone, also known as (1)-2(10)-pinen-3-one or pina-2(10)-ene-3-one, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, pinocarvone is considered to be an isoprenoid lipid molecule. Pinocarvone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Pinocarvone is a minty tasting compound found in hyssop, spearmint, and sweet bay, which makes pinocarvone a potential biomarker for the consumption of these food products. (-)-Pinocarvone is isolated from oil of Eucalyptus globulus (Tasmanian blue gum

alpha-Terpineol

C10H18O (154.1358)

alpha-Terpineol (CAS: 98-55-5) is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers of terpineol, alpha-, beta-, and gamma-terpineol, with the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. Terpineol has a pleasant odour similar to lilac and is a common ingredient in perfumes, cosmetics, and flavours. alpha-Terpineol is occasionally found as a volatile component in urine. It is a water-soluble component of Melaleuca alternifolia Cheel, the tea tree oil (TTO). alpha-Terpineol is a likely mediator of the in vitro and in vivo activity of the TTO as an agent that could control C. albicans vaginal infections. Purified alpha-terpineol can suppress pro-inflammatory mediator production by activated human monocytes. alpha-Terpineol is able to impair the growth of human M14 melanoma cells and appear to be more effective on their resistant variants, which express high levels of P-glycoprotein in the plasma membrane, overcoming resistance to caspase-dependent apoptosis exerted by P-glycoprotein-positive tumour cells (PMID:5556886, 17083732, 11131302, 15009716). Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. (R)-alpha-Terpineol is found in many foods, some of which are mentha (mint), sweet marjoram, lovage, and cardamom. α-Terpineol is isolated from Eucalyptus globulus Labill, exhibits strong antimicrobial activity against periodontopathic and cariogenic bacteria[1]. α-Terpineol possesses antifungal activity against T. mentagrophytes, and the activity might lead to irreversible cellular disruption[2]. α-Terpineol is isolated from Eucalyptus globulus Labill, exhibits strong antimicrobial activity against periodontopathic and cariogenic bacteria[1]. α-Terpineol possesses antifungal activity against T. mentagrophytes, and the activity might lead to irreversible cellular disruption[2].

2-Pinen-10-ol

C10H16O (152.1201)

2-Pinen-10-ol is found in citrus. 2-Pinen-10-ol is a flavouring ingredient. 2-Pinen-10-ol is present in mandarin peel oil, raspberry, blackberry, strawberry, ginger, hop oil, black tea, peppermint oil, pepper (Piper nigrum), myrtle leaf or berry, summer savoury (Satureja hortensis) and other foodstuffs (±)-Myrtenol is a flavouring ingredient. It is found in mandarin peel oil, raspberry, blackberry, strawberry, ginger, hop oil, black tea, peppermint oil, pepper (Piper nigrum), myrtle leaf or berry, summer savoury (Satureja hortensis) and other foods.

Myrtenal

C10H14O (150.1045)

Occurs in orange, lemon, spearmint, pepper, thyme, juniper, calamus, ginger, myrtle, lemon balm, calabash, nutmeg, parsley seed and other plant oils. Myrtenal is found in many foods, some of which are peppermint, fruits, wild celery, and sweet bay. Myrtenal is found in cardamom. Myrtenal occurs in orange, lemon, spearmint, pepper, thyme, juniper, calamus, ginger, myrtle, lemon balm, calabash, nutmeg, parsley seed and other plant oils.

Pinocarveol

C10H16O (152.1201)

Flavouring ingredient. Pinocarveol is found in many foods, some of which are spearmint, wild celery, hyssop, and sweet bay. Pinocarveol is found in hyssop. Pinocarveol is a flavouring ingredien

Xanthomicrol

C18H16O7 (344.0896)

Isolated from Citrus sudachi, Mentha piperita, Sideritis subspecies and Thymus subspecies Xanthomicrol is found in many foods, some of which are citrus, herbs and spices, sweet basil, and winter savory. low.

o-Ethyltoluene

C9H12 (120.0939)

o-Ethyltoluene belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group. o-Ethyltoluene is possibly neutral. These are compounds containing a benzene ring which bears a methane group.

Germacrene D

C15H24 (204.1878)

Germacrene d, also known as germacrene d, (s-(e,e))-isomer, is a member of the class of compounds known as germacrane sesquiterpenoids. Germacrane sesquiterpenoids are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Germacrene d can be found in a number of food items such as peppermint, roman camomile, hyssop, and common walnut, which makes germacrene d a potential biomarker for the consumption of these food products.

beta-Bisabolene

C15H24 (204.1878)

S-beta-Bisabolene is found in anise. S-beta-Bisabolene is a constituent of the essential oils of bergamot, lemon and wild carrot Flavouring ingredient used singly or as mixed isomers. Component of FEMA 3331. See also 2,7,10-Bisabolatriene JHG85-W β-Bisabolene is a?sesquiterpene isolated from?opoponax (Commiphora guidotti). β-Bisabolene, an anti-cancer agent, can be used for the study of breast cancer[1]. β-Bisabolene is a?sesquiterpene isolated from?opoponax (Commiphora guidotti). β-Bisabolene, an anti-cancer agent, can be used for the study of breast cancer[1].

beta-Terpineol

C10H18O (154.1358)

beta-Terpineol is found in cardamom. beta-Terpineol is a flavouring ingredient.Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. (Wikipedia). Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. cis-beta-Terpineol is found in caraway, rosemary, and common sage.

Gurjunene-alpha

C15H24 (204.1878)

Alpha-Gurjunene or (-)-Alpha-Gurjunene, belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpenoid as it synthesized via isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-Gurjunene is a neutral, hydrophobic molecule that is insoluble in water. It exists as a colorless clear Liquid and has a woody, balsamic odor. It is used as a perfuming agent. Alpha-gurjunene is found in many plants, essential oils and foods including allspice, bay leaf, carrot seeds, eucalyptus, guava, parsley, black papper, sage and tea tree oil.

(+)-Ledene

C15H24 (204.1878)

(+)-Ledene belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.

1,7,7-Trimethyltricyclo[2.2.1.02,6]heptane

C10H16 (136.1252)

1,7,7-Trimethyltricyclo[2.2.1.02,6]heptane is found in caraway. 1,7,7-Trimethyltricyclo[2.2.1.02,6]heptane is found in essential oils, e.g. Juniperus communis (Juniper), Ferula galbaniflua (galbanum) and Picea species. Found in essential oils, e.g. Juniperus communis (Juniper), Ferula galbaniflua (galbanum) and Picea subspecies

(+)-Limonene

C10H16 (136.1252)

(+)-Limonene, also known as d-limonene, is a naturally occurring monoterpene which is the major component in orange oil. Currently, (+)-limonene is widely used as a flavour and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration (21 CFR 182.60 in the Code of Federal Regulations, U.S.A.). Recently, however, (+)-limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Furthermore, chronic exposure to (+)-limonene causes a significant incidence of renal tubular tumours exclusively in male rats. Although (+)-limonene is not carcinogenic in female rats or male and female mice given much higher dosages, the male rat-specific nephrocarcinogenicity of (+)-limonene may raise some concern regarding the safety of (+)-limonene for human consumption. A considerable body of scientific data has indicated that the renal toxicity of (+)-limonene results from the accumulation of a protein, alpha 2u-globulin, in male rat kidney proximal tubule lysosomes. This protein is synthesized exclusively by adult male rats. Other species, including humans, synthesize proteins that share significant homology with alpha 2u-globulin. However, none of these proteins, including the mouse equivalent of alpha 2u-globulin, can produce this toxicity, indicating a unique specificity for alpha 2u-globulin. With chronic exposure to (+)-limonene, the hyaline droplet nephropathy progresses and the kidney shows tubular cell necrosis, granular cast formation at the corticomedullary junction, and compensatory cell proliferation. Both (+)-limonene and cis-d-limonene-1,2-oxide (the major metabolite involved in this toxicity) are negative in vitro mutagenicity screens. Therefore, the toxicity-related renal cell proliferation is believed to be integrally involved in the carcinogenicity of (+)-limonene as persistent elevations in renal cell proliferation may increase fixation of spontaneously altered DNA or serve to promote spontaneously initiated cells. The scientific data demonstrates that the tumorigenic activity of (+)-limonene in male rats is not relevant to humans. The three major lines of evidence supporting the human safety of (+)-limonene are (1) the male rat specificity of the nephrotoxicity and carcinogenicity; (2) the pivotal role that alpha 2u-globulin plays in the toxicity, as evidenced by the complete lack of toxicity in other species despite the presence of structurally similar proteins; and (3) the lack of genotoxicity of both (+)-limonene and d-limonene-1,2-oxide, supporting the concept of a nongenotoxic mechanism, namely, sustained renal cell proliferation (PMID:2024047). (4r)-limonene, also known as (+)-4-isopropenyl-1-methylcyclohexene or (R)-1-methyl-4-(1-methylethenyl)cyclohexene, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (4r)-limonene is considered to be an isoprenoid lipid molecule (4r)-limonene can be found in sweet marjoram, which makes (4r)-limonene a potential biomarker for the consumption of this food product (4r)-limonene can be found primarily in saliva.

(S)-Carvone

C10H14O (150.1045)

Carvone, with R and S isomers, also known as carvol or limonen-6-one, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Carvone is a neutral compound. Carvone is a naturally occurring organic compound found in many essential oils but is most abundant in the oils from caraway seeds (Carum carvi), spearmint (Mentha spicata), and dill (PMID:27427817). Carvone is occasionally found as a component of biological fluids in normal individuals. Both carvones (R, S) are used in the food and flavor industry (http//doi:10.1016/j.foodchem.2005.01.003). R-carvone is also used in air freshening products and in essential oils used in aromatherapy and alternative medicine. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841 (PMID:5556886 , 2477620 ). Carvone may help in the management of diseases (PMID:30374904) and had been considered as an adjuvant for treatment of cancer patients (PMID:30087792) and patients with epilepsy (PMID:31239862). It also has been successfully used as a biopesticide (PMID:30250476). D-carvone appears as pale yellow or colorless liquid. (NTP, 1992) (+)-carvone is a carvone having (S) configuration. It is an enantiomer of a (-)-carvone. d-Carvone is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available. See also: Caraway Oil (part of). A carvone having (S) configuration.

(+)-Menthone

C10H18O (154.1358)

(+)-Menthone is found in herbs and spices. (+)-Menthone is found in some essential oils, e.g. those of Barosma pulchellum, Mentha sachalinensi Found in some essential oils, e.g. those of Barosma pulchellum, Mentha sachalinensis

(R)-3,7-Dimethyl-1,6-octadien-3-ol

C10H18O (154.1358)

(R)-3,7-Dimethyl-1,6-octadien-3-ol is found in coriander. (R)-3,7-Dimethyl-1,6-octadien-3-ol is a constituent of many essential oils including Melissa officinalis (lemon balm), rose, neroli and lavender. (R)-3,7-Dimethyl-1,6-octadien-3-ol is a major component of oil of field mint (Mentha arvensis) Constituent of many essential oils including Melissa officinalis (lemon balm), rose, neroli and lavender. Major component of oil of field mint (Mentha arvensis). L-Linalool is found in many foods, some of which are tea, cumin, pummelo, and coriander.

Pinene

C10H16 (136.1252)

Pinene (is a bicyclic monoterpene chemical compound. There are two structural isomers of pinene found in nature: alpha-pinene and beta-pinene. As the name suggests, both forms are important constituents of pine resin; they are also found in the resins of many other conifers, as well as in non-coniferous plants. Both isomers are used by many insects in their chemical communication system.

Epimuurolene

C15H24 (204.1878)

Gamma-cadinene, also known as D-G-cadinene or gamma-cadinene, (+)-isomer, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Gamma-cadinene is a wood tasting compound and can be found in a number of food items such as hyssop, lemon balm, sweet orange, and common sage, which makes gamma-cadinene a potential biomarker for the consumption of these food products. Gamma-cadinene can be found primarily in saliva. Chemically, the cadinenes are bicyclic sesquiterpenes. The term cadinene has sometimes also been used in a broad sense to refer to any sesquiterpene with the so-called cadalane (4-isopropyl-1,6-dimethyldecahydronaphthalene) carbon skeleton. Because of the large number of known double-bond and stereochemical isomers, this class of compounds has been subdivided into four subclasses based on the relative stereochemistry at the isopropyl group and the two bridgehead carbon atoms. The name cadinene is now properly used only for the first subclass below, which includes the compounds originally isolated from cade oil. Only one enantiomer of each subclass is depicted, with the understanding that the other enantiomer bears the same subclass name .