NCBI Taxonomy: 1231669

Leiocarpa (ncbi_taxid: 1231669)

found 183 associated metabolites at genus taxonomy rank level.

Ancestor: Gnaphalieae

Child Taxonomies: Leiocarpa serpens, Leiocarpa tomentosa, Leiocarpa semicalva, Leiocarpa leptolepis, Leiocarpa brevicompta

Acetophenone

Acetophenone, TraceCERT(R), certified reference material

C8H8O (120.0575)


Acetophenone appears as a colorless liquid with a sweet pungent taste and odor resembling the odor of oranges. Freezes under cool conditions. Slightly soluble in water and denser than water. Hence sinks in water. Vapor heavier than air. A mild irritant to skin and eyes. Vapors can be narcotic in high concentrations. Used as a flavoring, solvent, and polymerization catalyst. Acetophenone is a methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group. It has a role as a photosensitizing agent, an animal metabolite and a xenobiotic. Acetophenone is used for fragrance in soaps and perfumes, as a flavoring agent in foods, and as a solvent for plastics and resins. Acute (short-term) exposure to acetophenone vapor may produce skin irritation and transient corneal injury in humans. No information is available on the chronic (long-term), reproductive, developmental, or carcinogenic effects of acetophenone in humans. EPA has classified acetophenone as a Group D, not classifiable as to human carcinogenicity. Acetophenone is a natural product found in Nepeta nepetella, Hypericum hyssopifolium, and other organisms with data available. Acetophenone is a metabolite found in or produced by Saccharomyces cerevisiae. Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances. Acetophenone is found in chicory. Acetophenone is a flavouring ingredient used in fruit flavours. Acetophenone is a raw material for the synthesis of some pharmaceuticals and is also listed as an approved excipient by the U.S. FDA. In a 1994 report released by five top cigarette companies in the U.S., acetophenone was listed as one of the 599 additives to cigarettes. A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group. D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents Flavouring ingredient used in fruit flavours; leavening agent D003879 - Dermatologic Agents Acetophenone is an organic compound with simple structure[1]. Acetophenone is an organic compound with simple structure[1].

   

Camphor

Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (.+/-.)-

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].

   

Ferulic acid

(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

C10H10O4 (194.0579)


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

   

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

Linalool, certified reference material, TraceCERT(R)

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].

   

Palmitic acid

hexadecanoic acid

C16H32O2 (256.2402)


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

   

Polylimonene

1-Methyl-4-(1-methylethenyl)-or 1-methyl-4-isopropenyl-cyclohex-1-ene

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

   

Phytol

2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, (theta-(theta,theta-(E)))-

C20H40O (296.3079)


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

   

Caryophyllene alpha-oxide

[1R-(1R*,4R*,6R*,10S*)]- Caryophylene oxide Caryophyllene epoxide Caryophyllene oxyde Epoxycaryophyllene [1R-(1R*,4R*,6R*,10S*)]-4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane <>-Caryophyllene epoxide <>-Caryophyllene 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].

   

Nonacosane

Nonacosane; Celidoniol, deoxy- (7CI); n-Nonacosane

C29H60 (408.4695)


Nonacosane, also known as CH3-[CH2]27-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Nonacosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, nonacosane is considered to be a hydrocarbon lipid molecule. Nonacosane is a straight-chain hydrocarbon with a molecular formula of C29H60. Nonacosane has been identified within several essential oils. Nonacosane has been detected, but not quantified, in several different foods, such as peachs, ginkgo nuts, cauliflowers, arabica coffee, and lambsquarters. This could make nonacosane a potential biomarker for the consumption of these foods. Nonacosane occurs naturally and has been reported to be a component of a pheromone of Orgyia leucostigma, and evidence suggests it plays a role in the chemical communication of several insects, including the female Anopheles stephensi (a mosquito). It can also be prepared synthetically. It has 1,590,507,121 constitutional isomers. Nonacosane, also known as ch3-[ch2]27-ch3, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, nonacosane is considered to be a hydrocarbon lipid molecule. Nonacosane can be found in a number of food items such as garden tomato (variety), papaya, brussel sprouts, and wild carrot, which makes nonacosane a potential biomarker for the consumption of these food products. Nonacosane occurs naturally and has been reported to be a component of a pheromone of Orgyia leucostigma, and evidence suggests it plays a role in the chemical communication of several insects, including the female Anopheles stephensi (a mosquito) . Nonacosane is a straight-chain alkane comprising of 29 carbon atoms. It has a role as a plant metabolite and a volatile oil component. Nonacosane is a natural product found in Euphorbia larica, Quercus salicina, and other organisms with data available. See also: Moringa oleifera leaf oil (part of). A straight-chain alkane comprising of 29 carbon atoms. Nonacosane, isolated from Baphia massaiensis, exhibits weak activities against E. coli, B. subtilis, P. aeruginosa and S. aureus[1]. Nonacosane, isolated from Baphia massaiensis, exhibits weak activities against E. coli, B. subtilis, P. aeruginosa and S. aureus[1].

   

beta-Geraniol

3,7-Dimethyloctan-1-ol, tetradehydro derivative

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

trans,trans,trans-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene

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

cis-3,7-Dimethyl-2,6-octadien-1-ol, >=97\\%, FCC, FG

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].

   

Octanal

InChI=1/C8H16O/c1-2-3-4-5-6-7-8-9/h8H,2-7H2,1H

C8H16O (128.1201)


Octanal, also known as 1-caprylaldehyde or aldehyde C-8, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, octanal is considered to be a fatty aldehyde lipid molecule. A saturated fatty aldehyde formally arising from reduction of the carboxy group of caprylic acid (octanoic acid). Octanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Octanal exists in all eukaryotes, ranging from yeast to humans. Octanal is an aldehydic, citrus, and fat tasting compound. Octanal is commonly found in high concentrations in limes, caraway, and mandarin orange (clementine, tangerine) and in lower concentrations in wild carrots and carrots. Octanal has also been detected, but not quantified in several different foods, such as cherry tomato, brussel sprouts, alaska wild rhubarbs, sweet marjorams, and sunflowers. N-octylaldehyde is a colorless liquids with a strong fruity odor. Less dense than water and insoluble in water. Flash points 125 °F. Used in making perfumes and flavorings. Octanal is a saturated fatty aldehyde formally arising from reduction of the carboxy group of caprylic acid (octanoic acid). It has a role as a plant metabolite. It is a saturated fatty aldehyde, a n-alkanal and a medium-chain fatty aldehyde. Octanal is a natural product found in Eupatorium cannabinum, Thymus zygioides, and other organisms with data available. Octanal is a metabolite found in or produced by Saccharomyces cerevisiae. Isolated from various plant oils especies Citrus subspeciesand is also present in kumquat peel oil, cardamom, coriander, caraway and other herbs. Flavouring agent, used in artificial citrus formulations A saturated fatty aldehyde formally arising from reduction of the carboxy group of caprylic acid (octanoic acid). A - Alimentary tract and metabolism > A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents Octanal is an aromatic aldehyde, with antioxidant and antimicrobial activities. Octanal shows cytotoxicity against Hela cells[1]. Octanal is an aromatic aldehyde, with antioxidant and antimicrobial activities. Octanal shows cytotoxicity against Hela cells[1].

   

Lauric aldehyde

InChI=1/C12H24O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h12H,2-11H2,1H

C12H24O (184.1827)


Dodecanal is a long-chain fatty aldehyde that is dodecane in which two hydrogens attached to a terminal carbon are replaced by an oxo group. It has a role as a plant metabolite. It is a 2,3-saturated fatty aldehyde, a medium-chain fatty aldehyde and a long-chain fatty aldehyde. It derives from a hydride of a dodecane. Dodecanal is a natural product found in Mikania cordifolia, Zingiber mioga, and other organisms with data available. Occurs in peel oil from Citrus subspecies and kumquatand is also present in ginger, coriander, chervil and scallop. Flavouring agent. Lauric aldehyde is found in many foods, some of which are mollusks, rocket salad (sspecies), sweet orange, and fruits. Lauric aldehyde is found in citrus. Lauric aldehyde occurs in peel oil from Citrus species and kumquat. Also present in ginger, coriander, chervil and scallop. Lauric aldehyde is a flavouring agent. A long-chain fatty aldehyde that is dodecane in which two hydrogens attached to a terminal carbon are replaced by an oxo group.

   

3-Hexen-1-ol

(3Z)-3-Hexen-1-ol ; (z)-3-hexen-1-o;3-Hexen-1-ol;Cis-3-Hexenol

C6H12O (100.0888)


(Z)-hex-3-en-1-ol is a hex-3-en-1-ol in which the double bond adopts a Z-configuration. Also known as leaf alcohol, it is emitted by green plants upon mechanical damage. Used as a flavourant in tea. It has a role as an insect attractant, a plant metabolite and a fragrance. cis-3-Hexen-1-ol is a natural product found in Lonicera japonica, Santolina corsica, and other organisms with data available. cis-3-hexen-1-ol is a metabolite found in or produced by Saccharomyces cerevisiae. 3-Hexen-1-ol, also known as 1-hydroxy-3-hexene, is a colourless oily liquid with an intense grassy-green odour of freshly cut green grass and leaves. It is produced in small amounts by most plants and it acts as an attractant to many predatory insects. 3-Hexen-1-ol is a very important aroma compound that is used in fruit and vegetable flavours and in perfumes. The yearly production is about 30 tonnes. 3-Hexen-1-ol is found in black elderberry. It is used as tea flavourant. Preferred to (E)-isomer in perfumes and flavours to add natural `green notes. Occurs in geranium, tea, citrus and other oils, and many fruits, e.g. banana, concord grape, quince. (Z)-3-Hexen-1-ol is found in many foods, some of which are allspice, dill, citrus, and garden tomato (variety). A hex-3-en-1-ol in which the double bond adopts a Z-configuration. Also known as leaf alcohol, it is emitted by green plants upon mechanical damage. Used as a flavourant in tea. cis-3-Hexen-1-ol ((Z)-3-Hexen-1-ol) is a green grassy smelling compound found in many fresh fruits and vegetables. cis-3-Hexen-1-ol is widely used as an added flavor in processed food to provide a fresh green quality. cis-3-Hexen-1-ol is an attractant to various insects[1][2]. cis-3-Hexen-1-ol ((Z)-3-Hexen-1-ol) is a green grassy smelling compound found in many fresh fruits and vegetables. cis-3-Hexen-1-ol is widely used as an added flavor in processed food to provide a fresh green quality. cis-3-Hexen-1-ol is an attractant to various insects[1][2].

   

(+)-alpha-Pinene

(R)-(+)--Pinene;(+)--Pinene; (1R)-(+)--Pinene; (1R)--Pinene; (1R,5R)-(+)--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].

   

Stearic acid

1-Heptadecanecarboxylic acid

C18H36O2 (284.2715)


Stearic acid, also known as stearate or N-octadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, stearic acid is considered to be a fatty acid lipid molecule. Stearic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Stearic acid can be synthesized from octadecane. Stearic acid is also a parent compound for other transformation products, including but not limited to, 3-oxooctadecanoic acid, (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoic acid, and 16-methyloctadecanoic acid. Stearic acid can be found in a number of food items such as green bell pepper, common oregano, ucuhuba, and babassu palm, which makes stearic acid a potential biomarker for the consumption of these food products. Stearic acid can be found primarily in most biofluids, including urine, feces, cerebrospinal fluid (CSF), and sweat, as well as throughout most human tissues. Stearic acid exists in all living species, ranging from bacteria to humans. In humans, stearic acid is involved in the plasmalogen synthesis. Stearic acid is also involved in mitochondrial beta-oxidation of long chain saturated fatty acids, which is a metabolic disorder. Moreover, stearic acid is found to be associated with schizophrenia. Stearic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Stearic acid ( STEER-ik, stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain and has the IUPAC name octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. The triglyceride derived from three molecules of stearic acid is called stearin . Stearic acid, also known as octadecanoic acid or C18:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid (its ester is called stearate) is a saturated fatty acid that has 18 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. It exists as a waxy solid. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks, up to the 16-carbon palmitate, via the enzyme complex fatty acid synthase (FA synthase), at which point a fatty acid elongase is needed to further lengthen it. After synthesis, there are a variety of reactions it may undergo, including desaturation to oleate via stearoyl-CoA desaturase (PMID: 16477801). Stearic acid is found in all living organisms ranging from bacteria to plants to animals. It is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. For example, it is a component of cocoa butter and shea butter. It is used as a food additive, in cleaning and personal care products, and in lubricants. Its name comes from the Greek word stear, which means ‚Äòtallow‚Äô or ‚Äòhard fat‚Äô. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

   

Oleic acid

Emersol 221 low titer white oleic acid

C18H34O2 (282.2559)


Oleic acid (or 9Z)-Octadecenoic acid) is an unsaturated C-18 or an omega-9 fatty acid that is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. The name derives from the Latin word oleum, which means oil. Oleic acid is the most abundant fatty acid in human adipose tissue, and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils. Triglycerides of oleic acid represent the majority of olive oil (about 70\\\\%). Oleic acid triglycerides also make up 59–75\\\\% of pecan oil, 61\\\\% of canola oil, 36–67\\\\% of peanut oil, 60\\\\% of macadamia oil, 20–80\\\\% of sunflower oil, 15–20\\\\% of grape seed oil, sea buckthorn oil, 40\\\\% of sesame oil, and 14\\\\% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80\\\\%) and canola oil (70\\\\%) also have been developed. consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, the ability of oleic acid to raise HDL is still debated. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. It is also used as an emulsifying agent in foods and pharmaceuticals. Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Major constituent of plant oils e.g. olive oil (ca. 80\\\\%), almond oil (ca. 80\\\\%) and many others, mainly as glyceride. Constituent of tall oiland is also present in apple, melon, raspberry oil, tomato, banana, roasted peanuts, black tea, rice bran, cardamon, plum brandy, peated malt, dairy products and various animal fats. Component of citrus fruit coatings. Emulsifying agent in foods CONFIDENCE standard compound; INTERNAL_ID 290 COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

   

Linoleic acid

C18:2 9C, 12C Omega6 todos cis-9,12-octadienoico

C18H32O2 (280.2402)


Linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes (From Stedman, 26th ed). Linoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups (−CH=CH−) are cis. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.[5] Linoleic acid is a polyunsaturated, omega-6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents.[2] It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid.[6] It is one of two essential fatty acids for humans, who must obtain it through their diet,[7] and the most essential, because the body uses it as a base to make the others. The word "linoleic" derives from Latin linum 'flax', and oleum 'oil', reflecting the fact that it was first isolated from linseed oil.

   

(+)-Camphor

(+)-Camphor;(+)-bornan-2-one;(+)-camphor;(1R)-(+)-camphor;(R)-(+)-camphor;(R)-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].

   

Phenylacetaldehyde

alpha-Phenylacetaldehyde

C8H8O (120.0575)


Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma- active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. Therefore will eventually be hydrolyzed and oxidized to yield phenylacetic acid that will be excreted primarily in the urine in conjugated form. (PMID: 16910727, 7818768, 15606130). Found in some essential oils, e.g. Citrus subspecies, Tagetes minuta (Mexican marigold) and in the mushroom Phallus impudicus (common stinkhorn). Flavouring ingredient COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

Decanal

N-Decanal (capric aldehyde)

C10H20O (156.1514)


Decanal, also known as 1-decyl aldehyde or capraldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, decanal is considered to be a fatty aldehyde lipid molecule. Decanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Decanal exists in all eukaryotes, ranging from yeast to humans. Decanal is a sweet, aldehydic, and citrus tasting compound. Decanal is found, on average, in the highest concentration within a few different foods, such as corianders, dills, and gingers and in a lower concentration in limes, sweet oranges, and safflowers. Decanal has also been detected, but not quantified, in several different foods, such as fishes, cauliflowers, citrus, fats and oils, and lemon grass. This could make decanal a potential biomarker for the consumption of these foods. Decanal is a potentially toxic compound. Decanal, with regard to humans, has been found to be associated with several diseases such as uremia, asthma, and perillyl alcohol administration for cancer treatment; decanal has also been linked to the inborn metabolic disorder celiac disease. Decanal occurs naturally and is used in fragrances and flavoring. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Constituent of Cassia, Neroli and other oils especies citrus peel oilsand is also present in coriander leaf or seed, caviar, roast turkey, roast filbert, green tea, fish oil, hop oil and beer. Flavouring agent Decyl aldehyde is a simple ten-carbon aldehyde. Decyl aldehyde is a bacterial luciferase substrate. Decyl aldehyde is a simple ten-carbon aldehyde. Decyl aldehyde is a bacterial luciferase substrate.

   

Octanol

Octyl alcohol normal-primary

C8H18O (130.1358)


1-Octanol, also known as octan-1-ol, is the organic compound with the molecular formula CH3(CH2)7OH. It is a fatty alcohol. Many other isomers are also known generically as octanols. Octanol is mainly produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. This route is known as the Ziegler alcohol synthesis. Octanol also occurs naturally in the form of esters in some essential oils. Octanol and water are immiscible. The distribution of a compound between water and octanol is used to calculate the partition coefficient (logP) of that molecule. Water/octanol partitioning is a good approximation of the partitioning between the cytosol and lipid membranes of living systems. Octanol is a colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. It is also one of many compounds derived from tobacco and tobacco smoke and shown to increase the permeability of the membranes of human lung fibroblasts (PMID 7466833). Occurs in the form of esters in some essential oils. Flavouring agent. 1-Octanol is found in many foods, some of which are common wheat, lime, tea, and corn. D012997 - Solvents 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2]. 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2].

   

Naphthalene

naphthalene

C10H8 (128.0626)


Naphthalene, also known as naftaleno or albocarbon, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Naphthalene is possibly neutral. Naphthalene is a dry, pungent, and tar tasting compound. Naphthalene is found, on average, in the highest concentration within a few different foods, such as black walnuts, corns, and cloves. Naphthalene has also been detected, but not quantified, in several different foods, such as green bell peppers, orange bell peppers, rices, yellow bell peppers, and red bell peppers. This could make naphthalene a potential biomarker for the consumption of these foods. Naphthalene was once the primary ingredient in mothballs, though its use has largely been replaced in favor of alternatives such as 1,4-dichlorobenzene. Naphthalene is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Inhalation of naphthalene vapor has been associated with headaches, nausea, vomiting and dizziness. Naphthalene is the most abundant single component of coal tar so most of it is now industrially derived from coal tar. Aside from coal tar, trace amounts of naphthalene are produced by magnolias and some species of deer, as well as the Formosan subterranean termite, possibly produced by the termite as a repellant against "ants, poisonous fungi and nematode worms."[23] Some strains of the endophytic fungus Muscodor albus produce naphthalene among a range of volatile organic compounds, while Muscodor vitigenus produces naphthalene almost exclusively (PMID:12427963). Found in many essential oils

   

p-Cymene

1-Methyl-4-(1-methylethyl)-benzene

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.

   

gamma-Humulene

(1E,6Z)-1,8,8-trimethyl-5-methylidenecycloundeca-1,6-diene (1E,6Z)-humula-1(11),4(13),5-triene

C15H24 (204.1878)


   

1-Hexadecanol

Normal primary hexadecyl alcohol

C16H34O (242.261)


Cetyl alcohol, also known as 1-hexadecanol and palmityl alcohol, is a solid organic compound and a member of the alcohol class of compounds. Its chemical formula is CH3(CH2)15OH. At room temperature, cetyl alcohol takes the form of a waxy white solid or flakes. It belongs to the group of fatty alcohols. With the demise of commercial whaling, cetyl alcohol is no longer primarily produced from whale oil, but instead either as an end-product of the petroleum industry, or produced from vegetable oils such as palm oil and coconut oil. Production of cetyl alcohol from palm oil gives rise to one of its alternative names, palmityl alcohol. Flavouring ingredient. Cetyl alcohol is found in many foods, some of which are rocket salad (sspecies), soft-necked garlic, bitter gourd, and kohlrabi. 1-Hexadecanol is a fatty alcohol, a lipophilic substrate. 1-Hexadecanol is a fatty alcohol, a lipophilic substrate.

   

Pentadecanal

N-Pentadecanal

C15H30O (226.2297)


Isolated from essential oil of Cinnamomum micranthum and from lemon oil (Citrus limon). Pentadecanal is found in many foods, some of which are lemon, herbs and spices, citrus, and coriander. Pentadecanal is found in citrus. Pentadecanal is isolated from essential oil of Cinnamomum micranthum and from lemon oil (Citrus limon

   

Crepenynic acid

9Z-Octadecen-12-ynoic acid

C18H30O2 (278.2246)


   

Hentriacontane

N-Hentriacontane

C31H64 (436.5008)


Hentriacontane is found in black elderberry. Hentriacontane, also called untriacontane, is a solid, long-chain alkane hydrocarbon with the structural formula CH3(CH2)29CH3. It is found in a variety of plants, including peas (pisum sativum), gum arabic (acacia senegal) and others, and also comprises about 8-9\\% of beeswax. It has 10,660,307,791 constitutional isomers Hentriacontane, also called untriacontane, is a solid, long-chain alkane hydrocarbon with the structural formula CH3(CH2)29CH3. It is found in a variety of plants, including peas (pisum sativum), gum arabic (acacia senegal) and others, and also comprises about 8-9\\% of beeswax. It has 10,660,307,791 constitutional isomers.

   

beta-Caryophyllene

trans-(1R,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene

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-Terpineol

2-(4-Methylcyclohex-3-enyl)propan-2-ol (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].

   

Bicyclogermacrene

(2Z,6Z)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene

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).

   

gamma-Curcumene

.delta.-bisabolene

C15H24 (204.1878)


A sesquiterpene that is cyclohexa-1,3-diene which is substituted by a methyl group at position 1 and a 6-methylhept-5-en-2-yl group at position 4 (the R enantiomer).

   

Manool oxide

Labd-14-ene, 8,13-epoxy-, (13R)-

C20H34O (290.261)


   

Octadecanol

Stearyl alcohol (JP18/NF)

C18H38O (270.2922)


Octadenol is a fatty alcohol present in human and is normally incorporated into plasmalogen lipids. Patients with the autosomal recessive form of rhizomelic chondrodysplasia punctata (AR-RCDP) have elevated octadenol levels, but tended to be normal in other generalized peroxisomal disorders such as neonatal adrenoleukodystrophy and Zellweger syndrome (peroxisomal disorders are deficient in the incorporation of fatty alcohol into plasmalogen lipids). (PMID:8373640). Sjogren-Larsson syndrome is defined by the triad of ichthyosis, mental retardation, and spasticity, and patients accumulate fatty alcohols such as Octadenol in the plasma and cultured fibroblasts. (PMID:2241202). Sjogren-Larsson syndrome (SLS) is an autosomal recessive disorder associated with reduced activity of the fatty alcohol: NAD+ oxidoreductase complex (FAO). SLS patients are specifically deficient in the fatty aldehyde dehydrogenase (FALDH) component of FAO. Measurement of FAO and FALDH detection for SLS, FAO and FALDH activities in cultured skin fibroblasts using the 18-carbon substrate Octadenol is useful for SLS carrier detection. (PMID:1583866). Patients with Sjogren-Larsson syndrome accumulate long-chain fatty alcohol in plasma, with a greater relative accumulation of Octadenol. (PMID:2666627). Solidifying agent for margarine and other foods containing semi-solid fats. Generally recognised as safe (GRAS) status in the USA Product (mixture): D05332 1-Hydroxyoctadecane is an endogenous metabolite. 1-Hydroxyoctadecane is an endogenous metabolite.

   

Pinene

(1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene

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.

   

Spathulenol

1H-Cycloprop(e)azulen-7-ol, decahydro-1,1,7-trimethyl-4-methylene-, (1aR-(1aalpha,4aalpha,7beta,7abeta,7balpha))-

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).

   

beta-Damascenone

1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one; 1-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-2-buten-1-one; 1-Crotonoyl-2,6,6-trimethyl-1,3-cyclohexadiene; 2,6,6-Trimethyl-1-(2-butenoyl)-1,3-cyclohexadiene

C13H18O (190.1358)


Beta-damascenone is a cyclic monoterpene ketone that is 2,6,6-trimethylcyclohexa-1,3-diene substituted at position 1 by a crotonoyl group. It has a role as a fragrance, a volatile oil component and a plant metabolite. It is an enone, an apo carotenoid monoterpenoid and a cyclic monoterpene ketone. Damascenone is a natural product found in Vitis rotundifolia, Vitis labrusca, and other organisms with data available. 1-[2,6,6-Trimethyl-1,3-cyclohexadien-1-yl]-2-buten-1-one is a metabolite found in or produced by Saccharomyces cerevisiae. trans-beta-damascenone is a metabolite found in or produced by Saccharomyces cerevisiae. Damascenones are a series of closely related chemical compounds that are components of a variety of essential oils. The damascenones belong to a family of chemicals known as rose ketones, which also includes damascones and ionones. beta-Damascenone is a major contributor to the aroma of roses, despite its very low concentration, and is an important fragrance chemical used in perfumery. [Wikipedia] From Rosa damascena and many other sources. 3,5,8-Megastigmatrien-7-one is found in many foods, some of which are herbs and spices, tea, common grape, and green vegetables. A cyclic monoterpene ketone that is 2,6,6-trimethylcyclohexa-1,3-diene substituted at position 1 by a crotonoyl group. Damascenone ((E/Z)-Damascenone) is an active compound of?Epipremnum pinnatum with anti-inflammatory activity[1]. Damascenone is a mixture complex of?E-isomer-Damascenone and Z-isomer Damascenone. Damascenone ((E/Z)-Damascenone) is an active compound of?Epipremnum pinnatum with anti-inflammatory activity[1]. Damascenone is a mixture complex of?E-isomer-Damascenone and Z-isomer Damascenone.

   

Pentacosane

2A4605C9-A088-458C-AD58-AA987FF6C408

C25H52 (352.4069)


Constituent of many naturally occurring waxes. A colorless solid at ambient conditions. Pentacosane is an alkane consisting of an unbranched chain of 25 carbon atoms. It has a role as a semiochemical and a plant metabolite. Pentacosane is a natural product found in Cryptotermes brevis, Erucaria microcarpa, and other organisms with data available. See also: Moringa oleifera leaf oil (part of). An alkane consisting of an unbranched chain of 25 carbon atoms. Pentacosane is one of the major components in the acetone extract from Curcuma raktakanda and is also in the essential oil from the leaves of Malus domestica. Pentacosane exhibit anti-cancer activities[1]. Pentacosane is one of the major components in the acetone extract from Curcuma raktakanda and is also in the essential oil from the leaves of Malus domestica. Pentacosane exhibit anti-cancer activities[1].

   

Nonanal

Aldehyde C9, Nonyl aldehyde, Pelargonaldehyde

C9H18O (142.1358)


Nonanal, also known as nonyl aldehyde or pelargonaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, nonanal is considered to be a fatty aldehyde lipid molecule. Nonanal acts synergistically with carbon dioxide in that regard. Nonanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Nonanal exists in all eukaryotes, ranging from yeast to humans. Nonanal is an aldehydic, citrus, and fat tasting compound. nonanal is found, on average, in the highest concentration in a few different foods, such as corns, tea, and gingers and in a lower concentration in sweet oranges, carrots, and limes. nonanal has also been detected, but not quantified, in several different foods, such as olives, cereals and cereal products, chinese cinnamons, common grapes, and oats. This could make nonanal a potential biomarker for the consumption of these foods. Nonanal has been identified as a compound that attracts Culex mosquitoes. Nonanal is a potentially toxic compound. Nonanal has been found to be associated with several diseases such as pervasive developmental disorder not otherwise specified, autism, crohns disease, and ulcerative colitis; also nonanal has been linked to the inborn metabolic disorders including celiac disease. Nonanal, also called nonanaldehyde, pelargonaldehyde or Aldehyde C-9, is an alkyl aldehyde. Although it occurs in several natural oils, it is produced commercially by hydroformylation of 1-octene. A colourless, oily liquid, nonanal is a component of perfumes. Nonanal is a clear brown liquid characterized by a rose-orange odor. Insoluble in water. Found in at least 20 essential oils, including rose and citrus oils and several species of pine oil. Nonanal is a saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism. It has a role as a human metabolite and a plant metabolite. It is a saturated fatty aldehyde, a n-alkanal and a medium-chain fatty aldehyde. It is functionally related to a nonanoic acid. Nonanal is a natural product found in Teucrium montanum, Eupatorium cannabinum, and other organisms with data available. Nonanal is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.Nonanal belongs to the family of Medium-chain Aldehydes. These are An aldehyde with a chain length containing between 6 and 12 carbon atoms. Found in various plant sources including fresh fruits, citrus peels, cassava (Manihot esculenta), rice (Oryza sativa). Flavouring ingredient A saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism. Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1]. Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1].

   

Naringenin

5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

C15H12O5 (272.0685)


Naringenin is a trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 6 and 4. It is a trihydroxyflavanone and a member of 4-hydroxyflavanones. 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one is a natural product found in Prunus mume, Helichrysum cephaloideum, and other organisms with data available. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D004965 - Estrogen Antagonists A trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 6 and 4. D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

   

1-Hexanol

1-Hexanol, aluminum salt

C6H14O (102.1045)


1-Hexanol is an organic alcohol with a six carbon chain and a condensed structural formula of CH3(CH2)5OH. This colorless liquid is slightly soluble in water, but miscible with ether and ethanol. Two additional straight chain isomers of 1-hexanol exist, 2-hexanol and 3-hexanol, both of which differ by the location of the hydroxyl group. Many isomeric alcohols have the formula C6H13OH. 1-hexanol is believed to be a component of the odour of freshly mowed grass. It is used in the perfume industry and as a flavouring agent. 1-Hexanol is found in many foods, some of which are lemon, tea, yellow bell pepper, and hyssop. 1-Hexanol is a common constituent of essential oils (e.g. orange peel oil). 1-Hexanol is an organic alcohol with a six carbon chain and a condensed structural formula of CH3(CH2)5OH. This colorless liquid is slightly soluble in water, but miscible with ether and ethanol. Two additional straight chain isomers of 1-hexanol exist, 2-hexanol and 3-hexanol, both of which differ by the location of the hydroxyl group. Many isomeric alcohols have the formula C6H13OH. 1-hexanol is believed to be a component of the odour of freshly mown grass. It is used in the perfume industry. D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists

   

Hexyl acetate

1-Octanamine, hydrochloride

C8H16O2 (144.115)


Hexyl acetate, also known as N-hexyl ethanoate or hexyl acetic acid, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). The acetate ester of hexan-1-ol. Hexyl acetate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Hexyl acetate is a sweet, apple, and banana tasting compound. Hexyl acetate is found, on average, in the highest concentration within highbush blueberries. Hexyl acetate has also been detected, but not quantified, in several different foods, such as alcoholic beverages, pears, oats, roman camomiles, and sweet cherries. This could make hexyl acetate a potential biomarker for the consumption of these foods. Hexyl acetate is used in fruit essences and fruit aroma concentrates. It is found in wines, black tea, soya bean, roman camomile, peach, purple mangosteen, and muskmelon.

   

alpha-Curcumene

1-methyl-4-(6-methylhept-5-en-2-yl)benzene

C15H22 (202.1721)


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

   

Undecanal

Undecylic aldehyde

C11H22O (170.1671)


Undecanal, also known as undecyl aldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, undecanal is considered to be a fatty aldehyde lipid molecule. Undecanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Undecanal is a sweet, aldehydic, and citrus tasting compound. Undecanal is found, on average, in the highest concentration within corianders. Undecanal has also been detected, but not quantified, in several different foods, such as lemons, sweet basils, rocket salad (ssp.), corns, and citrus. This could make undecanal a potential biomarker for the consumption of these foods. Found in many essential oils, e.g. Citrus subspecies and oval kumquat Fortunella marginata. Found in many essential oils, e.g. Citrus subspecies and oval kumquat Fortunella marginata. Flavouring ingredient.

   

Tridecanal

N-Tridecylaldehyde

C13H26O (198.1984)


Volatile flavour component of coriander leafand is also in lemon and cucumber oils. Tridecanal is found in many foods, some of which are herbs and spices, lemon, corn, and citrus. Tridecanal is found in citrus. Tridecanal is a volatile flavour component of coriander leaf. Also in lemon and cucumber oil

   

8alpha,13R-Epoxy-14-labden-19-oic acid

3-ethenyl-3,4a,7,10a-tetramethyl-dodecahydro-1H-naphtho[2,1-b]pyran-7-carboxylic acid

C20H32O3 (320.2351)


8alpha,13R-Epoxy-14-labden-19-oic acid is isolated from Pinus sylvestris (Scotch pine). Isolated from Pinus sylvestris (Scotch pine)

   

xi-p-Menth-3-ene

4-methyl-1-(propan-2-yl)cyclohex-1-ene

C10H18 (138.1408)


xi-p-Menth-3-ene is found in herbs and spices. xi-p-Menth-3-ene is isolated from thyme and peppermint oil. Isolated from thyme and peppermint oil. xi-p-Menth-3-ene is found in herbs and spices.

   

3,7-Dimethylocta-2,6-dien-1-ol

3,7-dimethylocta-2,6-dien-1-ol

C10H18O (154.1358)


   

Hex-3-en-1-al

3-hexen-1-ol, (Z)-isomer

C6H12O (100.0888)


Cis-Hex-3-en-1-ol or (Z)-3-Hexen-1-ol, also known as (3Z)-hex-3-en-1-ol or leaf alcohol, 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. Thus, (Z)-3-hexen-1-ol is considered to be a fatty alcohol lipid molecule. (Z)-3-Hexen-1-ol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a colorless oily Liquid with an intense grassy-green odor of freshly cut green grass and leaves. Cis-Hex-3-en-1-ol is produced in small amounts by most plants and it acts as an attractant to many predatory insects. Cis-3-Hexen-1-ol is a very important aroma compound that is used in fruit and vegetable flavors and in perfumes. Hex-3-en-1-al, also known as 3-hexen-1-ol or cis-3-hexenol, is a member of the class of compounds known as fatty alcohols. Fatty alcohols are aliphatic alcohols consisting of a chain of a least six carbon atoms. Hex-3-en-1-al is soluble (in water) and an extremely weak acidic compound (based on its pKa). Hex-3-en-1-al can be found in burdock, which makes hex-3-en-1-al a potential biomarker for the consumption of this food product.

   

N-Pentacosane

CH3-[CH2]23-CH3

C25H52 (352.4069)


Pentacosane, also known as ch3-[ch2]23-ch3, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, pentacosane is considered to be a hydrocarbon lipid molecule. Pentacosane can be found in a number of food items such as ginkgo nuts, papaya, black elderberry, and cardamom, which makes pentacosane a potential biomarker for the consumption of these food products. The term higher alkanes is sometimes used literally as "alkanes with a higher number of carbon atoms". One definition distinguishes the higher alkanes as the n-alkanes that are solid under natural conditions . n-Pentacosane, also known as CH3-[CH2]23-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. n-pentacosane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. n-Pentacosane has been detected in coconuts, avocado, ginkgo nuts, cardamoms, and lindens. This could make n-pentacosane a potential biomarker for the consumption of these foods. Pentacosane is one of the major components in the acetone extract from Curcuma raktakanda and is also in the essential oil from the leaves of Malus domestica. Pentacosane exhibit anti-cancer activities[1]. Pentacosane is one of the major components in the acetone extract from Curcuma raktakanda and is also in the essential oil from the leaves of Malus domestica. Pentacosane exhibit anti-cancer activities[1].

   

Manool

5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-ol

C20H34O (290.261)


Manool, also known as (+)-manool, is a member of the class of compounds known as diterpenoids. Diterpenoids are terpene compounds formed by four isoprene units. Manool is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Manool can be found in common sage, which makes manool a potential biomarker for the consumption of this food product. Manool is a diterpene from Salvia officinalis. Manool induces selective cytotoxicity in cancer cells. Manool arrests the cancer cells at the G(2)/M phase of the cell cycle[1][2]. Manool is a diterpene from Salvia officinalis. Manool induces selective cytotoxicity in cancer cells. Manool arrests the cancer cells at the G(2)/M phase of the cell cycle[1][2].

   

D-Camphor

1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one

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].

   

Linoleate

cis-9, cis-12-octadecadienoic acid

C18H32O2 (280.2402)


COVID info from PDB, Protein Data Bank, WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

Oleate

cis-9-octadecenoic acid

C18H34O2 (282.2559)


COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

   

Sarcophytonolide E

Sarcophytonolide E

C20H32O3 (320.2351)


   

Palmitic Acid

n-Hexadecanoic acid

C16H32O2 (256.2402)


COVID info from WikiPathways D004791 - Enzyme Inhibitors Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

citrol

InChI=1\C10H18O\c1-9(2)5-4-6-10(3)7-8-11\h5,7,11H,4,6,8H2,1-3H3\b10-7

C10H18O (154.1358)


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].

   

bicyclogermacrene

bicyclogermacrene

C15H24 (204.1878)


A sesquiterpene derived from germacrane by dehydrogenation across the C(1)-C(10) and C(4)-C(5) bonds and cyclisation across the C(8)-C(9) bond.

   

methyl 4-methylazulene-1-carboxylate

methyl 4-methylazulene-1-carboxylate

C13H12O2 (200.0837)


   

Pentacosane

EINECS 211-123-6

C25H52 (352.4069)


Pentacosane is one of the major components in the acetone extract from Curcuma raktakanda and is also in the essential oil from the leaves of Malus domestica. Pentacosane exhibit anti-cancer activities[1]. Pentacosane is one of the major components in the acetone extract from Curcuma raktakanda and is also in the essential oil from the leaves of Malus domestica. Pentacosane exhibit anti-cancer activities[1].

   

Manool

(3R)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-ol

C20H34O (290.261)


A labdane diterpenoid in which the labdane skeleton has double bonds at positions 8(17) and 14 and carries an S-hydroxy group at position 13. Manool is a labdane diterpenoid in which the labdane skeleton has double bonds at positions 8(17) and 14 and carries an R-hydroxy group at position 13. It has a role as an antineoplastic agent, a plant metabolite and an antibacterial agent. It is a labdane diterpenoid and a tertiary alcohol. Manool is a natural product found in Halocarpus biformis, Cedrus atlantica, and other organisms with data available. A labdane diterpenoid in which the labdane skeleton has double bonds at positions 8(17) and 14 and carries an R-hydroxy group at position 13. Manool is a diterpene from Salvia officinalis. Manool induces selective cytotoxicity in cancer cells. Manool arrests the cancer cells at the G(2)/M phase of the cell cycle[1][2]. Manool is a diterpene from Salvia officinalis. Manool induces selective cytotoxicity in cancer cells. Manool arrests the cancer cells at the G(2)/M phase of the cell cycle[1][2].

   

Terpenol

3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, sodium salt, (1S)-

C10H18O (154.1358)


Alpha-terpineol is a terpineol that is propan-2-ol substituted by a 4-methylcyclohex-3-en-1-yl group at position 2. It has a role as a plant metabolite. alpha-TERPINEOL is a natural product found in Nepeta nepetella, Xylopia aromatica, and other organisms with data available. 2-(4-Methyl-3-cyclohexen-1-yl)-2-propanol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Coriander Oil (part of); Cannabis sativa subsp. indica top (part of); Peumus boldus leaf (part of). A terpineol that is propan-2-ol substituted by a 4-methylcyclohex-3-en-1-yl group at position 2. (-)-α-Terpineol ((S)-α-Terpineol), a monoterpene compound, is one of compounds in Melaleuca alternifolia[1]. (-)-α-Terpineol ((S)-α-Terpineol), a monoterpene compound, is one of compounds in Melaleuca alternifolia[1]. (-)-α-Terpineol ((S)-α-Terpineol), a monoterpene compound, is one of compounds in Melaleuca alternifolia[1]. (-)-α-Terpineol ((S)-α-Terpineol), a monoterpene compound, is one of compounds in Melaleuca alternifolia[1]. 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].

   

ferulate

InChI=1\C10H10O4\c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13\h2-6,11H,1H3,(H,12,13

C10H10O4 (194.0579)


Ferulic acid, also known as 4-hydroxy-3-methoxycinnamic acid or 3-methoxy-4-hydroxy-trans-cinnamic acid, is a member of the class of compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Ferulic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Ferulic acid can be found in a number of food items such as flaxseed, pepper (c. chinense), chinese cinnamon, and wakame, which makes ferulic acid a potential biomarker for the consumption of these food products. Ferulic acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts and stratum corneum tissues. Ferulic acid exists in all eukaryotes, ranging from yeast to humans. Ferulic acid is a hydroxycinnamic acid, a type of organic compound. It is an abundant phenolic phytochemical found in plant cell walls, covalently bonded as side chains to molecules such as arabinoxylans. As a component of lignin, ferulic acid is a precursor in the manufacture of other aromatic compounds. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis) . D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D002491 - Central Nervous System Agents > D000700 - Analgesics D000975 - Antioxidants > D016166 - Free Radical Scavengers D006401 - Hematologic Agents > D000925 - Anticoagulants D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively.

   

Ferulic acid

4-hydroxy-3-methoxycinnamic acid

C10H10O4 (194.0579)


(E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively.

   

Phytol

2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, (theta-(theta,theta-(E)))-

C20H40O (296.3079)


Phytol is a key acyclic diterpene alcohol that is a precursor for vitamins E and K1. Phytol is an extremely common terpenoid, found in all plants esterified to Chlorophyll to confer lipid solubility[citation needed].; Phytol is a natural linear diterpene alcohol which is used in the preparation of vitamins E and K1. It is also a decomposition product of chlorophyll. It is an oily liquid that is nearly insoluble in water, but soluble in most organic solvents. -- Wikipedia C1907 - Drug, Natural Product > C28269 - Phytochemical Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1]. Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1].

   

stearic acid

stearic acid

C18H36O2 (284.2715)


Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

   

Oleic acid

cis-9-Octadecenoic acid

C18H34O2 (282.2559)


An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry. Oleic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=112-80-1 (retrieved 2024-07-16) (CAS RN: 112-80-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent. Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

   

phenylacetaldehyde

phenylacetaldehyde

C8H8O (120.0575)


An aldehyde that consists of acetaldehyde bearing a methyl substituent; the parent member of the phenylacetaldehyde class of compounds. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

Decanal

4-01-00-03366 (Beilstein Handbook Reference)

C10H20O (156.1514)


A saturated fatty aldehyde formally arising from reduction of the carboxy group of capric acid (decanoic acid). Decyl aldehyde is a simple ten-carbon aldehyde. Decyl aldehyde is a bacterial luciferase substrate. Decyl aldehyde is a simple ten-carbon aldehyde. Decyl aldehyde is a bacterial luciferase substrate.

   

Octanal

InChI=1\C8H16O\c1-2-3-4-5-6-7-8-9\h8H,2-7H2,1H

C8H16O (128.1201)


A - Alimentary tract and metabolism > A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents Octanal is an aromatic aldehyde, with antioxidant and antimicrobial activities. Octanal shows cytotoxicity against Hela cells[1]. Octanal is an aromatic aldehyde, with antioxidant and antimicrobial activities. Octanal shows cytotoxicity against Hela cells[1].

   

Octanol

InChI=1\C8H18O\c1-2-3-4-5-6-7-8-9\h9H,2-8H2,1H

C8H18O (130.1358)


D012997 - Solvents 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2]. 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2].

   

FA 18:3

(-)-lamenallenic acid;(-)-octadeca-5,6-trans-16-trienoic acid

C18H30O2 (278.2246)


CONFIDENCE standard compound; INTERNAL_ID 143 COVID info from WikiPathways D - Dermatologicals Same as: D07213 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].

   

Hexadecanoic acid

Hexadecanoic acid

C16H32O2 (256.2402)


   

Octadecanoic acid

Octadecanoic acid

C18H36O2 (284.2715)


A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.

   

caryophyllene

(-)-beta-Caryophyllene

C15H24 (204.1878)


A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.

   

Nonanal

4-01-00-03352 (Beilstein Handbook Reference)

C9H18O (142.1358)


Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1]. Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1].

   

Hexalin

Hexyl alcohol (natural)

C6H14O (102.1045)


D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists

   

Hexyl acetate

Hexyl acetate

C8H16O2 (144.115)


The acetate ester of hexan-1-ol.

   

Asahina

4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)-

C15H12O5 (272.0685)


D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D004965 - Estrogen Antagonists D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

   

Stearol

Stearyl alcohol pure

C18H38O (270.2922)


1-Hydroxyoctadecane is an endogenous metabolite. 1-Hydroxyoctadecane is an endogenous metabolite.

   

UNDECANAL

UNDECANAL

C11H22O (170.1671)


A saturated fatty aldehyde formally arising from reduction of the carboxylic acid group of undecanoic acid. It is a component of essential oils from citrus plants like Citrus reticulata.

   

Tridecyl aldehyde

N-Tridecylaldehyde

C13H26O (198.1984)


A long-chain fatty aldehyde that is tridecane in which two hydrogens attached to a terminal carbon are replaced by an oxo group.

   

PENTADECANAL

PENTADECANAL

C15H30O (226.2297)


A long-chain fatty aldehyde that is pentadecane carrying an oxo substituent at position 1. It is a component of essential oils from plants like Solanum erianthum and Cassia siamea.

   

Damascenone

2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (2E)-

C13H18O (190.1358)


Damascenone ((E/Z)-Damascenone) is an active compound of?Epipremnum pinnatum with anti-inflammatory activity[1]. Damascenone is a mixture complex of?E-isomer-Damascenone and Z-isomer Damascenone. Damascenone ((E/Z)-Damascenone) is an active compound of?Epipremnum pinnatum with anti-inflammatory activity[1]. Damascenone is a mixture complex of?E-isomer-Damascenone and Z-isomer Damascenone.

   

8a,13R-Epoxy-14-labden-19-Oic acid

3-ethenyl-3,4a,7,10a-tetramethyl-dodecahydro-1H-naphtho[2,1-b]pyran-7-carboxylic acid

C20H32O3 (320.2351)


   

Copalic acid

(2Z)-5-(5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl)-3-methylpent-2-enoic acid

C20H32O2 (304.2402)


   

FOH 16:0

3S,7S-dimethyl-tetradecan-2S-ol

C16H34O (242.261)


1-Hexadecanol is a fatty alcohol, a lipophilic substrate. 1-Hexadecanol is a fatty alcohol, a lipophilic substrate.

   

FOH 18:0

3S,7S-dimethyl-hexadecan-2-ol

C18H38O (270.2922)


1-Hydroxyoctadecane is an endogenous metabolite. 1-Hydroxyoctadecane is an endogenous metabolite.

   

FOH 8:0

(2S)-2-octanol;(S)-(+)-2-octanol;(S)-2-octanol;d-octan-2-ol

C8H18O (130.1358)


D012997 - Solvents 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2]. 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2].

   

FAL 11:0

UNDECANAL

C11H22O (170.1671)


   

FAL 13:0

TRIDECANAL

C13H26O (198.1984)


   

FAL 15:0

13-methyltetradecanal

C15H30O (226.2297)


   

SFE 8:0

Propyl 3-methylbutanoate

C8H16O2 (144.115)


   

HENTRIACONTANE

HENTRIACONTANE

C31H64 (436.5008)


   

P-CYMENE

P-CYMENE

C10H14 (134.1095)


A monoterpene that is toluene substituted by an isopropyl group at position 4.

   

alpha-Curcumene

1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]benzene

C15H22 (202.1721)


Alpha-curcumene is also known as α-curcumene. Alpha-curcumene is a herb tasting compound and can be found in a number of food items such as pepper (spice), lovage, wild carrot, and rosemary, which makes alpha-curcumene a potential biomarker for the consumption of these food products.

   

naphthalene

naphthalene

C10H8 (128.0626)


An aromatic hydrocarbon comprising two fused benzene rings. It occurs in the essential oils of numerous plant species e.g. magnolia.

   

Cyclohexene, 4-methyl-1-(1-methylethyl)-

Cyclohexene, 4-methyl-1-(1-methylethyl)-

C10H18 (138.1408)


   

alpha-terpineol

alpha-terpineol

C10H18O (154.1358)


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].

   

Humulene

trans,trans,trans-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene

C15H24 (204.1878)


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].

   

Cymol

InChI=1\C10H14\c1-8(2)10-6-4-9(3)5-7-10\h4-8H,1-3H

C10H14 (134.1095)


   

α-Pinene

InChI=1\C10H16\c1-7-4-5-8-6-9(7)10(8,2)3\h4,8-9H,5-6H2,1-3H

C10H16 (136.1252)


A pinene that is bicyclo[3.1.1]hept-2-ene substituted by methyl groups at positions 2, 6 and 6 respectively. (-)-α-Pinene is a monoterpene and shows sleep enhancing property through a direct binding to GABAA-benzodiazepine (BZD) receptors by acting as a partial modulator at the BZD binding site[1]. (-)-α-Pinene is a monoterpene and shows sleep enhancing property through a direct binding to GABAA-benzodiazepine (BZD) receptors by acting as a partial modulator at the BZD binding site[1]. (-)-α-Pinene is a monoterpene and shows sleep enhancing property through a direct binding to GABAA-benzodiazepine (BZD) receptors by acting as a partial modulator at the BZD binding site[1]. (-)-α-Pinene is a monoterpene and shows sleep enhancing property through a direct binding to GABAA-benzodiazepine (BZD) receptors by acting as a partial modulator at the BZD binding site[1]. (-)-α-Pinene is a monoterpene and shows sleep enhancing property through a direct binding to GABAA-benzodiazepine (BZD) receptors by acting as a partial modulator at the BZD binding site[1]. (-)-α-Pinene is a monoterpene and shows sleep enhancing property through a direct binding to GABAA-benzodiazepine (BZD) receptors by acting as a partial modulator at the BZD binding site[1].

   

Cognac oil

9,12-Octadecadienoic acid, (Z,Z)-, labeled with carbon-14

C18H32O2 (280.2402)


An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry. COVID info from PDB, Protein Data Bank, WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

Nonacosane

EINECS 211-126-2

C29H60 (408.4695)


Nonacosane, isolated from Baphia massaiensis, exhibits weak activities against E. coli, B. subtilis, P. aeruginosa and S. aureus[1]. Nonacosane, isolated from Baphia massaiensis, exhibits weak activities against E. coli, B. subtilis, P. aeruginosa and S. aureus[1].

   

Hexanol

4-01-00-01694 (Beilstein Handbook Reference)

C6H14O (102.1045)


D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists

   

Red oil

4-02-00-01641 (Beilstein Handbook Reference)

C18H34O2 (282.2559)


COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

   

Hyacinthin

InChI=1\C8H8O\c9-7-6-8-4-2-1-3-5-8\h1-5,7H,6H

C8H8O (120.0575)


COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

linoleic

9,12-Octadecadienoic acid, (9E,12E)-

C18H32O2 (280.2402)


Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1]. Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1].

   

Hypnon

InChI=1\C8H8O\c1-7(9)8-5-3-2-4-6-8\h2-6H,1H

C8H8O (120.0575)


D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents D003879 - Dermatologic Agents Acetophenone is an organic compound with simple structure[1]. Acetophenone is an organic compound with simple structure[1].

   

Dodecanal

InChI=1\C12H24O\c1-2-3-4-5-6-7-8-9-10-11-12-13\h12H,2-11H2,1H

C12H24O (184.1827)


   

Hentriacontan

N-Hentriacontane

C31H64 (436.5008)


   

Naftalen

Naphthalene, crude or refined [UN1334] [Flammable solid]

C10H8 (128.0626)


   

Polaax

InChI=1\C18H38O\c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19\h19H,2-18H2,1H

C18H38O (270.2922)


1-Hydroxyoctadecane is an endogenous metabolite. 1-Hydroxyoctadecane is an endogenous metabolite.

   

Ethol

InChI=1\C16H34O\c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17\h17H,2-16H2,1H

C16H34O (242.261)


1-Hexadecanol is a fatty alcohol, a lipophilic substrate. 1-Hexadecanol is a fatty alcohol, a lipophilic substrate.

   

Hendecenal

Aldehyde C-11, undecylic

C11H22O (170.1671)


   

CHEBI:17302

EINECS 220-435-1

C15H30O (226.2297)


   

WLN: 6OV1

4-02-00-00159 (Beilstein Handbook Reference)

C8H16O2 (144.115)


   

epoxide

[1R-(1R*,4R*,6R*,10S*)]- Caryophylene oxide Caryophyllene epoxide Caryophyllene oxyde Epoxycaryophyllene [1R-(1R*,4R*,6R*,10S*)]-4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane <>-Caryophyllene epoxide <>-Caryophyllene 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). A natural product found in Cupania cinerea. 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].

   

1-octanol

1-octanol

C8H18O (130.1358)


D012997 - Solvents 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2]. 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2].

   

Cetyl alcohol

Hexadecan-1-ol

C16H34O (242.261)


A long-chain primary fatty alcohol that is hexadecane substituted by a hydroxy group at position 1. 1-Hexadecanol is a fatty alcohol, a lipophilic substrate. 1-Hexadecanol is a fatty alcohol, a lipophilic substrate.

   

1-Hexanol

1-Hexanol

C6H14O (102.1045)


D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists

   

(9Z)-octadec-9-en-12-ynoic acid

(9Z)-octadec-9-en-12-ynoic acid

C18H30O2 (278.2246)


An octadecenynoic acid having a cis-double bond at C-9 and a triple bond at position 12.

   

5-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-3-{[(2-methylbutanoyl)oxy]methyl}pent-2-enoic acid

5-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-3-{[(2-methylbutanoyl)oxy]methyl}pent-2-enoic acid

C25H40O4 (404.2926)


   

4-{2-[(1r,4ar,7r,8ar)-7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]ethyl}-5h-furan-2-one

4-{2-[(1r,4ar,7r,8ar)-7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]ethyl}-5h-furan-2-one

C20H30O3 (318.2195)


   

(2z)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

(2z)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

C22H34O4 (362.2457)


   

(2e)-5-[(1r,4r,4ar,8as)-4-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid

(2e)-5-[(1r,4r,4ar,8as)-4-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid

C20H32O3 (320.2351)


   

5-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid

5-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid

C20H32O2 (304.2402)


   

4-({8-[5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl}oxy)-4-oxobutanoic acid

4-({8-[5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl}oxy)-4-oxobutanoic acid

C26H40O6 (448.2825)


   

3-[(acetyloxy)methyl]-5-[5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]pent-2-enoic acid

3-[(acetyloxy)methyl]-5-[5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]pent-2-enoic acid

C22H34O5 (378.2406)


   

5-(4-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid

5-(4-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid

C20H32O3 (320.2351)


   

3-[(acetyloxy)methyl]-5-(4-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)pent-2-enoic acid

3-[(acetyloxy)methyl]-5-(4-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)pent-2-enoic acid

C22H34O5 (378.2406)


   

(2e)-5-[(1r,4ar,7r,8ar)-7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid

(2e)-5-[(1r,4ar,7r,8ar)-7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid

C20H32O3 (320.2351)


   

(2e)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid

(2e)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid

C20H32O2 (304.2402)


   

5-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-3-{[(2-methylpropanoyl)oxy]methyl}pent-2-enoic acid

5-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-3-{[(2-methylpropanoyl)oxy]methyl}pent-2-enoic acid

C24H38O4 (390.277)


   

5-[(2r)-2-(4-methylphenyl)propyl]furan-3-carbaldehyde

5-[(2r)-2-(4-methylphenyl)propyl]furan-3-carbaldehyde

C15H16O2 (228.115)


   

5-[2-(4-methylphenyl)propyl]furan-3-carbaldehyde

5-[2-(4-methylphenyl)propyl]furan-3-carbaldehyde

C15H16O2 (228.115)


   

(1s,2r)-2-[(3e,7s)-7-hydroxy-3,7-dimethylnona-3,8-dien-1-yl]-1,3,3-trimethylcyclohexan-1-ol

(1s,2r)-2-[(3e,7s)-7-hydroxy-3,7-dimethylnona-3,8-dien-1-yl]-1,3,3-trimethylcyclohexan-1-ol

C20H36O2 (308.2715)


   

(2z)-5-[(1r,4as,5r,8as)-5-[(acetyloxy)methyl]-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

(2z)-5-[(1r,4as,5r,8as)-5-[(acetyloxy)methyl]-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

C24H36O6 (420.2512)


   

4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid

4-{[(2r,4ar,8r,8ar)-8-[(3e)-5-(acetyloxy)-3-methylpent-3-en-1-yl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-yl]oxy}-4-oxobutanoic acid

C26H40O6 (448.2825)


   

4-({3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-yl}methoxy)-4-oxobutanoic acid

4-({3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-yl}methoxy)-4-oxobutanoic acid

C24H38O5 (406.2719)


   

2-(7-hydroxy-3,7-dimethylnona-3,8-dien-1-yl)-1,3,3-trimethylcyclohexan-1-ol

2-(7-hydroxy-3,7-dimethylnona-3,8-dien-1-yl)-1,3,3-trimethylcyclohexan-1-ol

C20H36O2 (308.2715)


   

4-{2-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]ethyl}-5h-furan-2-one

4-{2-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]ethyl}-5h-furan-2-one

C20H30O2 (302.2246)


   

(2z)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-{[(2-methylpropanoyl)oxy]methyl}pent-2-enoic acid

(2z)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-{[(2-methylpropanoyl)oxy]methyl}pent-2-enoic acid

C24H38O4 (390.277)


   

4-{2-[(1r,4ar,7r,8ar)-7-methoxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]ethyl}-5h-furan-2-one

4-{2-[(1r,4ar,7r,8ar)-7-methoxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]ethyl}-5h-furan-2-one

C21H32O3 (332.2351)


   

(2e)-5-[(1r,4as,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid

(2e)-5-[(1r,4as,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid

C20H32O3 (320.2351)


   

4-{[9-(2,2-dimethyl-6-methylidenecyclohexyl)-3-hydroxy-3,7-dimethylnona-1,6-dien-5-yl]oxy}-4-oxobutanoic acid

4-{[9-(2,2-dimethyl-6-methylidenecyclohexyl)-3-hydroxy-3,7-dimethylnona-1,6-dien-5-yl]oxy}-4-oxobutanoic acid

C24H38O5 (406.2719)


   

(2e)-5-[(1r,4as,5r,8as)-5-[(acetyloxy)methyl]-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

(2e)-5-[(1r,4as,5r,8as)-5-[(acetyloxy)methyl]-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

C24H36O6 (420.2512)


   

5-hydroxy-4-[2-(7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)ethyl]-5h-furan-2-one

5-hydroxy-4-[2-(7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)ethyl]-5h-furan-2-one

C20H30O4 (334.2144)


   

5-(7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid

5-(7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid

C20H32O3 (320.2351)


   

(2z)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-7-oxo-hexahydronaphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

(2z)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-7-oxo-hexahydronaphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

C22H32O5 (376.225)


   

(3r,4as,6as,7r,10ar,10bs)-3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-carboxylic acid

(3r,4as,6as,7r,10ar,10bs)-3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-carboxylic acid

C20H32O3 (320.2351)


   

methyl 4-formylazulene-1-carboxylate

methyl 4-formylazulene-1-carboxylate

C13H10O3 (214.063)


   

(2e)-5-[(1r,4ar,7r,8ar)-7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

(2e)-5-[(1r,4ar,7r,8ar)-7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

C22H34O5 (378.2406)


   

(5s)-4-{2-[(1r,4ar,7r,8ar)-7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]ethyl}-5-hydroxy-5h-furan-2-one

(5s)-4-{2-[(1r,4ar,7r,8ar)-7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]ethyl}-5-hydroxy-5h-furan-2-one

C20H30O4 (334.2144)


   

[(1r,4as,5r,8as)-1,4a-dimethyl-6-methylidene-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-1-yl]methyl acetate

[(1r,4as,5r,8as)-1,4a-dimethyl-6-methylidene-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-1-yl]methyl acetate

C22H32O4 (360.23)


   

(3s,4as,6as,7r,10ar,10bs)-3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-carboxylic acid

(3s,4as,6as,7r,10ar,10bs)-3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-carboxylic acid

C20H32O3 (320.2351)


   

4-[2-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)ethyl]-5-hydroxy-5h-furan-2-one

4-[2-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)ethyl]-5-hydroxy-5h-furan-2-one

C20H30O3 (318.2195)


   

(2z)-5-[(1r,4as,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

(2z)-5-[(1r,4as,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

C22H34O5 (378.2406)


   

5-{5-[(acetyloxy)methyl]-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl}-3-methylpent-2-enoic acid

5-{5-[(acetyloxy)methyl]-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl}-3-methylpent-2-enoic acid

C22H34O4 (362.2457)


   

(5r)-4-{2-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]ethyl}-5-hydroxy-5h-furan-2-one

(5r)-4-{2-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]ethyl}-5-hydroxy-5h-furan-2-one

C20H30O3 (318.2195)


   

5-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-4-(acetyloxy)-3-methylpent-2-enoic acid

5-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-4-(acetyloxy)-3-methylpent-2-enoic acid

C22H34O4 (362.2457)


   

4-[2-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)ethyl]-5h-furan-2-one

4-[2-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)ethyl]-5h-furan-2-one

C20H30O2 (302.2246)


   

{1,4a-dimethyl-6-methylidene-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-1-yl}methyl acetate

{1,4a-dimethyl-6-methylidene-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-1-yl}methyl acetate

C22H32O4 (360.23)


   

4-{[(3s,5s,6e)-9-[(1r)-2,2-dimethyl-6-methylidenecyclohexyl]-3-hydroxy-3,7-dimethylnona-1,6-dien-5-yl]oxy}-4-oxobutanoic acid

4-{[(3s,5s,6e)-9-[(1r)-2,2-dimethyl-6-methylidenecyclohexyl]-3-hydroxy-3,7-dimethylnona-1,6-dien-5-yl]oxy}-4-oxobutanoic acid

C24H38O5 (406.2719)


   

4-[2-(7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)ethyl]-5h-furan-2-one

4-[2-(7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)ethyl]-5h-furan-2-one

C20H30O3 (318.2195)


   

5-(5,5,8a-trimethyl-2-methylidene-7-oxo-hexahydronaphthalen-1-yl)-3-[(acetyloxy)methyl]pent-2-enoic acid

5-(5,5,8a-trimethyl-2-methylidene-7-oxo-hexahydronaphthalen-1-yl)-3-[(acetyloxy)methyl]pent-2-enoic acid

C22H32O5 (376.225)


   

tridec-11-en-1,3,5,7,9-pentayne

tridec-11-en-1,3,5,7,9-pentayne

C13H6 (162.0469)


   

(2z)-5-[(1r,4ar,7r,8ar)-7-methoxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

(2z)-5-[(1r,4ar,7r,8ar)-7-methoxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

C23H36O5 (392.2563)


   

5-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-3-[(acetyloxy)methyl]pent-2-enoic acid

5-(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)-3-[(acetyloxy)methyl]pent-2-enoic acid

C22H34O4 (362.2457)


   

3-[(acetyloxy)methyl]-5-(7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)pent-2-enoic acid

3-[(acetyloxy)methyl]-5-(7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)pent-2-enoic acid

C22H34O5 (378.2406)


   

(2e)-5-[(1r,4as,5r,8as)-5-[(acetyloxy)methyl]-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid

(2e)-5-[(1r,4as,5r,8as)-5-[(acetyloxy)methyl]-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid

C22H34O4 (362.2457)


   

4-[2-(7-methoxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)ethyl]-5h-furan-2-one

4-[2-(7-methoxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)ethyl]-5h-furan-2-one

C21H32O3 (332.2351)


   

3-[(acetyloxy)methyl]-5-(7-methoxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)pent-2-enoic acid

3-[(acetyloxy)methyl]-5-(7-methoxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)pent-2-enoic acid

C23H36O5 (392.2563)


   

(2e,4s)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-4-(acetyloxy)-3-methylpent-2-enoic acid

(2e,4s)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-4-(acetyloxy)-3-methylpent-2-enoic acid

C22H34O4 (362.2457)


   

(2z)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-({[(2r)-2-methylbutanoyl]oxy}methyl)pent-2-enoic acid

(2z)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-({[(2r)-2-methylbutanoyl]oxy}methyl)pent-2-enoic acid

C25H40O4 (404.2926)


   

(2z)-5-[(1r,4r,4ar,8as)-4-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

(2z)-5-[(1r,4r,4ar,8as)-4-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

C22H34O5 (378.2406)


   

3-[(acetyloxy)methyl]-5-{5-[(acetyloxy)methyl]-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl}pent-2-enoic acid

3-[(acetyloxy)methyl]-5-{5-[(acetyloxy)methyl]-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl}pent-2-enoic acid

C24H36O6 (420.2512)


   

4-{[(3r,4as,6as,7r,10ar,10bs)-3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-yl]methoxy}-4-oxobutanoic acid

4-{[(3r,4as,6as,7r,10ar,10bs)-3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-yl]methoxy}-4-oxobutanoic acid

C24H38O5 (406.2719)


   

(2z)-5-[(1r,4ar,7r,8ar)-7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

(2z)-5-[(1r,4ar,7r,8ar)-7-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-[(acetyloxy)methyl]pent-2-enoic acid

C22H34O5 (378.2406)


   

4-{[(3s,4as,6as,7r,10ar,10bs)-3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-yl]methoxy}-4-oxobutanoic acid

4-{[(3s,4as,6as,7r,10ar,10bs)-3-ethenyl-3,4a,7,10a-tetramethyl-octahydro-1h-naphtho[2,1-b]pyran-7-yl]methoxy}-4-oxobutanoic acid

C24H38O5 (406.2719)


   

5-[5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid

5-[5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid

C20H32O3 (320.2351)