NCBI Taxonomy: 268879

Carnosol

C20H26O4 (330.1831)

Carnosol is a naturally occurring phenolic diterpene found in rosemary (Rosemarinus officinalis, Labiatae). It has been known that an extract of rosemary leaves contains high antioxidative activity. Ninety percent of this antioxidative activity can be attributed to carnosol and carnosic acid. Carnosic acid is easily converted to carnosol by oxidation. Carnosol has multiple beneficial medicinal effects including anti-inflammatory, anti-microbial and anti-cancer activities in various disease models. Carnosol may possess important neuroprotective effects against rotenone-induced DA neuronal damage. Naturally occurring antioxidants reduce the risk of neurodegenerative diseases. In addition, carnosol and carnosic acid promoted the synthesis of nerve growth factor in glial cells. Carnosol-mediated neuroprotection in DA neurons is involved in the attenuation of caspase-3 activity, which was induced by rotenone. Furthermore, carnosol-mediated tyrosine hydroxylase (TH) increase, which is dependent on the Raf-mitogen-activated protein kinase (MEK)-extracellular signal-regulated kinase (ERK)1/2 signaling pathway, is responsible for the neuroprotection in SN4741 DA cells. (PMID: 17047462). Carnosol, a phenolic diterpene compound of the labiate herbs rosemary and sage, is an activator of the human peroxisome proliferator-activated receptor gamma (PPARgamma), a ligand activated transcription factor, belonging to the metazoan family of nuclear hormone receptors. Activation of PPARgamma increases the transcription of enzymes involved in primary metabolism, leading to lower blood levels of fatty acids and glucose. Hence, PPARgamma represents the major target for the glitazone type of drugs currently being used clinically for the treatment of type 2 diabetes. (PMID: 16858665). Bitter principle in Salvia carnosa, Salvia officinalis (sage), Salvia triloba (Greek sage) and Rosmarinus officinalis (rosemary). Nutriceutical with anticancer props. Carnosol is a diterpenoid. Carnosol is a natural product found in Podocarpus rumphii, Lepechinia salviae, and other organisms with data available.

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].

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.

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.

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].

Beta-eudesmol

C15H26O (222.1984)

Beta-eudesmol is a carbobicyclic compound that is trans-decalin substituted at positions 2, 4a, and 8 by 2-hydroxypropan-2-yl, methyl and methylidene groups, respectively (the 2R,4aR,8aS-diastereoisomer). It has a role as a volatile oil component. It is a carbobicyclic compound, a tertiary alcohol and a eudesmane sesquiterpenoid. beta-Eudesmol is a natural product found in Rhododendron calostrotum, Rhododendron lepidotum, and other organisms with data available. See also: Arctium lappa Root (part of); Cannabis sativa subsp. indica top (part of); Pterocarpus marsupium wood (part of). A carbobicyclic compound that is trans-decalin substituted at positions 2, 4a, and 8 by 2-hydroxypropan-2-yl, methyl and methylidene groups, respectively (the 2R,4aR,8aS-diastereoisomer). Beta-Eudesmol is a natural oxygenated sesquiterpene, activates hTRPA1, with an EC50 of 32.5 μM. Beta-Eudesmol increases appetite through TRPA1[1]. Beta-Eudesmol is a natural oxygenated sesquiterpene, activates hTRPA1, with an EC50 of 32.5 μM. Beta-Eudesmol increases appetite through TRPA1[1].

Carnosic_acid

C20H28O4 (332.1987)

Carnosic acid is an abietane diterpenoid that is abieta-8,11,13-triene substituted by hydroxy groups at positions 11 and 12 and a carboxy group at position 20. It is isolated from rosemary (Rosmarinus officinalis) and common sage (Salvia officinalis) and exhibits anti-angiogenic, antineoplastic, antioxidant and anti-HIV activity. It has a role as an antineoplastic agent, an antioxidant, a HIV protease inhibitor, an angiogenesis modulating agent, an apoptosis inducer, a plant metabolite, an anti-inflammatory agent and a food preservative. It is an abietane diterpenoid, a carbotricyclic compound, a member of catechols and a monocarboxylic acid. It is a conjugate acid of a carnosate. Carnosic acid is a natural product found in Salvia tomentosa, Illicium verum, and other organisms with data available. See also: Rosemary (part of). An abietane diterpenoid that is abieta-8,11,13-triene substituted by hydroxy groups at positions 11 and 12 and a carboxy group at position 20. It is isolated from rosemary (Rosmarinus officinalis) and common sage (Salvia officinalis) and exhibits anti-angiogenic, antineoplastic, antioxidant and anti-HIV activity. D020011 - Protective Agents > D000975 - Antioxidants D000890 - Anti-Infective Agents

Stigmasterol

C29H48O (412.3705)

Stigmasterol is a phytosterol, meaning it is steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15\\%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. Stigmasterol is found to be associated with phytosterolemia, which is an inborn error of metabolism. Stigmasterol is a 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. It has a role as a plant metabolite. It is a 3beta-sterol, a stigmastane sterol, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. It derives from a hydride of a stigmastane. Stigmasterol is a natural product found in Ficus auriculata, Xylopia aromatica, and other organisms with data available. Stigmasterol is a steroid derivative characterized by the hydroxyl group in position C-3 of the steroid skeleton, and unsaturated bonds in position 5-6 of the B ring, and position 22-23 in the alkyl substituent. Stigmasterol is found in the fats and oils of soybean, calabar bean and rape seed, as well as several other vegetables, legumes, nuts, seeds, and unpasteurized milk. See also: Comfrey Root (part of); Saw Palmetto (part of); Plantago ovata seed (part of). Stigmasterol is an unsaturated plant sterol occurring in the plant fats or oils of soybean, calabar bean, and rape seed, and in a number of medicinal herbs, including the Chinese herbs Ophiopogon japonicus (Mai men dong) and American Ginseng. Stigmasterol is also found in various vegetables, legumes, nuts, seeds, and unpasteurized milk. A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol

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.

Euscaphic acid

C30H48O5 (488.3502)

Euscaphic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 19 respectively (the 2alpha,3alpha-stereoisomer). It has been isolated from the leaves of Rosa laevigata. It has a role as a plant metabolite. It is a pentacyclic triterpenoid, a hydroxy monocarboxylic acid and a triol. It derives from a hydride of an ursane. Euscaphic acid is a natural product found in Ternstroemia gymnanthera, Rhaphiolepis deflexa, and other organisms with data available. A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 19 respectively (the 2alpha,3alpha-stereoisomer). It has been isolated from the leaves of Rosa laevigata. Euscaphic acid is found in herbs and spices. Euscaphic acid is a constituent of Coleus amboinicus (Cuban oregano). Constituent of Coleus amboinicus (Cuban oregano). Euscaphic acid is found in loquat and herbs and spices. Euscaphic acid, a DNA polymerase inhibitor, is a triterpene from the root of the R. alceaefolius Poir. Euscaphic inhibits calf DNA polymerase α (pol α) and rat DNA polymerase β (pol β) with IC50 values of 61 and 108 μM[1]. Euscaphic acid induces apoptosis[2]. Euscaphic acid, a DNA polymerase inhibitor, is a triterpene from the root of the R. alceaefolius Poir. Euscaphic inhibits calf DNA polymerase α (pol α) and rat DNA polymerase β (pol β) with IC50 values of 61 and 108 μM[1]. Euscaphic acid induces apoptosis[2].

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.

Globulol

C15H26O (222.1984)

Ledol is a sesquiterpenoid. Ledol is a natural product found in Waitzia acuminata, Aloysia gratissima, and other organisms with data available. Ledol is found in allspice. Ledol is a constituent of Valeriana officinalis (valerian), Piper species and others. Constituent of Eucalyptus globulus (Tasmanian blue gum). Globulol is found in allspice and pepper (spice). Ledol ((+)-Ledol) is an antifungal agent that can be isolated from the essential oil fractions of Rhododendron tomentosum. Ledol is also the expectorant and antitussive agent, which is simultaneously responsible for adverse reactions such as dizziness, nausea and vomiting[1]. Ledol ((+)-Ledol) is an antifungal agent that can be isolated from the essential oil fractions of Rhododendron tomentosum. Ledol is also the expectorant and antitussive agent, which is simultaneously responsible for adverse reactions such as dizziness, nausea and vomiting[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].

alpha-Farnesene

C15H24 (204.1878)

alpha-Farnesene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3E,6E)-alpha-Farnesene, also known as trans-alpha-Farnesene, is a sweet, bergamot, and citrus tasting flavouring ingredient. (3E,6E)-alpha-Farnesene is a constituent of the natural coating of apples and pears and other fruit. It has been identified in gingers, cottonseeds, common oregano, sweet oranges, spearmints, guava, pomes, and pears. This could make (3E,6E)-alpha-farnesene a potential biomarker for the consumption of these foods. Alpha-farnesene is a farnesene that is 1,3,6,10-tetraene substituted by methyl groups at positions 3, 7 and 11 respectively. alpha-Farnesene is a natural product found in Eupatorium cannabinum, Lonicera japonica, and other organisms with data available. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of). Constituent of the natural coating of apples and pears and other fruit. Flavouring ingredient. (3E,6E)-alpha-Farnesene is found in many foods, some of which are cottonseed, spearmint, ginger, and fruits.

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].

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].

Guaiol

C15H26O (222.1984)

Guaiol is a guaiane sesquiterpenoid. Guaiol is a natural product found in Philotheca fitzgeraldii, Aristolochia asclepiadifolia, and other organisms with data available. See also: Cannabis sativa subsp. indica top (part of). Guaiol is a sesquiterpene alcohol that has been found in several traditional Chinese medicinal plants and has antiproliferative, pro-autophagic, insect repellent, and insecticidal biological activities[1][2][3]. Guaiol is a sesquiterpene alcohol that has been found in several traditional Chinese medicinal plants and has antiproliferative, pro-autophagic, insect repellent, and insecticidal biological activities[1][2][3].

Valencene

C15H24 (204.1878)

(+)-valencene is a carbobicyclic compound and sesquiterpene that is 1,2,3,4,4a,5,6,7-octahydronaphthalene which is substituted a prop-1-en-2-yl group at position 3 and by methyl groups at positions 4a and 5 (the 3R,4aS,5R- diastereoisomer). It is a sesquiterpene, a carbobicyclic compound and a polycyclic olefin. Valencene is a natural product found in Xylopia sericea, Helichrysum odoratissimum, and other organisms with data available. Valencene is found in citrus. Valencene is a constituent of orange oil Valencene is a sesquiterpene isolated from Cyperus rotundus, possesses antiallergic, antimelanogenesis, anti-infammatory, and antioxidant activitivies. Valencene inhibits the exaggerated expression of Th2 chemokines and proinflammatory chemokines through blockade of the NF-κB pathway. Valencene is used to flavor foods and drinks[1][2][3].

Cirsimaritin

C17H14O6 (314.079)

Cirsimaritin, also known as 4,5-dihydroxy-6,7-dimethoxyflavone or scrophulein, 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, cirsimaritin is considered to be a flavonoid lipid molecule. Cirsimaritin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cirsimaritin can be found in a number of food items such as italian oregano, lemon verbena, winter savory, and rosemary, which makes cirsimaritin a potential biomarker for the consumption of these food products.

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].

alpha-Humulene

C15H24 (204.1878)

alpha-Humulene, also known as alpha-caryophyllene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, alpha-humulene is considered to be an isoprenoid lipid molecule. alpha-Humulene is found in allspice. alpha-Humulene is a constituent of many essential oils including hops (Humulus lupulus) and cloves (Syzygium aromaticum). (1E,4E,8E)-alpha-humulene is the (1E,4E,8E)-isomer of alpha-humulene. Humulene is a natural product found in Nepeta nepetella, Teucrium montanum, and other organisms with data available. See also: Caryophyllene (related). α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1]. α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1].

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].

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].

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.

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].

(+)-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].

(S)-3-Octanol

C8H18O (130.1358)

Present in Mentha subspecies oils, sage, soybeans, porcini (Boletus edulis), wines and other foodstuffs. Flavouring agent. 3-Octanol is found in many foods, some of which are mushrooms, soy bean, rosemary, and alcoholic beverages. 3-Octanol is found in alcoholic beverages. 3-Octanol is present in Mentha species oils, sage, soybeans, porcini (Boletus edulis), wines and other foodstuffs. 3-Octanol is a flavouring agent

alpha-Cadinol

C15H26O (222.1984)

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

1-Methoxy-4-(2-propenyl)benzene

C10H12O (148.0888)

1-Methoxy-4-(2-propenyl)benzene, also known as methylchavicol or estragol, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. 1-Methoxy-4-(2-propenyl)benzene is a sweet, alcohol, and anise tasting compound. 1-Methoxy-4-(2-propenyl)benzene is found, on average, in the highest concentration within a few different foods, such as anises, fennels, and sweet basils and in a lower concentration in cumins, tarragons, and parsley. 1-Methoxy-4-(2-propenyl)benzene has also been detected, but not quantified, in several different foods, such as citrus, chinese cinnamons, caraway, fats and oils, and cloves. This could make 1-methoxy-4-(2-propenyl)benzene a potential biomarker for the consumption of these foods. 1-Methoxy-4-(2-propenyl)benzene, with regard to humans, has been linked to the inborn metabolic disorder celiac disease. Constituent of many essential oils. Found in apple, bilberry and orange fruits and juices. Flavouring agent. Estragole (4-Allylanisole), a relatively nontoxic volatile terpenoid ether, is a major component of the essential oil of many plants. Estragole dose-dependently blocks nerve excitability[1]. Estragole displays anti-toxoplasma activity[2]. Estragole (4-Allylanisole), a relatively nontoxic volatile terpenoid ether, is a major component of the essential oil of many plants. Estragole dose-dependently blocks nerve excitability[1]. Estragole displays anti-toxoplasma activity[2].

Santin

C18H16O7 (344.0896)

A trimethoxyflavone that is flavone substituted by methoxy groups at positions 3, 6 and 4 and hydroxy groups at positions 5 and 7 respectively.

(±)-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].

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 .

(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].

Ethyl pentyl ketone

C8H16O (128.1201)

Ethyl pentyl ketone, also known as 3-oxooctane or eak, is a member of the class of compounds known as ketones. Ketones are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, ethyl pentyl ketone is considered to be an oxygenated hydrocarbon lipid molecule. Ethyl pentyl ketone is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Ethyl pentyl ketone is a sweet, butter, and fresh tasting compound and can be found in a number of food items such as rosemary, hyssop, spearmint, and rocket salad (sspecies), which makes ethyl pentyl ketone a potential biomarker for the consumption of these food products. Ethyl pentyl ketone can be found primarily in feces and saliva. Ethyl pentyl ketone exists in all eukaryotes, ranging from yeast to humans. Ethyl pentyl ketone, also known as 3-oxooctane or EAK, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, ethyl pentyl ketone is considered to be an oxygenated hydrocarbon lipid molecule. A dialkyl ketone that is octane in which the two methylene protons at position 3 have been replaced by an oxo group. Ethyl pentyl ketone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Ethyl pentyl ketone has been detected, but not quantified, in cardamoms and lemons. This could make ethyl pentyl ketone a potential biomarker for the consumption of these foods. Ethyl pentyl ketone, with regard to humans, has been linked to the inborn metabolic disorder celiac disease.

Longifolene

C15H24 (204.1878)

Longifolene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Longifolene is a sweet, fir needle, and medical tasting compound found in corn, mandarin orange (clementine, tangerine), rosemary, and star anise, which makes longifolene a potential biomarker for the consumption of these food products. Longifolene is the common (or trivial) chemical name of a naturally occurring, oily Liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73¬∞. The other enantiomer (optical rotation ‚àí42.73¬∞) is found in small amounts in certain fungi and liverworts . Longifolene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Longifolene is a sweet, fir needle, and medical tasting compound found in corn, mandarin orange (clementine, tangerine), rosemary, and star anise, which makes longifolene a potential biomarker for the consumption of these food products. Longifolene is the common (or trivial) chemical name of a naturally occurring, oily liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts . (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1]. (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1]. (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1].

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.

(+)-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-Cubebene

C15H24 (204.1878)

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

beta-Cubebene

C15H24 (204.1878)

Beta-cubebene, also known as (-)-B-cubebene, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Beta-cubebene is a citrus and fruity tasting compound and can be found in a number of food items such as sweet basil, roman camomile, pot marjoram, and sweet bay, which makes beta-cubebene a potential biomarker for the consumption of these food products. Beta-cubebene can be found primarily in saliva. Piper cubeba, cubeb or tailed pepper is a plant in genus Piper, cultivated for its fruit and essential oil. It is mostly grown in Java and Sumatra, hence sometimes called Java pepper. The fruits are gathered before they are ripe, and carefully dried. Commercial cubebs consist of the dried berries, similar in appearance to black pepper, but with stalks attached – the "tails" in "tailed pepper". The dried pericarp is wrinkled, and its color ranges from grayish brown to black. The seed is hard, white and oily. The odor of cubebs is described as agreeable and aromatic and the taste as pungent, acrid, slightly bitter and persistent. It has been described as tasting like allspice, or like a cross between allspice and black pepper . beta-Cubebene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

(-)-alpha-Curcumene

C15H22 (202.1721)

1-[(2R)-hex-5-en-2-yl]-4-methylbenzene is a member of the class of compounds known as aromatic monoterpenoids. Aromatic monoterpenoids are monoterpenoids containing at least one aromatic ring. (-)-alpha-Curcumene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

alpha-eudesmol

C15H26O (222.1984)

A eudesmane sesquiterpenoid in which the eudesmane skeleton carries a hydroxy substituent at C-11 and has a double bond between C-3 and C-4.

(-)-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.

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].

Vetispiradiene

C15H24 (204.1878)

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].

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.

alpha-Guaiene

C15H24 (204.1878)

Constituent of guaiac wood oil (Bulnesia sarmienti). alpha-Guaiene is found in many foods, some of which are herbs and spices, sweet basil, burdock, and pepper (spice). alpha-Guaiene is found in burdock. alpha-Guaiene is a constituent of guaiac wood oil (Bulnesia sarmienti)

(+)-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.

Bicyclogermacrene

C15H24 (204.1878)

Constituent of the peel oil of Citrus junos (yuzu). Bicyclogermacrene is found in many foods, some of which are common oregano, lemon balm, hyssop, and orange mint. Bicyclogermacrene is found in citrus. Bicyclogermacrene is a constituent of the peel oil of Citrus junos (yuzu).

Isomenthone

C10H18O (154.1358)

Isomenthone (CAS: 491-07-6) is a flavouring ingredient and is found in many foods, including blackcurrant, orange mint, peppermint, and spearmint. (+)-Isomenthone is found in American pennyroyal oil (Hedeoma pulegioides), Mentha arvensis, Pelargonium tomentosum, and other essential oils. (-)-Isomenthone is found in cornmint, the oil of Mentha pulegium, and herbs and spices. Isolated from oils of Mentha arvensis, Mentha pulegium, Hedeoma pulegioides and others. (-)-Isomenthone is found in cornmint, spearmint, and herbs and spices. (+)-Isomenthone is an isomenthone isolated from Ziziphora clinopodioides Lam.. (+)-Isomenthone is an isomer of L-Menthone[1][2]. (+)-Isomenthone is an isomenthone isolated from Ziziphora clinopodioides Lam.. (+)-Isomenthone is an isomer of L-Menthone[1][2]. (+)-Isomenthone is an isomenthone isolated from Ziziphora clinopodioides Lam.. (+)-Isomenthone is an isomer of L-Menthone[1][2]. (+)-Isomenthone is an isomenthone isolated from Ziziphora clinopodioides Lam.. (+)-Isomenthone is an isomer of L-Menthone[1][2].

(+)-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

(-)-cis-Carveol

C10H16O (152.1201)

(-)-cis-Carveol is found in citrus. (-)-cis-Carveol is a constituent of Valencia orange oil (Citrus sinensis). (-)-cis-Carveol is a flavouring agent Constituent of Valencia orange oil (Citrus sinensis). Flavouring agent. (-)-cis-Carveol is found in citrus.

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 .

10-epi-gamma-eudesmol

C15H26O (222.1984)

Flavouring compound [Flavornet]

β-Pinene

C10H16 (136.1252)

An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants. Widely distributed in plants, usually associated with a-Pinene JPV84-W but in smaller amounts. Found in lime peel oil, ginger, nutmeg, mace, bitter fennel, rosemary and sage. Flavour ingredient 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].

Cedrelanol

C15H26O (222.1984)

A cadinane sesquiterpenoid that is cadin-4-ene carrying a hydroxy substituent at position 10.

Stirrup

C15H26O (222.1984)

C26170 - Protective Agent > C275 - Antioxidant Acquisition and generation of the data is financially supported in part by CREST/JST. Farnesol is a sesquiterpene alcohol that modulates cell-to-cell communication in Candida albicans, and has the activity in inhibiting bacteria. Farnesol is a sesquiterpene alcohol that modulates cell-to-cell communication in Candida albicans, and has the activity in inhibiting bacteria. 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]. trans-Nerolidol is a sesquiterpene alcohol. It can be isolated from f aerial parts of Warionia saharae ex Benth. trans-Nerolidol improves the anti-proliferative effect of Doxorubicin (HY-15142A) against intestinal cancer cells in vitro. trans-Nerolidol also has anti-fungal activity[1][2]. trans-Nerolidol is a sesquiterpene alcohol. It can be isolated from f aerial parts of Warionia saharae ex Benth. trans-Nerolidol improves the anti-proliferative effect of Doxorubicin (HY-15142A) against intestinal cancer cells in vitro. trans-Nerolidol also has anti-fungal activity[1][2].

Artemetin

C20H20O8 (388.1158)

Artemetin is found in common verbena. Artemetin is a constituent of Artemisia species, Kuhnia eupatorioides (preferred genus name Brickellia), Achillea species, Brickellia species and others in the Compositae [CCD] Constituent of Artemisia subspecies, Kuhnia eupatorioides (preferred genus name Brickellia), Achillea subspecies, Brickellia subspecies and others in the Compositae [CCD]. Artemetin is found in common verbena. Artemetin is a member of flavonoids and an ether. Artemetin is a natural product found in Achillea santolina, Psiadia viscosa, and other organisms with data available. Artemitin is a flavonol found in Laggera pterodonta (DC.) Benth., with antioxidative, anti-inflammatory, and antiviral activity[1]. Artemitin is a flavonol found in Laggera pterodonta (DC.) Benth., with antioxidative, anti-inflammatory, and antiviral activity[1].

Spathulenol

C15H24O (220.1827)

Spathulenol is a tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7. It has a role as a volatile oil component, a plant metabolite, an anaesthetic and a vasodilator agent. It is a sesquiterpenoid, a carbotricyclic compound, a tertiary alcohol and an olefinic compound. Spathulenol is a natural product found in Xylopia aromatica, Xylopia emarginata, and other organisms with data available. See also: Chamomile (part of). A tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7. Spathulenol is found in alcoholic beverages. Spathulenol is a constituent of Salvia sclarea (clary sage).

Salvigenin

C18H16O6 (328.0947)

Salvigenin, also known as psathyrotin or 7-O-methylpectolinarigenin, 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, salvigenin is considered to be a flavonoid lipid molecule. Salvigenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Salvigenin has been detected, but not quantified in, several different foods, such as rosemaries, mandarin orange (clementine, tangerine), common sages, sweet basils, and peppermints. This could make salvigenin a potential biomarker for the consumption of these foods. BioTransformer predicts that salvigenin is a product of tetramethylscutellarein metabolism via an O-dealkylation reaction catalyzed by CYP1A2, CYP2C9, CYP2C19, CYP2D6, CYP2E1, and CYP3A4 enzymes (PMID: 30612223). Salvigenin, also known as 5-hydroxy-6,7,4-trimethoxyflavone or 7-O-methylpectolinarigenin, 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, salvigenin is considered to be a flavonoid lipid molecule. Salvigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Salvigenin can be found in a number of food items such as sweet basil, mandarin orange (clementine, tangerine), common sage, and peppermint, which makes salvigenin a potential biomarker for the consumption of these food products. Salvigenin is a trimethoxyflavone that is scutellarein in which the hydroxy groups at positions 4, 6, and 7 are replaced by methoxy groups. It has a role as an autophagy inducer, an apoptosis inhibitor, an antilipemic drug, an immunomodulator, an antineoplastic agent, a neuroprotective agent, a hypoglycemic agent and a plant metabolite. It is a trimethoxyflavone and a monohydroxyflavone. It is functionally related to a scutellarein. Salvigenin is a natural product found in Liatris elegans, Achillea santolina, and other organisms with data available. See also: Tangerine peel (part of). A trimethoxyflavone that is scutellarein in which the hydroxy groups at positions 4, 6, and 7 are replaced by methoxy groups. Salvigenin is a natural polyphenolic compound, with neuroprotective effect. Salvigenin has antitumor cytotoxic and immunomodulatory properties. Salvigenin inhibits H2O2-induced cell apoptosis[1][2]. Salvigenin is a natural polyphenolic compound, with neuroprotective effect. Salvigenin has antitumor cytotoxic and immunomodulatory properties. Salvigenin inhibits H2O2-induced cell apoptosis[1][2].

Pulegone

C10H16O (152.1201)

Pulegone 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. It is formally classified as a cyclic ketone although it is biochemically a monoterpenoid as it is synthesized via isoprene units. 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 plant cell 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. Pulegone is a hydrophobic, neutral compound that is insoluble in water. It exists as a clear, colorless oil. There are two isomers of Pulegone (the R and the S isomer), with the R isomer being more common. It is used industrially as a food additive and a perfuming agent. Pulegone has a fresh, minty or peppermint odor and a minty, fruity or green taste. It is found naturally in the essential oils of a variety of plants such as Nepeta cataria (catnip), Hedeoma pulegioides (pennyroyal), and Mentha species. It is also found in a number of plant foods and spices such as blackberryies, black currants, bell peppers, cornmint, rosemary, black tea, thyme, orange mint, peppermint, and spearmint, which makes it a potential biomarker for the consumption of these food products. Pulegone is also one of more than 140 terpenes that are found in cannabis plants (PMID:6991645 ). Pulegone, also known as (+)-(R)-pulegone or (1r)-(+)-P-menth-4(8)-en-3-one, 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, pulegone is considered to be an isoprenoid lipid molecule. Pulegone is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Pulegone can be found in a number of food items such as globe artichoke, sacred lotus, garden onion, and rubus (blackberry, raspberry), which makes pulegone a potential biomarker for the consumption of these food products. Pulegone can be found primarily in saliva. Pulegone is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as Nepeta cataria (catnip), Mentha piperita, and pennyroyal. It is classified as a monoterpene . (+)-pulegone is the (5R)-enantiomer of p-menth-4(8)-en-3-one. Pulegone is a natural product found in Hedeoma multiflora, Clinopodium dalmaticum, and other organisms with data available. See also: Agathosma betulina leaf (part of). The (5R)-enantiomer of p-menth-4(8)-en-3-one. 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].

Corosolic acid

C30H48O4 (472.3552)

Colosolic acid is a natural product found in Rhododendron brachycarpum, Psidium, and other organisms with data available.

skrofulein

C17H14O6 (314.079)

Cirsimaritin is a dimethoxyflavone that is flavone substituted by methoxy groups at positions 6 and 7 and hydroxy groups at positions 5 and 4 respectively. It is a dimethoxyflavone and a dihydroxyflavone. It is functionally related to a flavone. Cirsimaritin is a natural product found in Achillea santolina, Schoenia cassiniana, and other organisms with data available. See also: Tangerine peel (part of).

alpha-Carene

C10H16 (136.1252)

Carene is a colorless liquid with a sweet, turpentine-like odor. Floats on water. (USCG, 1999) Car-3-ene is a monoterpene. It derives from a hydride of a carane. 3-Carene is a natural product found in Nepeta nepetella, Xylopia aromatica, and other organisms with data available. See also: Cannabis sativa subsp. indica top (part of). alpha-Carene is found in allspice. alpha-Carene is a flavouring ingredient.Carene, or delta-3-carene, is a bicyclic monoterpene which occurs naturally as a constituent of turpentine, with a content as high as 42\\% depending on the source. Carene has a sweet and pungent odor. It is not soluble in water, but miscible with fats and oils Flavouring ingredient

Carnosic acid

C20H28O4 (332.1987)

Carnosic acid is the major rosemary polyphenol. Carnosic acid appears to enhance the anti-cancer activity of vitamin D(3) and its analogs. Carnosic acid enhances monocytic differentiation of HL60 cells when combined not only with 1alpha,25-dihydroxyvitamin D3 (1,25D3) or 12-O-tetradecanoyl phorbol 13-acetate (TPA) but also with the classic granulocytic inducer all-trans retinoic acid (ATRA). Carnosic acid alone increases the expression of vitamin D receptor (VDR) and retinoid X receptor (RXR) alpha, which was greatly enhanced in the presence of 1alpha,25-dihydroxyvitamin D3 and all-trans retinoic acid. (PMID: 15265684). Isolated from Salvia officinalis (sage) and Rosamarinus officinalis (rosemary). Carnosic acid is found in many foods, some of which are ginger, nutmeg, star anise, and caraway.

gamma-Muurolene

C15H24 (204.1878)

gamma-Muurolene is found in carrot. gamma-Muurolene is a constituent of Pinus sylvestris (Scotch pine).

delta-Amorphene

C15H24 (204.1878)

1(10),4-Cadinadiene is a cadinene (FDB009046) of the delta-serie [FooDB]. A cadinene (FDB009046) of the delta-serie [FooDB]

alpha-Curcumene

C15H22 (202.1721)

alpha-Curcumene belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units

cis-Ocimene

C10H16 (136.1252)

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 odor. It is used in perfumery. cis-beta-Ocimene is found in many foods, some of which are cornmint, sweet orange, sweet basil, and common sage. cis-Ocimene is found in allspice. 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 odor. It is used in perfumery. (Wikipedia

(S)-p-Menth-1-en-4-ol

C10H18O (154.1358)

(S)-p-Menth-1-en-4-ol occurs in many essential oils, e.g. lavende Occurs in many essential oils, e.g. lavender 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].

1-Epi-alpha-gurjunene

C15H24 (204.1878)

1-Epi-alpha-gurjunene is a constituent of Tolu balsam (Myroxylon balsamum var. balsamum). 1-Epi-alpha-gurjunene is a food flavouring. Constituent of Tolu balsam (Myroxylon balsamum variety balsamum). Food flavouring

1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester

C48H76O21 (988.4879)

1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester is found in fruits. 1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester is a constituent of Physalis peruviana (Cape gooseberry).

1-Octen-3-yl acetate

C10H18O2 (170.1307)

1-Octen-3-yl acetate is found in fruits. 1-Octen-3-yl acetate is present in Mentha species oils, lavender oil, anise hyssop, mushrooms and melon. 1-Octen-3-yl acetate is a flavouring ingredient. [CCD Present in Mentha subspecies oils, lavender oil, anise hyssop, mushrooms and melon. Flavouring ingredient. [CCD]. 1-Octen-3-yl acetate is found in mushrooms, herbs and spices, and fruits.

(R)-2,5,11-Bisabolatriene

C15H24 (204.1878)

Constituent of the essential oil of Curcuma amada (mango-ginger) and Curcuma xanthorrhiza (Java turmeric). (R)-2,5,11-Bisabolatriene is found in many foods, some of which are herbs and spices, root vegetables, turmeric, and beverages. (R)-2,5,11-Bisabolatriene is found in beverages. (R)-2,5,11-Bisabolatriene is a constituent of the essential oil of Curcuma amada (mango-ginger) and Curcuma xanthorrhiza (Java turmeric)

Citronellyl acetate

C12H22O2 (198.162)

Citronellyl acetate is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]") It is used as a food additive 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].

alpha-Phellandrene

C10H16 (136.1252)

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. Phellandrene is found in many foods, some of which are ceylon cinnamon, peppermint, anise, and dill. alpha-Phellandrene is found in allspice. 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

Cedrelanol

C15H26O (222.1984)

Constituent of Juniperus communis (juniper). Cedrelanol is found in many foods, some of which are fruits, sweet basil, lemon balm, and hyssop. Cedrelanol is found in fruits. Cedrelanol is a constituent of Juniperus communis (juniper).

Cubenol

C15H26O (222.1984)

Cubenol belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units

alpha-Bisabolol

C15H26O (222.1984)

alpha-Bisabolol is a nontoxic sesquiterpene alcohol present in natural essential oil, with anticancer activity. alpha-Bisabolol exerts selective anticancer effect on A549 NSCLC cells (IC50=15 μM) via induction of cell cycle arrest, mitochondrial apoptosis and inhibition of PI3K/Akt signalling pathways. alpha-Bisabolol also strongly induces apoptosis in glioma cells[1][2]. alpha-Bisabolol is a nontoxic sesquiterpene alcohol present in natural essential oil, with anticancer activity. alpha-Bisabolol exerts selective anticancer effect on A549 NSCLC cells (IC50=15 μM) via induction of cell cycle arrest, mitochondrial apoptosis and inhibition of PI3K/Akt signalling pathways. alpha-Bisabolol also strongly induces apoptosis in glioma cells[1][2].

Corosolic acid

C30H48O4 (472.3552)

Corosolic acid, also known as corosolate, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Corosolic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Corosolic acid can be found in guava, loquat, and olive, which makes corosolic acid a potential biomarker for the consumption of these food products. Corosolic acid is a pentacyclic triterpene acid found in Lagerstroemia speciosa. It is similar in structure to ursolic acid, differing only in the fact that it has a 2-alpha-hydroxy attachment . Corosolic acid (Colosolic acid) isolated from the fruit of Cratoegus pinnatifida var. psilosa, was reported to have anticancer activity. Corosolic acid (Colosolic acid) isolated from the fruit of Cratoegus pinnatifida var. psilosa, was reported to have anticancer activity.

Guaiol

C15H26O (222.1984)

Guaiol is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Guaiol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Guaiol is a mild, balsamic, and guaiacwood tasting compound found in ginger, which makes guaiol a potential biomarker for the consumption of this food product. Guaiol or champacol is an organic compound, a sesquiterpenoid alcohol found in several plants, especially in the oil of guaiacum and cypress pine. It is a crystalline solid that melts at 92 °C. Guaiol is one of many terpenes found in Cannabis . Guaiol is a sesquiterpene alcohol that has been found in several traditional Chinese medicinal plants and has antiproliferative, pro-autophagic, insect repellent, and insecticidal biological activities[1][2][3]. Guaiol is a sesquiterpene alcohol that has been found in several traditional Chinese medicinal plants and has antiproliferative, pro-autophagic, insect repellent, and insecticidal biological activities[1][2][3].

delta-Cadinol

C15H26O (222.1984)

Delta-cadinol, also known as delta-cadinol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Delta-cadinol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Delta-cadinol is a herbal tasting compound and can be found in a number of food items such as cloves, parsley, lemon balm, and common sage, which makes delta-cadinol a potential biomarker for the consumption of these food products. Delta-cadinol, also known as δ-cadinol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Delta-cadinol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Delta-cadinol is a herbal tasting compound and can be found in a number of food items such as cloves, parsley, lemon balm, and common sage, which makes delta-cadinol a potential biomarker for the consumption of these food products.

Cuparene

C15H22 (202.1721)

Cuparene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, cuparene is considered to be an isoprenoid lipid molecule. Cuparene can be found in lovage and pepper (spice), which makes cuparene a potential biomarker for the consumption of these food products.

Oleanolic acid methyl ester

C31H50O3 (470.376)

Oleanolic acid methyl ester is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Oleanolic acid methyl ester is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Oleanolic acid methyl ester can be found in common grape, which makes oleanolic acid methyl ester a potential biomarker for the consumption of this food product.

Bornyl acetate

C12H20O2 (196.1463)

Bornyl acetate, also known as bornyl acetic acid, 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. Bornyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Bornyl acetate is a camphor, cedar, and herbal tasting compound and can be found in a number of food items such as nutmeg, rosemary, spearmint, and sunflower, which makes bornyl acetate a potential biomarker for the consumption of these food products. (-)-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]. Bornyl acetate is a potent odorant, exhibiting one of the highest flavor dilution factor (FD factor). Bornyl acetate possesses anti-cancer activity[1][2]. Bornyl acetate is a potent odorant, exhibiting one of the highest flavor dilution factor (FD factor). Bornyl acetate possesses anti-cancer activity[1][2].

D-Camphor

C10H16O (152.1201)

(+)-camphor, also known as formosa camphor or 2-bornanone, 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, (+)-camphor is considered to be an isoprenoid lipid molecule (+)-camphor is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-camphor is a bitter, camphor, and herbal tasting compound and can be found in a number of food items such as sugar apple, sunflower, fennel, and cardamom, which makes (+)-camphor a potential biomarker for the consumption of these food products. C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000890 - Anti-Infective Agents 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].

T-Muurolol

C15H26O (222.1984)

T-muurolol, also known as 10-epi-alpha-muurolol or alpha-epi-muurolol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. T-muurolol is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). T-muurolol is a herbal, spicy, and weak spice tasting compound found in allspice, lemon balm, and white mustard, which makes T-muurolol a potential biomarker for the consumption of these food products.

Ursolic acid (2-alpha-hydroxy-)

C30H48O4 (472.3552)

Nerolidol

C15H26O (222.1984)

Nerolidol is a farnesane sesquiterpenoid that is dodeca-1,6,10-triene which carries methyl groups at positions 3, 7 and 11 and a hydroxy group at position 3. It is a natural product that is present in various flowers and plants with a floral odor. Chemically, it exists in two geometric isomers, trans and cis forms. It is widely used in cosmetics (e.g. shampoos and perfumes), in non-cosmetic products (e.g. detergents and cleansers) and also as a food flavoring agent. It has a role as a flavouring agent, a cosmetic, a pheromone, a neuroprotective agent, an antifungal agent, an anti-inflammatory agent, an antihypertensive agent, an antioxidant, a volatile oil component, an insect attractant and a herbicide. It is a farnesane sesquiterpenoid, a tertiary allylic alcohol and a volatile organic compound. Nerolidol is a natural product found in Xylopia sericea, Rhododendron calostrotum, and other organisms with data available. Nerolidol is found in bitter gourd. Nerolidol is a component of many essential oils. The (S)-enantiomer is the commoner and occurs mostly as the (S)-(E)-isomer. Nerolidol is a flavouring agent. Nerolidol has been shown to exhibit anti-fungal function (A7933).Nerolidol belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units. A nerolidol in which the double bond at position 6 adopts a trans-configuration. 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]. trans-Nerolidol is a sesquiterpene alcohol. It can be isolated from f aerial parts of Warionia saharae ex Benth. trans-Nerolidol improves the anti-proliferative effect of Doxorubicin (HY-15142A) against intestinal cancer cells in vitro. trans-Nerolidol also has anti-fungal activity[1][2]. trans-Nerolidol is a sesquiterpene alcohol. It can be isolated from f aerial parts of Warionia saharae ex Benth. trans-Nerolidol improves the anti-proliferative effect of Doxorubicin (HY-15142A) against intestinal cancer cells in vitro. trans-Nerolidol also has anti-fungal activity[1][2].

Rosmanol

C20H26O5 (346.178)

Rosmanol is a natural product found in Salvia tomentosa, Lepechinia salviae, and other organisms with data available. Rosmanol could inhibit the oxidation of low density lipoprotein (LPL) and significantly inhibit lipopolysaccharide induced iNOS and COX-2 expression, with anti-inflammatory effect. Rosmanol could inhibit the oxidation of low density lipoprotein (LPL) and significantly inhibit lipopolysaccharide induced iNOS and COX-2 expression, with anti-inflammatory effect.

Corosolic_acid

C30H48O4 (472.3552)

Corosolic acid is a triterpenoid. It has a role as a metabolite. Corosolic acid is a natural product found in Ternstroemia gymnanthera, Cunila lythrifolia, and other organisms with data available. See also: Lagerstroemia speciosa leaf (part of). A natural product found particularly in Rhododendron species and Eriobotrya japonica. Corosolic acid (Colosolic acid) isolated from the fruit of Cratoegus pinnatifida var. psilosa, was reported to have anticancer activity. Corosolic acid (Colosolic acid) isolated from the fruit of Cratoegus pinnatifida var. psilosa, was reported to have anticancer activity.

Tormentic_acid

C30H48O5 (488.3502)

Tormentic acid is a triterpenoid. It has a role as a metabolite. Tormentic acid is a natural product found in Debregeasia saeneb, Chaenomeles speciosa, and other organisms with data available. A natural product found in Euscaphis japonica. Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2]. Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2]. Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2].

Corosolic acid

C30H48O4 (472.3552)

Annotation level-1 Corosolic acid (Colosolic acid) isolated from the fruit of Cratoegus pinnatifida var. psilosa, was reported to have anticancer activity. Corosolic acid (Colosolic acid) isolated from the fruit of Cratoegus pinnatifida var. psilosa, was reported to have anticancer activity.

Ursolic Acid

C30H48O3 (456.3603)

Origin: Plant; SubCategory_DNP: Triterpenoids relative retention time with respect to 9-anthracene Carboxylic Acid is 1.636 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.640 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.638 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.642 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.

Menthyl acetate

C12H22O2 (198.162)

?Menthyl acetate (L-Menthyl acetate) is a derivative of L-menthol. ?Menthyl acetate is effective to enhance 5-aminolevulinic acid (ALA) skin permeation[1]. ?Menthyl acetate (L-Menthyl acetate) is a derivative of L-menthol. ?Menthyl acetate is effective to enhance 5-aminolevulinic acid (ALA) skin permeation[1].

neryl acetate

C12H20O2 (196.1463)

Found in citrus, kumquat and pummelo peel oils, ginger, cardamon, clary sage, myrtle leaf and myrtle berries. Flavouring agent 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]. Neryl acetate is a chemical compound isolated from citrus oils[1]. Neryl acetate is a chemical compound isolated from citrus oils[1].

Tormentic acid

C30H48O5 (488.3502)

Tormentic acid, also known as tormentate, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Tormentic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Tormentic acid can be found in loquat and olive, which makes tormentic acid a potential biomarker for the consumption of these food products. Tormentic acid is a bio-active isolate of Luehea divaricata and Agrimonia eupatoria. Tormentic acid derivatives have been synthesized and researched . Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2]. Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2]. Tormentic acid, a triterpene isolated from Rosa rugosa, exerts anti-inflammatory, antihyperlipidemic, and anti-atherogenic properties[1][2].

Maslinic Acid

C30H48O4 (472.3552)

A pentacyclic triterpenoid that is 3alpha-hydroxy epimer of maslinic acid. Isolated from Prunella vulgaris and Isodon japonicus, it exhibits anti-inflammatory activity. Annotation level-1 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.

Curcumene

C15H22 (202.1721)

β-Eudesmol

C15H26O (222.1984)

Beta-eudesmol, also known as beta-selinenol, is a member of the class of compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids are sesquiterpenoids with a structure based on the eudesmane skeleton. Beta-eudesmol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-eudesmol is a green and wood tasting compound and can be found in a number of food items such as common walnut, sweet basil, ginkgo nuts, and burdock, which makes beta-eudesmol a potential biomarker for the consumption of these food products. Beta-Eudesmol is a natural oxygenated sesquiterpene, activates hTRPA1, with an EC50 of 32.5 μM. Beta-Eudesmol increases appetite through TRPA1[1]. Beta-Eudesmol is a natural oxygenated sesquiterpene, activates hTRPA1, with an EC50 of 32.5 μM. Beta-Eudesmol increases appetite through TRPA1[1].