Classification Term: 1581

Menthane monoterpenoids (ontology term: CHEMONTID:0001401)

Monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes." [ISBN:9780412466205]

found 228 associated metabolites at category metabolite taxonomy ontology rank level.

Ancestor: Monoterpenoids

Child Taxonomies: There is no child term of current ontology term.

Menthol

(-)-Menthol, puriss., meets analytical specification of Ph. Eur., BP, USP, 98.0-102.0\\%

C10H20O (156.151407)


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

   

Perillyl alcohol

(S)-p-Mentha-1,8-dien-7-ol, (S)-4-Isopropenyl-1-cyclohexenylmethanol

C10H16O (152.12010859999998)


Perillyl alcohol is a monoterpene isolated from the essential oils of lavendin, peppermint, spearmint, cherries, celery seeds, and several other plants. In animal studies it has been shown to regress pancreatic, mammary, and liver tumors, to exhibit possible application as a chemopreventative agent for colon, skin, and lung cancer, and as a chemotherapeutic agent for neuroblastoma, and prostate and colon cancer.(PMID: 9855569) [HMDB]. p-Mentha-1,8-dien-7-ol is found in many foods, some of which are caraway, ginger, german camomile, and sweet bay. (S)-(-)-perillyl alcohol is a perillyl alcohol in which the chiral centre has S configuration. It is an enantiomer of a (R)-(+)-perillyl alcohol. Perillyl alcohol is under investigation in clinical trial NCT02704858 (Safety and Efficacy Study in Recurrent Grade IV Glioma). (-)-Perillyl alcohol is a natural product found in Teucrium pestalozzae, Canella winterana, and other organisms with data available. See also: Paeonia lactiflora root (part of). Perillyl alcohol is a monoterpene isolated from the essential oils of lavendin, peppermint, spearmint, cherries, celery seeds, and several other plants. In animal studies it has been shown to regress pancreatic, mammary, and liver tumors, to exhibit possible application as a chemopreventative agent for colon, skin, and lung cancer, and as a chemotherapeutic agent for neuroblastoma, and prostate and colon cancer.(PMID:9855569). C471 - Enzyme Inhibitor > C2020 - Farnesyl Transferase Inhibitor D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors (S)-(?)-Perillyl alcohol is a monoterpene found in lavender, inhibits farnesylation of Ras, upregulates the mannose-6-phosphate receptor and induces apoptosis. Anti-cancer activity[1]. (S)-(?)-Perillyl alcohol is a monoterpene found in lavender, inhibits farnesylation of Ras, upregulates the mannose-6-phosphate receptor and induces apoptosis. Anti-cancer activity[1]. Perillyl alcohol, a monoterpene,?is active in inducing apoptosis in tumor cells without affecting normal cells[1]. Perillyl alcohol, a monoterpene,?is active in inducing apoptosis in tumor cells without affecting normal cells[1].

   

Polylimonene

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

C10H16 (136.1251936)


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

   

(-)-Menthone

InChI=1/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s

C10H18O (154.1357578)


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

   

beta-Phellandrene

3-methylidene-6-(propan-2-yl)cyclohex-1-ene

C10H16 (136.1251936)


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

   

(R)-alpha-Phellandrene

(R)-(-)-alpha-Phellandrene, >=95.0\\% (sum of enantiomers, GC)

C10H16 (136.1251936)


(R)-alpha-Phellandrene is found in herbs and spices. (R)-alpha-Phellandrene is a constituent of oils of pimento, bay, Citrus, Juniperus, Mentha, and other essential oils. Oil of Zanthoxylum alatum is a major source (50\\%). (R)-alpha-Phellandrene is a flavouring agent.Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (Wikipedia) (-)-alpha-phellandrene is the (R)-(-)-stereoisomer of alpha-phellandrene. It is an enantiomer of a (+)-alpha-phellandrene. (R)-(-)-alpha-Phellandrene is a natural product found in Curcuma amada, Psidium guajava, and other organisms with data available. See also: Eucalyptus Oil (part of). Constituent of oils of pimento, bay, Citrus, Juniperus, Mentha, and other essential oils. Oil of Zanthoxylum alatum is a major source (50\\%). Flavouring agent The (R)-(-)-stereoisomer of alpha-phellandrene.

   

p-Menth-1-en-4-ol

Terpinen 4-ol, primary pharmaceutical reference standard

C10H18O (154.1357578)


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

   

(R)-Carvone

2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (theta)-

C10H14O (150.1044594)


Carvone, with R and S isomers, also known as carvol or limonen-6-one, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Carvone is a neutral compound. Carvone is a naturally occurring organic compound found in many essential oils but is most abundant in the oils from caraway seeds (Carum carvi), spearmint (Mentha spicata), and dill (PMID:27427817). Carvone is a volatile terpenoid found in cannabis plants (PMID:6991645 ). Carvone is occasionally found as a component of biological fluids in normal individuals. Both carvones (R, S) are used in the food and flavor industry (http//doi:10.1016/j.foodchem.2005.01.003). R-carvone is also used in air freshening products and in essential oils used in aromatherapy and alternative medicine. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841 (PMID:5556886 , 2477620 ). Carvone may help in the management of diseases (PMID:30374904) and had been considered as an adjuvant for treatment of cancer patients (PMID:30087792) and patients with epilepsy (PMID:31239862). It also has been successfully used as a biopesticide (PMID:30250476). (-)-carvone is a carvone having (R) configuration. It is an enantiomer of a (+)-carvone. (-)-Carvone is a natural product found in Poiretia latifolia, Licaria triandra, and other organisms with data available. See also: Myrrh (part of); Spearmint Oil (part of). Constituent of spearmint (Mentha crispa) costmary, kuromoji and other oils. Flavouring ingredient A carvone having (R) configuration. (-)-Carvone is an insect neurotoxin and a irreversible acetylcholinesterase (AChE) inhibitor. (-)-Carvone can be used as a bird repellent, inhibits larval growth, decreases pupatation rate, and increases mortality of larvae[1][2]. (-)-Carvone is an insect neurotoxin and a irreversible acetylcholinesterase (AChE) inhibitor. (-)-Carvone can be used as a bird repellent, inhibits larval growth, decreases pupatation rate, and increases mortality of larvae[1][2]. (-)-Carvone is an insect neurotoxin and a irreversible acetylcholinesterase (AChE) inhibitor. (-)-Carvone can be used as a bird repellent, inhibits larval growth, decreases pupatation rate, and increases mortality of larvae[1][2]. (-)-Carvone is an insect neurotoxin and a irreversible acetylcholinesterase (AChE) inhibitor. (-)-Carvone can be used as a bird repellent, inhibits larval growth, decreases pupatation rate, and increases mortality of larvae[1][2].

   

alpha-Terpinene

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

C10H16 (136.1251936)


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

   

(-)-Limonene

(S)-(-)-Limonene, purum, >=95.0\\% (sum of enantiomers, GC)

C10H16 (136.1251936)


Limonene is a monoterpene with a clear colourless liquid at room temperature, a naturally occurring chemical which is the major component in oil of oranges. Limonene is widely used as a flavour and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration (21 CFR 182.60 in the Code of Federal Regulations, U.S.A.). Limonene is a botanical (plant-derived) solvent of low toxicity. Mild skin irritation may occur from exposure to limonene and oxidation products of limonene may produce dermal sensitization, and may have irritative and bronchoconstrictive airway effects; however, data are scant and more studies are required. Limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Furthermore, chronic exposure to limonene causes a significant incidence of renal tubular tumours exclusively in male rats. Limonene is one of the active components of dietary phytochemicals that appears to be protective against cancer (PMID:16563357, 15499193, 15325315, 2024047). (4S)-limonene is an optically active form of limonene having (4S)-configuration. It is an enantiomer of a (4R)-limonene. (-)-Limonene is a natural product found in Poiretia latifolia, Kippistia suaedifolia, and other organisms with data available. 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: Spearmint Oil (part of). An optically active form of limonene having (4S)-configuration. (-)-Limonene ((S)-(-)-Limonene) is a monoterpene found in citrus plants like lemon, orange, and grape. (-)-Limonene can induce a mild bronchoconstrictive effect[1]. (-)-Limonene ((S)-(-)-Limonene) is a monoterpene found in citrus plants like lemon, orange, and grape. (-)-Limonene can induce a mild bronchoconstrictive effect[1]. (-)-Limonene ((S)-(-)-Limonene) is a monoterpene found in citrus plants like lemon, orange, and grape. (-)-Limonene can induce a mild bronchoconstrictive effect[1]. (-)-Limonene ((S)-(-)-Limonene) is a monoterpene found in citrus plants like lemon, orange, and grape. (-)-Limonene can induce a mild bronchoconstrictive effect[1].

   

Perillic acid

4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acid

C10H14O2 (166.09937440000002)


Perillic acid, also known as perillate, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Perillic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Perillic acid is an intermediate in the Limonene and pinene degradation pathway. (KEGG); Its measurement in urine is used to monitor cancer patients receiving oral Limonene (a farnesyl transferase inhibitor that has shown antitumor properties)(PubMed ID 8723738 ). Perillic acid is found in cardamom. C471 - Enzyme Inhibitor > C2020 - Farnesyl Transferase Inhibitor

   

(-)-trans-Carveol

(1S-trans)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-ol

C10H16O (152.12010859999998)


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

   

Terpinolene

1-methyl-4-(propan-2-ylidene)cyclohexene p-mentha-1,4(8)-diene

C10H16 (136.1251936)


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

   

Piperitenone

3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one, 9ci

C10H14O (150.1044594)


Piperitenone is a flavouring agent. It is found in grapefruit juice lemon juice, orange juice, spearmint oil and peppermint oil. It is also found in rosemary, mentha (mint), cornmint, and other herbs and spices. Piperitenone is found in citrus. Piperitenone is a flavouring agent. Piperitenone is present in grapefruit juice lemon juice, orange juice, spearmint oil and peppermint oi

   

Perillyl aldehyde

4-(1-Methylethenyl)-1-cyclohexene1-carboxyaldehyde

C10H14O (150.1044594)


(s)-perillaldehyde, also known as P-mentha-1,8-dien-7-al, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (s)-perillaldehyde is considered to be an isoprenoid lipid molecule (s)-perillaldehyde is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (s)-perillaldehyde is a cherry, fat, and fatty tasting compound found in herbs and spices, which makes (s)-perillaldehyde a potential biomarker for the consumption of this food product (s)-perillaldehyde can be found primarily in saliva. Perillaldehyde, or perilla aldehyde, is a natural organic compound found most abundantly in the perennial herb perilla, but also in a wide variety of other plants and essential oils. It is a monoterpenoid containing an aldehyde functional group.

   

p-Menthane-3,8-diol

(1R,2R,5R)-2-(1-hydroxy-1-methylethyl)-5-methylcyclohexanol;(1R,3R,4R)-2-hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol;(1R,3R,4R)-p-menthane-3,8-diol

C10H20O2 (172.14632200000003)


p-Menthane-3,8-diol is found in fruits. p-Menthane-3,8-diol is a constituent of the roots of Litsea cubeba (mountain pepper).p-Menthane-3,8-diol, also known as para-menthane-3,8-diol and PMD, is an active ingredient used in insect repellents. It smells similar to menthol and acts as a coolant. PMD is found in the oil within leaves of the Eucalyptus citriodora tree. This tree is native to Australia, but is now cultivated in many warm places around the world. This oil, when refined for use in insect repellents, is known as Oil of Lemon Eucalyptus or, more commonly, Citriodiol. Typically, Citriodiol contains 64\\% PMD (a mixture of the cis and trans isomers of p-menthane-3,8-diol). Citriodiol has been notified under the European Biocidal Products Directive (BPD) 98/8/EC and is currently proceeding through the registration process with the Heath and Safety Executive in the UK. It is the only natural ingredient that can now be used as an insect repellent D019141 - Respiratory System Agents > D005100 - Expectorants Constituent of the roots of Litsea cubeba (mountain pepper)

   

Piperitol

3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-ol, 9ci

C10H18O (154.1357578)


Flavouring material with a pungent taste. p-Menth-1-en-3-ol is found in dill, cumin, and spearmint. Piperitol is found in cumin. Piperitol is a flavouring material with a pungent tast

   

(+/-)-2-Hydroxypiperitone

2-hydroxy-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one

C10H16O2 (168.1150236)


(+/-)-2-hydroxypiperitone, also known as 2-hydroxy-6-isopropyl-3-methyl-2-cyclohexen-1-one or barosma camphor, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (+/-)-2-hydroxypiperitone is considered to be an isoprenoid lipid molecule (+/-)-2-hydroxypiperitone is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (+/-)-2-hydroxypiperitone is a blackcurrant, buchu, and leaves tasting compound found in blackcurrant, peppermint, and spearmint, which makes (+/-)-2-hydroxypiperitone a potential biomarker for the consumption of these food products.

   

(±)-Menthyl acetate

(1S,2R,5S)-5-Methyl-2-(propan-2-yl)cyclohexyl acetic acid

C12H22O2 (198.1619712)


(±)-menthyl acetate, also known as dl-P-menth-3-yl acetate, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (±)-menthyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (±)-menthyl acetate can be found in cornmint, which makes (±)-menthyl acetate a potential biomarker for the consumption of this food product. (±)-Menthyl acetate is found in cornmint. (±)-Menthyl acetate is a component of peppermint oil. ?Menthyl acetate (L-Menthyl acetate) is a derivative of L-menthol. ?Menthyl acetate is effective to enhance 5-aminolevulinic acid (ALA) skin permeation[1]. ?Menthyl acetate (L-Menthyl acetate) is a derivative of L-menthol. ?Menthyl acetate is effective to enhance 5-aminolevulinic acid (ALA) skin permeation[1].

   

(+)-beta-Phellandrene

(6R)-3-methylidene-6-(propan-2-yl)cyclohex-1-ene

C10H16 (136.1251936)


(+)-beta-Phellandrene is found in ginger. Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (Wikipedia). Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (+)-beta-Phellandrene is found in ginger.

   

(R)-Piperitone

(6R)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one

C10H16O (152.12010859999998)


(R)-Piperitone is found in cornmint. (R)-Piperitone is a constituent of Mentha species and Zanthoxylum piperitum (Japanese pepper tree) oil.Piperitone is a natural monoterpene ketone which is a component of some essential oils. Both stereoisomers, the D-form and the L-form, are known. The D-form has a peppermint-like aroma and has been isolated from the oils of plants from the genera Cymbopogon, Andropogon, and Mentha. The L-form has been isolated from Sitka spruce. (Wikipedia) Common constituent of Mentha subspecies oils

   

alpha-Terpineol

2-(4-Methylcyclohex-3-enyl)propan-2-ol (alpha-terpineol)

C10H18O (154.1357578)


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].

   

(-)-Dihydrocarveol

(1R,2R,5R)-2-Methyl-5-(prop-1-en-2-yl)cyclohexanol

C10H18O (154.1357578)


p-Menth-8-en-2-ol is found in herbs and spices. p-Menth-8-en-2-ol occurs in Mentha species, Piper longum (long pepper), Heracleum candicans and other essential oils. Stereoisomeric mixture used as flavour ingredien Occurs in Mentha subspecies, Piper longum (long pepper), Heracleum candicans and other essential oils. Stereoisomeric mixture used as flavour ingredient. p-Menth-8-en-2-ol is found in herbs and spices.

   

D-(+)-dihydrocarvone

(2R-trans)-2-Methyl-5-(1-methylvinyl)cyclohexan-1-one

C10H16O (152.12010859999998)


(1r,4r)-dihydrocarvone, also known as (2r,5r)-2-methyl-5-isopropenylcyclohexanone, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (1r,4r)-dihydrocarvone is considered to be an isoprenoid lipid molecule (1r,4r)-dihydrocarvone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (1r,4r)-dihydrocarvone is a herbal and minty tasting compound found in spearmint, which makes (1r,4r)-dihydrocarvone a potential biomarker for the consumption of this food product.

   

(-)-trans-Isopulegone

(2R-trans)-5-methyl-2-(1-methylethenyl)-cyclohexanone

C10H16O (152.12010859999998)


(-)-trans-Isopulegone is found in fats and oils. (-)-trans-Isopulegone is a flavouring ingredient. It is isolated from oil of American pennyroyal (Hedeoma pulegioides), Mentha species and others, usually with Pulegon Flavouring ingredient. Isolated from oil of American pennyroyal (Hedeoma pulegioides), Mentha subspecies and others, usually with Pulegone. (-)-trans-Isopulegone is found in fats and oils.

   

alpha-Terpineol acetate

2-(4-methylcyclohex-3-en-1-yl)propan-2-yl acetate

C12H20O2 (196.14632200000003)


alpha-Terpineol acetate, also known as a-terpineol acetic acid or p-menth-1-en-8-yl acetate, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. alpha-Terpineol acetate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. α-Terpinyl acetate is a monoterpene ester isolated from Laurus nobilis L. essential oil. α-Terpinyl acetate is a competitive P450 2B6 substrate which binding to the active site of P450 2B6 with a Kd value of 5.4?μM[1][2]. α-Terpinyl acetate is a monoterpene ester isolated from Laurus nobilis L. essential oil. α-Terpinyl acetate is a competitive P450 2B6 substrate which binding to the active site of P450 2B6 with a Kd value of 5.4?μM[1][2].

   

beta-Terpineol

(1r,4r)-1-methyl-4-(prop-1-en-2-yl)cyclohexan-1-ol

C10H18O (154.1357578)


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

   

gamma-Terpineol

1-Methyl-4-(1-methylethylidene)cyclohexanol, 9ci

C10H18O (154.1357578)


gamma-Terpineol is found in ceylan cinnamon. gamma-Terpineol is isolated from carrot oils, from the cinnamon tree (Cinnamomum zeylanicum) and Scotch pine (Pinus sylvestris).Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. (Wikipedia). Isolated from carrot oils, from the cinnamon tree (Cinnamomum zeylanicum) and Scotch pine (Pinus sylvestris)

   

(+)-Limonene

(4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene

C10H16 (136.1251936)


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

   

(S)-Carvone

D-Carvone 2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-one

C10H14O (150.1044594)


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

   

(S)-alpha-Phellandrene

(5S)-2-Methyl-5-(propan-2-yl)cyclohexa-1,3-diene

C10H16 (136.1251936)


(S)-alpha-Phellandrene is found in ceylan cinnamon. (S)-alpha-Phellandrene is a flavouring agent. (S)-alpha-Phellandrene is a constituent of many essential oils including bitter fennel, elemi and ginger-grass oils. Oil of Ridolfia segetum is a major source (85\\%).Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (Wikipedia Flavouring agent. Constituent of many essential oils including bitter fennel, elemi and ginger-grass oils. Oil of Ridolfia segetum is a major source (85\\%)

   

Isomenthone

(2S-cis)-5-Methyl-2-(1-methylethyl)cyclohexanone

C10H18O (154.1357578)


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

   

(+)-cis-Carveol

(1S,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol

C10H16O (152.12010859999998)


Constituent of dill seed oil (Anethum graveolens). (+)-cis-Carveol is found in dill, caraway, and herbs and spices. (+)-cis-Carveol is found in caraway. (+)-cis-Carveol is a constituent of dill seed oil (Anethum graveolens)

   

(+)-Neomenthol

(1S,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexan-1-ol

C10H20O (156.151407)


Constituent of Japanese peppermint oil. Flavouring ingredient. (+)-Neomenthol is found in many foods, some of which are yellow bell pepper, broccoli, spearmint, and sweet orange. (+)-Neomenthol is found in cabbage. (+)-Neomenthol is a constituent of Japanese peppermint oil. (+)-Neomenthol is a flavouring ingredient (+)-Neomenthol is a potent miticide. (+)-Neomenthol shows acaricidal activitie with LD50 values of 0.32, 0.256 μg/mL for Dermatophagoides farinae and Dermatophagoides pteronyssinus, respectively[1]. (+)-Neomenthol is a potent miticide. (+)-Neomenthol shows acaricidal activitie with LD50 values of 0.32, 0.256 μg/mL for Dermatophagoides farinae and Dermatophagoides pteronyssinus, respectively[1]. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1]. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1]. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1].

   

(+)-Menthone

(2R,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-one

C10H18O (154.1357578)


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

   

Dihydrocarvone

2-Methyl-5-(1-methylethenyl)cyclohexanone, 9ci

C10H16O (152.12010859999998)


Dihydrocarvone, also known as menth-8-en-2-one, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes in plants is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Dihydrocarvone is an essentially neutral compound. It has a warm herbal, minty taste with a spicy minty woody camphoreous flavour ( Ref:DOI ). Dihydrocarvone is found in highest concentrations in spearmints, caraway, and wild celeries and was detected celery stalks, dills, pepper (spice), and peppermints. This could make dihydrocarvone a potential biomarker for the consumption of these foods. Dihydrocarvone is also found in cannabis plants (PMID:6991645 ). Flavouring agent with spearmint-like flavour. Dihydrocarvone is found in many foods, some of which are dill, peppermint, pepper (spice), and caraway.

   

(1S,4S)-Dihydrocarvone

(2S,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one

C10H16O (152.12010859999998)


Constituent of caraway, dill and mint oils. (1S,4S)-Dihydrocarvone is found in many foods, some of which are herbs and spices, caraway, dill, and mentha (mint). (1S,4S)-Dihydrocarvone is found in caraway. (1S,4S)-Dihydrocarvone is a constituent of caraway, dill and mint oils

   

(-)-cis-Carveol

2-Methyl-5-(1-methylethenyl)-(1R-cis)-2-cyclohexen-1-ol

C10H16O (152.12010859999998)


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

   

(-)-beta-Phellandrene

(6R)-3-methylidene-6-(propan-2-yl)cyclohex-1-ene

C10H16 (136.1251936)


(-)-beta-Phellandrene is found in pine nut. Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (Wikipedia).

   

(+)-trans-Carveol

(1R,5S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol

C10H16O (152.12010859999998)


(+)-trans-carveol, also known as (1r,5s)-carveol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (+)-trans-carveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). (+)-trans-carveol can be found in caraway and dill, which makes (+)-trans-carveol a potential biomarker for the consumption of these food products. (+)-trans-Carveol is a metabolite that is a part of arachidonic acid metabolism, linoleic acid metabolism, retinol metabolism, and serotonergic synapse pathways. It is a substrate for cytochrome P450 2C9 and cytochrome P450 2C19.

   

1,2-Cyclohexanediol, 1-methyl-4-(1-methylethenyl)-

1,2-Cyclohexanediol, 1-methyl-4-(1-methylethenyl)-

C10H18O2 (170.1306728)


P-mentha-8(9)-en-1,2-diol, also known as 1-methyl-4-(1-methylethenyl)-1,2-cyclohexanediol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. P-mentha-8(9)-en-1,2-diol is soluble (in water) and a very weakly acidic compound (based on its pKa). P-mentha-8(9)-en-1,2-diol can be found in wild celery, which makes P-mentha-8(9)-en-1,2-diol a potential biomarker for the consumption of this food product.

   

1-Dihydrocarveol

2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol

C10H18O (154.1357578)


Dihydrocarveol, also known as 2-methyl-5-(1-methylethenyl)cyclohexanol or 6-methyl-3-isopropenylcyclohexanol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Dihydrocarveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Dihydrocarveol is a herbal, menthol, and minty tasting compound and can be found in a number of food items such as spearmint, dill, pot marjoram, and pepper (spice), which makes dihydrocarveol a potential biomarker for the consumption of these food products. Dihydrocarveol, also known as 2-methyl-5-(1-methylethenyl)cyclohexanol or 6-methyl-3-isopropenylcyclohexanol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Dihydrocarveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Dihydrocarveol is a herbal, menthol, and minty tasting compound and can be found in a number of food items such as dill, pot marjoram, pepper (spice), and caraway, which makes dihydrocarveol a potential biomarker for the consumption of these food products.

   

Neodihydrocarveol

(1S,2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol

C10H18O (154.1357578)


Neodihydrocarveol, also known as (1r,2s,4r)-neo-dihydrocarveol or (1s,2r,5r)-5-isopropenyl-2-methylcyclohexanol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, neodihydrocarveol is considered to be an isoprenoid lipid molecule. Neodihydrocarveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Neodihydrocarveol can be found in caraway and spearmint, which makes neodihydrocarveol a potential biomarker for the consumption of these food products.

   

Neoisodihydrocarveol

(1R,2S,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol

C10H18O (154.1357578)


Neoisodihydrocarveol, also known as (1s,2r,4r)-neoiso-dihydrocarveol or (1r,2s,5r)-5-isopropenyl-2-methylcyclohexanol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, neoisodihydrocarveol is considered to be an isoprenoid lipid molecule. Neoisodihydrocarveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Neoisodihydrocarveol can be found in caraway and wild celery, which makes neoisodihydrocarveol a potential biomarker for the consumption of these food products.

   

(+)-Neomenthyl acetate

Cyclohexanol,5-methyl-2-(1-methylethyl)-, 1-acetate, (1S,2S,5R)-

C12H22O2 (198.1619712)


(+)-neomenthyl acetate is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (+)-neomenthyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-neomenthyl acetate can be found in orange mint and peppermint, which makes (+)-neomenthyl acetate a potential biomarker for the consumption of these food products.

   

cis-Dihydrocarvone

(2R,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one

C10H16O (152.12010859999998)


Cis-dihydrocarvone, also known as (2r,5s)-2-methyl-5-isopropenylcyclohexanone or (1r,4s)-menth-8-en-2-one, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, cis-dihydrocarvone is considered to be an isoprenoid lipid molecule. Cis-dihydrocarvone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cis-dihydrocarvone is a herbal and warm tasting compound and can be found in a number of food items such as dill, spearmint, wild celery, and common oregano, which makes cis-dihydrocarvone a potential biomarker for the consumption of these food products.

   

(+)-Dihydrocarveol

(1S,2S,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol

C10H18O (154.1357578)


(+)-dihydrocarveol, also known as (1s,2s,5s)-5-isopropenyl-2-methylcyclohexanol or (1s,2s,4s)-menth-8-en-2-ol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (+)-dihydrocarveol is considered to be an isoprenoid lipid molecule (+)-dihydrocarveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). (+)-dihydrocarveol can be found in caraway, which makes (+)-dihydrocarveol a potential biomarker for the consumption of this food product.

   

Perilla sugar

(E)-N-{[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methylidene}hydroxylamine

C10H15NO (165.115358)


Sweetening agent Perillaldehyde, or perilla aldehyde, is a natural organic compound found most abundantly in the annual herb perilla, but also in a wide variety of other plants and essential oils. It is a monoterpenoid containing an aldehyde functional group Sweetening agent Perillartine is a sweetener, which activates the taste receptor type 1 member 2 (Tas1r2) subunit in a species-dependent manner. Perillartine is a sweetener, which activates the taste receptor type 1 member 2 (Tas1r2) subunit in a species-dependent manner.

   

p-Menthan-3-ol

L-Menthol; (-)-Menthol; Levomenthol; Menthomenthol;2-isopropyl-5-methyl-cyclohexanol;Menthol

C10H20O (156.151407)


P-menthan-3-ol is any secondary alcohol that is one of the eight possible diastereoisomers of 5-methyl-2-(propan-2-yl)cyclohexan-1-ol. It has a role as a volatile oil component. It is a p-menthane monoterpenoid and a secondary alcohol. Menthol is a natural product found in Chaerophyllum macrospermum, Mesosphaerum sidifolium, and other organisms with data available. Menthol is an organic compound made synthetically or obtained from peppermint or mint oils with flavoring and local anesthetic properties. When added to pharmaceuticals and foods, menthol functions as a fortifier for peppermint flavors. It also has a counterirritant effect on skin and mucous membranes, thereby producing a local analgesic or anesthetic effect. Menthol is a metabolite found in or produced by Saccharomyces cerevisiae. A monoterpene cyclohexanol produced from mint oils. p-Menthan-3-ol is found in herbs and spices. p-Menthan-3-ol is found in many essential oils.Menthol is an organic compound made synthetically or obtained from peppermint or other mint oils. Natural menthol exists as one pure stereoisomer, nearly always the (1R,2S,5R) form ((-)-menthol). There are 8 possible stereoisomers. (Wikipedia Any secondary alcohol that is one of the eight possible diastereoisomers of 5-methyl-2-(propan-2-yl)cyclohexan-1-ol. C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent D003879 - Dermatologic Agents > D000982 - Antipruritics Found in many essential oils DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1]. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1]. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1]. Menthol is a natural analgesic compound. Menthol could cause a feeling of coolness due to stimulation of ‘cold’ receptors by inhibiting Ca++ currents of neuronal membranes[1]. Menthol is a natural analgesic compound. Menthol could cause a feeling of coolness due to stimulation of ‘cold’ receptors by inhibiting Ca++ currents of neuronal membranes[1].

   

trans-p-Menthane-1,8-diol

CYCLOHEXANEMETHANOL, 4-HYDROXY-.ALPHA.,.ALPHA.,4-TRIMETHYL-, TRANS-

C10H20O2 (172.14632200000003)


Cis-p-menthane-1,8-diol, also known as terpin, titanium (+4) salt or terpin hydrate, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Cis-p-menthane-1,8-diol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Cis-p-menthane-1,8-diol is a bitter tasting compound found in herbs and spices, which makes cis-p-menthane-1,8-diol a potential biomarker for the consumption of this food product. Cis-p-menthane-1,8-diol exists in all eukaryotes, ranging from yeast to humans. Terpin is a p-menthane monoterpenoid. Terpin is a natural product found in Vitis vinifera with data available. Terpin is a metabolite found in or produced by Saccharomyces cerevisiae. cis-p-Menthane-1,8-diol is found in herbs and spices. cis-p-Menthane-1,8-diol is isolated from fruits of California peppertree (Schinus molle D019141 - Respiratory System Agents > D005100 - Expectorants

   

(1S,4R)-p-Mentha-2,8-dien-1-ol

2-Cyclohexen-1-ol, 1-methyl-4-(1-methylethenyl)-, (1S-cis)-

C10H16O (152.12010859999998)


Isolated from gingergrass (Cymbopogon) and Citrus oils. (1S,4R)-p-Mentha-2,8-dien-1-ol is found in many foods, some of which are sweet bay, spearmint, wild celery, and citrus. (1S,4R)-p-Mentha-2,8-dien-1-ol is found in caraway. (1S,4R)-p-Mentha-2,8-dien-1-ol is isolated from gingergrass (Cymbopogon) and Citrus oil (1S,4R)-p-Mentha-2,8-dien-1-ol is a p-menthane monoterpenoid. cis-Isolimonenol ((1S,4R)-p-Mentha-2,8-dien-1-ol) is a chemical composition of essential oil[1].

   

Pulegone

Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (theta)-

C10H16O (152.12010859999998)


Pulegone belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. It is formally classified as a cyclic ketone although it is biochemically a monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Pulegone is a hydrophobic, neutral compound that is insoluble in water. It exists as a clear, colorless oil. There are two isomers of Pulegone (the R and the S isomer), with the R isomer being more common. It is used industrially as a food additive and a perfuming agent. Pulegone has a fresh, minty or peppermint odor and a minty, fruity or green taste. It is found naturally in the essential oils of a variety of plants such as Nepeta cataria (catnip), Hedeoma pulegioides (pennyroyal), and Mentha species. It is also found in a number of plant foods and spices such as blackberryies, black currants, bell peppers, cornmint, rosemary, black tea, thyme, orange mint, peppermint, and spearmint, which makes it a potential biomarker for the consumption of these food products. Pulegone is also one of more than 140 terpenes that are found in cannabis plants (PMID:6991645 ). Pulegone, also known as (+)-(R)-pulegone or (1r)-(+)-P-menth-4(8)-en-3-one, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, pulegone is considered to be an isoprenoid lipid molecule. Pulegone is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Pulegone can be found in a number of food items such as globe artichoke, sacred lotus, garden onion, and rubus (blackberry, raspberry), which makes pulegone a potential biomarker for the consumption of these food products. Pulegone can be found primarily in saliva. Pulegone is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as Nepeta cataria (catnip), Mentha piperita, and pennyroyal. It is classified as a monoterpene . (+)-pulegone is the (5R)-enantiomer of p-menth-4(8)-en-3-one. Pulegone is a natural product found in Hedeoma multiflora, Clinopodium dalmaticum, and other organisms with data available. See also: Agathosma betulina leaf (part of). The (5R)-enantiomer of p-menth-4(8)-en-3-one. Pulegone, the major chemical constituent of Nepeta catariaessential oil which is an aromatic herb, is one of avian repellents[1]. The molecular target for the repellent action of Pulegone in avian species is nociceptive TRP ankyrin 1 (TRPA1). Pulegone stimulates both TRPM8 and TRPA1 channel in chicken sensory neurons and suppresses the former but not the latter at high concentrations[2]. Pulegone, the major chemical constituent of Nepeta catariaessential oil which is an aromatic herb, is one of avian repellents[1]. The molecular target for the repellent action of Pulegone in avian species is nociceptive TRP ankyrin 1 (TRPA1). Pulegone stimulates both TRPM8 and TRPA1 channel in chicken sensory neurons and suppresses the former but not the latter at high concentrations[2].

   

Piperitone

2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (S)-

C10H16O (152.12010859999998)


Piperitone is found in ceylan cinnamon. Piperitone is a flavouring ingredient.Piperitone is a natural monoterpene ketone which is a component of some essential oils. Both stereoisomers, the D-form and the L-form, are known. The D-form has a peppermint-like aroma and has been isolated from the oils of plants from the genera Cymbopogon, Andropogon, and Mentha. The L-form has been isolated from Sitka spruce. (Wikipedia Piperitone is a p-menthane monoterpenoid that is cyclohex-2-en-1-one substituted by a methyl group at position 3 and an isopropyl group at position 6. It has a role as a volatile oil component and a plant metabolite. It is a p-menthane monoterpenoid and a cyclic terpene ketone. Piperitone is a natural product found in Clinopodium dalmaticum, Eucalyptus fasciculosa, and other organisms with data available. A p-menthane monoterpenoid that is cyclohex-2-en-1-one substituted by a methyl group at position 3 and an isopropyl group at position 6. Flavouring ingredient Piperitone is as a powerful repellent and antiappetent agent. Piperitone is very toxic to Cymbopogon schoenanthus (C. schoenanthus) adults, newly laid eggs and to neonate larvae. Insecticidal activity[1]. Piperitone is as a powerful repellent and antiappetent agent. Piperitone is very toxic to Cymbopogon schoenanthus (C. schoenanthus) adults, newly laid eggs and to neonate larvae. Insecticidal activity[1].

   

Carveol

(1S-trans)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-ol

C10H16O (152.12010859999998)


Carveol is a clear colorless liquid. Insoluble in water. Carveol is a limonene monoterpenoid that is cyclohex-2-en-1-ol substituted by a methyl group at position 2 and a prop-1-en-2-yl group at position 5. It has a role as a volatile oil component and a plant metabolite. Carveol is a natural product found in Echinophora tournefortii, Trachyspermum anethifolium, and other organisms with data available. Present in oil of grapefruit (Citrus paradisi), mandarin (Citrus reticulata), blackcurrant berries, celery, black tea, dill, caraway seeds and lambs lettuce. Flavouring agent. Carveol is found in many foods, some of which are fruits, parsley, tea, and cumin. Carveol is found in caraway. Carveol is present in oil of grapefruit (Citrus paradisi), mandarin (Citrus reticulata), blackcurrant berries, celery, black tea, dill, caraway seeds and lambs lettuce. Carveol is a flavouring agent A limonene monoterpenoid that is cyclohex-2-en-1-ol substituted by a methyl group at position 2 and a prop-1-en-2-yl group at position 5. Carveol is an endogenous metabolite. Carveol is an endogenous metabolite.

   

Kahweol

17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-ol

C20H26O3 (314.1881846)


Pulegone, also known as (+)-(R)-pulegone or (1r)-(+)-P-menth-4(8)-en-3-one, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, pulegone is considered to be an isoprenoid lipid molecule. Pulegone is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Pulegone can be found in a number of food items such as globe artichoke, sacred lotus, garden onion, and rubus (blackberry, raspberry), which makes pulegone a potential biomarker for the consumption of these food products. Pulegone can be found primarily in saliva. Pulegone is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as Nepeta cataria (catnip), Mentha piperita, and pennyroyal. It is classified as a monoterpene . Kahweol is found in arabica coffee. Kahweol is present in boiled type-coffee beverages. May possess hypercholesterolaemic activity. Constit of coffee bean oil Kahweol is a diterpene molecule found in the beans of Coffea arabica. It is structurally related to cafestol Kahweol is one of the consituents of the coffee from Coffea Arabica with anti-inflammatory anti-angiogenic, and anti-cancerous activities. Kahweol inhibits adipogenesis and increase glucose uptake by AMP-activated protein kinase (AMPK) activation. Kahweol induces apoptosis. Kahweol is one of the consituents of the coffee from Coffea Arabica with anti-inflammatory anti-angiogenic, and anti-cancerous activities. Kahweol inhibits adipogenesis and increase glucose uptake by AMP-activated protein kinase (AMPK) activation. Kahweol induces apoptosis.

   

Acoric acid

(3S)-3-[(1S,4R)-4-methyl-1-(2-methylpropanoyl)-3-oxocyclohexyl]butanoic acid

C15H24O4 (268.1674504)


Acoric acid is found in herbs and spices. Acoric acid is a constituent of Acorus calamus (sweet flag) Felypressin is a synthetic analog of lypressin or vasopressin with more vasoconstrictor activity than antidiuretic action. It is used primarily as a hemostatic. Felypressin is a non-catecholamine vasoconstrictor that is chemically related to vasopressin, the posterior pituitary hormone. Constituent of Acorus calamus (sweet flag) [DFC]. Acoric acid is found in herbs and spices and root vegetables. D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents > D014667 - Vasopressins D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

   

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

(1S)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol

C10H18O (154.1357578)


(S)-p-Menth-1-en-4-ol occurs in many essential oils, e.g. lavende Occurs in many essential oils, e.g. lavender Terpinen-4-ol (4-Carvomenthenol), a naturally occurring monoterpene, is the main bioactive component of tea-tree oil. Terpinen-4-ol suppresses inflammatory mediator production by activated human monocytes. Terpinen-4-ol significantly enhances the effect of several chemotherapeutic and biological agents[1][2][3]. Terpinen-4-ol (4-Carvomenthenol), a naturally occurring monoterpene, is the main bioactive component of tea-tree oil. Terpinen-4-ol suppresses inflammatory mediator production by activated human monocytes. Terpinen-4-ol significantly enhances the effect of several chemotherapeutic and biological agents[1][2][3].

   

p-Menthan-4-ol

4-methyl-1-(propan-2-yl)cyclohexan-1-ol

C10H20O (156.151407)


p-Menthan-4-ol is found in mentha (mint). p-Menthan-4-ol is present in turpentine from Pinus sylvestris (Scotch pine Present in turpentine from Pinus sylvestris (Scotch pine). p-Menthan-4-ol is found in mentha (mint).

   

Carvyl acetate

2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, 1-acetate

C12H18O2 (194.1306728)


Flavouring ingredient. Carvyl acetate is found in wild celery, caraway, and peppermint. Carvyl acetate is found in caraway. Carvyl acetate is a flavouring ingredient.

   

5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone

3-methyl-4-[2-methyl-3,4-dioxo-5-(propan-2-yl)cyclohexa-1,5-dien-1-yl]-6-(propan-2-yl)cyclohexa-3,5-diene-1,2-dione

C20H22O4 (326.1518012)


5,5-Diisopropyl-2,2-dimethylbiphenyl-3,3,4,4-tetrone is found in herbs and spices. 5,5-Diisopropyl-2,2-dimethylbiphenyl-3,3,4,4-tetrone is a constituent of the leaves of thyme Thymus vulgaris. Shows antioxidant activity. Constituent of the leaves of thyme Thymus vulgaris. Shows antioxidant activity. 5,5-Diisopropyl-2,2-dimethylbiphenyl-3,3,4,4-tetrone is found in herbs and spices.

   

cis-p-Menthane-1,7,8-triol

1-(hydroxymethyl)-4-(2-hydroxypropan-2-yl)cyclohexan-1-ol

C10H20O3 (188.14123700000002)


trans-p-Menthane-1,7,8-triol is found in herbs and spices. trans-p-Menthane-1,7,8-triol is a constituent of Foeniculum vulgare (fennel) Constituent of Foeniculum vulgare (fennel). cis-p-Menthane-1,7,8-triol is found in herbs and spices.

   

xi-p-Mentha-3,8-dien-1-ol

1-methyl-4-(prop-1-en-2-yl)cyclohex-3-en-1-ol

C10H16O (152.12010859999998)


xi-p-Mentha-3,8-dien-1-ol is found in herbs and spices. xi-p-Mentha-3,8-dien-1-ol is isolated from black pepper oil. Isolated from black pepper oil. xi-p-Mentha-3,8-dien-1-ol is found in herbs and spices.

   

p-Menth-8-en-3-ol

5-Methyl-2-(1-methylethenyl)cyclohexanol, 9ci

C10H18O (154.1357578)


Various stereoisomers occur in essential oils. p-Menth-8-en-3-ol is a flavouring agent Various stereoisomers occur in essential oils. Flavouring agent

   

(2S,4R)-p-Mentha-1(7),5-dien-2-ol

2-methylidene-5-(propan-2-yl)cyclohex-3-en-1-ol

C10H16O (152.12010859999998)


(2S,4R)-p-Mentha-1(7),5-dien-2-ol is found in herbs and spices. (2S,4R)-p-Mentha-1(7),5-dien-2-ol is a constituent of Piper nigrum (pepper). Constituent of Piper nigrum (pepper). (2S,4R)-p-Mentha-1(7),5-dien-2-ol is found in herbs and spices and pepper (spice).

   

(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one

5-(1,2-dihydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one

C10H16O3 (184.1099386)


(4S,8S)-8,9-Dihydroxy-p-menth-1(6)-en-2-one is found in herbs and spices. (4S,8S)-8,9-Dihydroxy-p-menth-1(6)-en-2-one is a constituent of fruit of Carum carvi (caraway). Constituent of fruit of Carum carvi (caraway). (4S,8S)-8,9-Dihydroxy-p-menth-1(6)-en-2-one is found in herbs and spices.

   

cis-Isopulegone

[4-(prop-1-en-2-yl)cyclohexyl]methanol

C10H18O (154.1357578)


cis-Isopulegone is found in fats and oils. cis-Isopulegone is a minor constituent of Perilla species. Minor constituent of Perilla subspecies cis-Isopulegone is found in fats and oils.

   

(1R,2R,4R,8R)-p-Menthane-2,8,9-triol

2-(3-hydroxy-4-methylcyclohexyl)propane-1,2-diol

C10H20O3 (188.14123700000002)


(1S*,2S*,4R*,8S*)-p-Menthane-2,8,9-triol is found in fats and oils. (1S*,2S*,4R*,8S*)-p-Menthane-2,8,9-triol is a constituent of fruit of Carum carvi (caraway).

   

(1R,2R,4S)-p-Menthane-1,2,8-triol

4-(2-hydroxypropan-2-yl)-1-methylcyclohexane-1,2-diol

C10H20O3 (188.14123700000002)


(1R,2R,4S)-p-Menthane-1,2,8-triol is found in fats and oils. (1R,2R,4S)-p-Menthane-1,2,8-triol is a constituent of fruit of Carum carvi (caraway). Constituent of fruit of Carum carvi (caraway). (1R,2R,4S)-p-Menthane-1,2,8-triol is found in fats and oils and herbs and spices.

   

(S)-Phellandral

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

C10H16O (152.12010859999998)


(S)-Phellandral is found in herbs and spices. (S)-Phellandral is a constituent of Anethum sowa (Indian dill) Constituent of Anethum sowa (Indian dill). (S)-Phellandral is found in herbs and spices.

   

(S)-Menthone 8-thioacetate

(2S,5S)-2-[2-(Acetylsulphanyl)propan-2-yl]-5-methylcyclohexan-1-one

C12H20O2S (228.11839400000002)


(S)-Menthone 8-thioacetate is present in Buchu leaf oil. (S)-Menthone 8-thioacetate is a flavouring ingredient. Present in Buchu leaf oil. Flavouring ingredient

   

(R)-p-Mentha-1,8-dien-10-ol

1-Methyl-4-((hydroxymethyl)vinyl)-cyclohex-1-ene

C10H16O (152.12010859999998)


(R)-p-Mentha-1,8-dien-10-ol is a citrus-like flavouring agent [CCD]. Citrus-like flavouring agent [CCD]

   

p-Menthan-1-ol

Cyclohexane, 1-methyl-4-(1-methylethyl)-, hydroxy deriv.

C10H20O (156.151407)


p-Menthan-1-ol is found in herbs and spices. p-Menthan-1-ol is isolated from spearmint oil. Isolated from spearmint oil. p-Menthan-1-ol is found in herbs and spices.

   

Isovitexin 2'-(6'-feruloylglucoside) 4'-glucoside

[6-({2-[5,7-dihydroxy-4-oxo-2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4H-chromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

C43H48O23 (932.2586258)


Isovitexin 2-(6-feruloylglucoside) 4-glucoside is found in fruits. Isovitexin 2-(6-feruloylglucoside) 4-glucoside is a constituent of Cucumis sativus (cucumber). Constituent of Cucumis sativus (cucumber). Isovitexin 2-(6-feruloylglucoside) 4-glucoside is found in cucumber and fruits.

   

p-Menth-1-en-9-ol

beta,4-Dimethyl-(R-(r*,r*))-3-cyclohexene-1-ethanol

C10H18O (154.1357578)


Constituent of Vaccinium myrtillus (bilberry) and tangerine oil. p-Menth-1-en-9-ol is found in many foods, some of which are bilberry, citrus, lemon, and fruits. p-Menth-1-en-9-ol is found in bilberry. p-Menth-1-en-9-ol is a constituent of Vaccinium myrtillus (bilberry) and tangerine oil.

   

Dihydrocarveol acetate

2-Methyl-5-(prop-1-en-2-yl)cyclohexyl acetic acid

C12H20O2 (196.14632200000003)


Flavouring ingredient. Dihydrocarveol acetate is found in many foods, some of which are caraway, wild celery, spearmint, and anise. Dihydrocarveol acetate is found in anise. Dihydrocarveol acetate is a flavouring ingredient.

   

(2S,4R)-p-Mentha-1(7),8-dien-2-ol

2-methylidene-5-(prop-1-en-2-yl)cyclohexan-1-ol

C10H16O (152.12010859999998)


(2s,4r)-p-mentha-1(7),8-dien-2-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (2s,4r)-p-mentha-1(7),8-dien-2-ol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). (2s,4r)-p-mentha-1(7),8-dien-2-ol can be found in herbs and spices, which makes (2s,4r)-p-mentha-1(7),8-dien-2-ol a potential biomarker for the consumption of this food product. (2S,4R)-p-Mentha-1(7),8-dien-2-ol is found in herbs and spices. (2S,4R)-p-Mentha-1(7),8-dien-2-ol is isolated from Zanthoxylum piperitum (Japanese pepper tree).

   

(-)-Carvomenthone

(2S,5S)-2-methyl-5-(propan-2-yl)cyclohexan-1-one

C10H18O (154.1357578)


Isolated from oils of Tanacetum vulgare (tansy). (-)-Carvomenthone is found in cornmint and herbs and spices. (-)-Carvomenthone is found in cornmint. (-)-Carvomenthone is isolated from oils of Tanacetum vulgare (tansy

   

Calacone

6-methyl-2-(3-methylbut-3-en-1-yl)-3-(propan-2-yl)cyclohex-2-en-1-one

C15H24O (220.18270539999997)


Constituent of Acorus calamus (sweet flag). Calacone is found in herbs and spices and root vegetables. Calacone is found in herbs and spices. Calacone is a constituent of Acorus calamus (sweet flag).

   

(1R,2S,3S,4R)-p-Menthane-2,3-diol

3-methyl-6-(propan-2-yl)cyclohexane-1,2-diol

C10H20O2 (172.14632200000003)


(1R,2S,3S,4R)-p-Menthane-2,3-diol is found in herbs and spices. (1R,2S,3S,4R)-p-Menthane-2,3-diol is isolated from peppermint oi Isolated from peppermint oil. (1R,2S,3S,4R)-p-Menthane-2,3-diol is found in herbs and spices.

   

(1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol

4-(1,2-dihydroxypropan-2-yl)-1-methylcyclohexane-1,2-diol

C10H20O4 (204.136152)


(1S*,2R*,4R*,8S*)-p-Menthane-1,2,8,9-tetrol is found in fats and oils. (1S*,2R*,4R*,8S*)-p-Menthane-1,2,8,9-tetrol is a constituent of fruit of Carum carvi (caraway).

   

3-Hydroxy-p-mentha-1,8-dien-7-al

3-hydroxy-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde

C10H14O2 (166.09937440000002)


3-Hydroxy-p-mentha-1,8-dien-7-al is found in fats and oils. 3-Hydroxy-p-mentha-1,8-dien-7-al is a constituent of Perilla frutescens (perilla). Constituent of Perilla frutescens (perilla). 3-Hydroxy-p-mentha-1,8-dien-7-al is found in fats and oils and herbs and spices.

   

trans-p-Menth-2-ene-1,4-diol

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

C10H18O2 (170.1306728)


trans-p-Menth-2-ene-1,4-diol is found in herbs and spices. trans-p-Menth-2-ene-1,4-diol is isolated from peppermint oil and Chenopodium ambroisioides. Isolated from peppermint oil and Chenopodium ambroisioides. trans-p-Menth-2-ene-1,4-diol is found in herbs and spices.

   

(R)-Carvotanacetone

2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-one

C10H16O (152.12010859999998)


(R)-Carvotanacetone is found in fruits. (R)-Carvotanacetone is a constituent of Piper nigrum (pepper) and Cymbopogon nardus (citronella). Also from Tanacetum vulgare (tansy) D000970 - Antineoplastic Agents

   

Isoterpinolene

3-methyl-6-(propan-2-ylidene)cyclohex-1-ene

C10H16 (136.1251936)


P-mentha-2,4(8)-diene is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. P-mentha-2,4(8)-diene can be found in dill, which makes P-mentha-2,4(8)-diene a potential biomarker for the consumption of this food product. P-mentha-2,4(8)-diene can be found primarily in saliva. Isoterpinolene belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

   

(S)-Oleuropeic acid

4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid

C10H16O3 (184.1099386)


Oleuropeic acid, also known as rac-oleuropeate, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Oleuropeic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Oleuropeic acid can be found in olive, which makes oleuropeic acid a potential biomarker for the consumption of this food product. (S)-Oleuropeic acid is found in fats and oils. Aglycone from Olea europaea (olive).

   

Withangulatin A

15-[1-(4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetic acid

C30H38O8 (526.2566548)


Withangulatin A is found in fruits. Withangulatin A is a constituent of the famine food Physalis angulata (cutleaf ground cherry).

   

Avenacoside A

2-{[4-hydroxy-2-(hydroxymethyl)-6-[5,7,9,13-tetramethyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5-oxaspiro[oxolane-2,6-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18-eneoxy]-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

C51H82O23 (1062.5246622)


Avenacoside A is found in cereals and cereal products. Avenacoside A is a constituent of Avena sativa (oats).

   

p-Mentha-1(6),8-dien-3-ol

3-Methyl-6-(1-methylethenyl)-3-cyclohexen-1-ol, 9ci

C10H16O (152.12010859999998)


p-Mentha-1(6),8-dien-3-ol is found in fats and oils. p-Mentha-1(6),8-dien-3-ol is isolated from lemongrass oi Isolated from lemongrass oil. p-Mentha-1(6),8-dien-3-ol is found in fats and oils.

   

xi-p-Menth-3-ene

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

C10H18 (138.1408428)


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.

   

(±)-Carvomenthol

(1ALPHA,2BETA,5ALPHA)-5-(ISOPROPYL)-2-METHYLCYCLOHEXAN-1-OL

C10H20O (156.151407)


(±)-Carvomenthol is a flavouring ingredient. Flavouring ingredient

   

delta-Terpineol

alpha,alpha-Dimethyl-4-Methylenecyclohexanemethanol

C10H18O (154.1357578)


Isolated from Zanthoxylum piperitum (Japanese pepper tree). delta-Terpineol is found in many foods, some of which are spearmint, cardamom, herbs and spices, and rosemary. delta-Terpineol is found in cardamom. delta-Terpineol is isolated from Zanthoxylum piperitum (Japanese pepper tree).

   

5-Hydroxy-p-mentha-6,8-dien-2-one

4-Hydroxy-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one, 9ci

C10H14O2 (166.09937440000002)


5-Hydroxy-p-mentha-6,8-dien-2-one is found in herbs and spices. 5-Hydroxy-p-mentha-6,8-dien-2-one is isolated from spearmint oil. Isolated from spearmint oil. 5-Hydroxy-p-mentha-6,8-dien-2-one is found in herbs and spices.

   

(R)-8-Acetoxycarvotanacetone

2-(4-Methyl-5-oxocyclohex-3-en-1-yl)propan-2-yl acetic acid

C12H18O3 (210.1255878)


(R)-8-Acetoxycarvotanacetone is found in herbs and spices. (R)-8-Acetoxycarvotanacetone is a constituent of cardamom oil. Constituent of cardamom oil. (R)-8-Acetoxycarvotanacetone is found in herbs and spices.

   

p-Menth-1-ene-8-thiol

alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanethiol

C10H18S (170.1129148)


p-Menth-1-ene-8-thiol is found in citrus. p-Menth-1-ene-8-thiol is a powerful flavour constituent of grapefruit juice detectable at 10 4 ppb (equiv. to 10 4 mg per ton of water Powerful flavour constituent of grapefruit juice detectable at 10?4 ppb (equiv. to 10?4 mg per ton of water). p-Menth-1-ene-8-thiol is found in citrus.

   

gamma-Diosphenol

2-Hydroxy-6-methyl-3-(1-methylethyl)-2-cyclohexen-1-one, 9ci

C10H16O2 (168.1150236)


gamma-Diosphenol is a constituent of Agathosma betulina leaf oil (buchu). Constituent of Agathosma betulina leaf oil (buchu)

   

10alpha-4,5-Seco-11-eudesmene-4,5-dione

2-methyl-2-(4-oxopentyl)-5-(prop-1-en-2-yl)cyclohexan-1-one

C15H24O2 (236.1776204)


Constituent of Cyperus rotundus (nutgrass). 10alpha-4,5-Seco-11-eudesmene-4,5-dione is found in root vegetables. Azoridione is found in root vegetables. Azoridione is a constituent of Cyperus rotundus (nutgrass)

   

(1beta,2beta,5beta)-p-Menth-3-ene-1,2,5-triol

2-methyl-5-(propan-2-yl)cyclohex-5-ene-1,2,4-triol

C10H18O3 (186.1255878)


(1beta,2beta,5beta)-p-Menth-3-ene-1,2,5-triol is a constituent of Carum ajowan (ajowan). Constituent of Carum ajowan (ajowan)

   

p-Mentha-1,3,8-triene

1-Methyl-4-(1-methylethenyl)-1,3-cyclohexadiene, 9ci

C10H14 (134.1095444)


Isolated from Petroselinum sativum (Yugoslavian parsley). p-Mentha-1,3,8-triene is found in dill, herbs and spices, and parsley. p-Mentha-1,3,8-triene is found in dill. p-Mentha-1,3,8-triene is isolated from Petroselinum sativum (Yugoslavian parsley).

   

(1S,3R,4R)-p-Menthane-1,3-diol

1-methyl-4-(propan-2-yl)cyclohexane-1,3-diol

C10H20O2 (172.14632200000003)


(1S,3R,4R)-p-Menthane-1,3-diol is found in herbs and spices. (1S,3R,4R)-p-Menthane-1,3-diol is isolated from peppermint oil. Isolated from peppermint oil. (1S,3R,4R)-p-Menthane-1,3-diol is found in herbs and spices.

   

p-Mentha-1,8-dien-4-ol

4-Methyl-1-(1-methylethenyl)-3-cyclohexen-1-ol, 9ci

C10H16O (152.12010859999998)


Isolated from Japanese pepper tree (Zanthoxylum piperitum), yuzu (Citrus junos), and spearmint (Mentha spicata) oils. p-Mentha-1,8-dien-4-ol is found in many foods, some of which are spearmint, pepper (spice), caraway, and blackcurrant. p-Mentha-1,8-dien-4-ol is found in blackcurrant. p-Mentha-1,8-dien-4-ol is isolated from Japanese pepper tree (Zanthoxylum piperitum), yuzu (Citrus junos), and spearmint (Mentha spicata) oils.

   

Lansic acid

3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid

C30H46O4 (470.3395916)


Lansic acid is found in fruits. Lansic acid is a constituent of Lansium domesticum (langsat). Constituent of Lansium domesticum (langsat). Lansic acid is found in fruits.

   

Momordicin I

5,9-dihydroxy-14-(4-hydroxy-6-methylhept-5-en-2-yl)-6,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

C30H48O4 (472.3552408)


Momordicin I is found in bitter gourd. Momordicin I is a constituent of leaves and vines of Momordica charantia (bitter melon)

   

(1S,2S,4R,8R)-p-Menthane-1,2,9-triol

4-(1-hydroxypropan-2-yl)-1-methylcyclohexane-1,2-diol

C10H20O3 (188.14123700000002)


(1S,2S,4R,8R)-p-Menthane-1,2,9-triol is found in herbs and spices. (1S,2S,4R,8R)-p-Menthane-1,2,9-triol is a constituent of caraway fruits. Constituent of caraway fruits. (1S,2S,4R,8R)-p-Menthane-1,2,9-triol is found in herbs and spices.

   

xi-p-Menth-3-en-1-ol

1-methyl-4-(propan-2-yl)cyclohex-3-en-1-ol

C10H18O (154.1357578)


Constituent of oregano (Origanum vulgare), lime peel (Citrus aurantifolia) and mandarin peeland is) also present in grapefruit juice, cognac, wines, cocoa, black tea and cardamon. Flavouring agent. xi-p-Menth-3-en-1-ol is found in many foods, some of which are herbs and spices, cocoa and cocoa products, citrus, and tea. xi-p-Menth-3-en-1-ol is found in alcoholic beverages. xi-p-Menth-3-en-1-ol is a constituent of oregano (Origanum vulgare), lime peel (Citrus aurantifolia) and mandarin peel. Also present in grapefruit juice, cognac, wines, cocoa, black tea and cardamon. xi-p-Menth-3-en-1-ol is a flavouring agent.

   

8-Mercapto-p-menthan-3-one

trans-2-(1-mercapto-1-Methylethyl)-5-methylcyclohexan-1-one

C10H18OS (186.1078298)


8-Mercapto-p-menthan-3-one is a mixture of stereoisomers is used as a blackcurrant flavour. A mixture of stereoisomers is used as a blackcurrant flavour

   

(R)-2-Acetoxy-p-mentha-1,8-diene

2-Methyl-5-(prop-1-en-2-yl)cyclohex-1-en-1-yl acetic acid

C12H18O2 (194.1306728)


(R)-2-Acetoxy-p-mentha-1,8-diene is found in citrus. (R)-2-Acetoxy-p-mentha-1,8-diene is isolated from grapefruit oil. Isolated from grapefruit oil. (R)-2-Acetoxy-p-mentha-1,8-diene is found in citrus.

   

xi-p-Mentha-1(7),2-dien-4-ol

4-methylidene-1-(propan-2-yl)cyclohex-2-en-1-ol

C10H16O (152.12010859999998)


xi-p-Mentha-1(7),2-dien-4-ol is found in herbs and spices. xi-p-Mentha-1(7),2-dien-4-ol is isolated from black pepper oil. Isolated from black pepper oil. xi-p-Mentha-1(7),2-dien-4-ol is found in herbs and spices.

   

Perillyl acetate

1-Cyclohexene-1-methanol, 4-(1-methylethenyl)-, 1-acetate

C12H18O2 (194.1306728)


Perillyl acetate is found in mandarin orange (clementine, tangerine). Perillyl acetate is a flavouring ingredient. Flavouring ingredient. Perillyl acetate is found in sunflower.

   

(1alpha,2alpha,4betaH,6alpha,8R)-p-Menthane-2,6,8,9-tetrol

(1alpha,2alpha,4betaH,6alpha,8R)-p-Menthane-2,6,8,9-tetrol

C10H20O4 (204.136152)


(1alpha,2alpha,4betaH,6alpha,8R)-p-Menthane-2,6,8,9-tetrol is found in herbs and spices. (1alpha,2alpha,4betaH,6alpha,8R)-p-Menthane-2,6,8,9-tetrol is a constituent of fruit of Carum carvi (caraway). Constituent of fruit of Carum carvi (caraway). (1alpha,2alpha,4betaH,6alpha,8R)-p-Menthane-2,6,8,9-tetrol is found in herbs and spices.

   

Menthyl isovalerate

(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 3-methylbutanoic acid

C15H28O2 (240.20891880000002)


Menthyl isovalerate is found in peppermint. Menthyl isovalerate is a flavouring ingredient with a bitter, wood-like taste. Flavouring ingredient with a bitter, wood-like taste. Menthyl isovalerate is found in peppermint.

   

2-Hydroxy-p-mentha-1,8-dien-6-one

3-Hydroxy-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one

C10H14O2 (166.09937440000002)


2-Hydroxy-p-mentha-1,8-dien-6-one is found in herbs and spices. 2-Hydroxy-p-mentha-1,8-dien-6-one is isolated from spearmint oil. Isolated from spearmint oil. 2-Hydroxy-p-mentha-1,8-dien-6-one is found in herbs and spices.

   

(S)-p-Mentha-1,8-dien-10-yl acetate

2-(4-Methylcyclohex-3-en-1-yl)prop-2-en-1-yl acetic acid

C12H18O2 (194.1306728)


(S)-p-Mentha-1,8-dien-10-yl acetate is found in citrus. (S)-p-Mentha-1,8-dien-10-yl acetate is isolated from grapefruit, lemon and mandarin oils. Isolated from Citrus natsudaidai oil. (±)-p-Mentha-1,8-dien-10-yl acetate is found in lemon, citrus, and fats and oils.

   

Simulanoquinoline

2-({17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-20-yl}methyl)-7-methoxy-2,6-dimethyl-2H,5H,6H-pyrano[3,2-c]quinolin-5-one

C37H34N2O7 (618.2365894)


Simulanoquinoline is found in fruits. Simulanoquinoline is an alkaloid from root bark of Zanthoxylum simulans (Szechuan pepper).

   

p-Menthane

1-Methyl-4-(1-methylethyl)-cyclohexane

C10H20 (140.15649200000001)


p-Menthane is found in peppermint. p-Menthane is a flavouring compound [Goodscents A flavouring compound [Goodscents]. p-Menthane is found in peppermint.

   

p-Mentha-2,4-diene

5-Methyl-2-(1-methylethyl)-1,3-cyclohexadiene

C10H16 (136.1251936)


p-Mentha-2,4-diene is found in citrus. p-Mentha-2,4-diene is a constituent of Valencia orange oil. Constituent of Valencia orange oil. p-Mentha-2,4-diene is found in citrus.

   

Saponin D

2-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-16-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-7-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

C48H78O17 (926.5238738)


Saponin D is a constituent of Hovenia dulcis (raisin tree).

   

Isolimonene

(3R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-1-ene

C10H16 (136.1251936)


Isolimonene belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

   

5-Isopropyl-2-(2-methylpropyl)-2-cyclohexen-1-one

5-(1-Methylethyl)-2-(2-methylpropyl)-2-cyclohexen-1-one, 9ci

C13H22O (194.1670562)


5-Isopropyl-2-(2-methylpropyl)-2-cyclohexen-1-one is found in herbs and spices. 5-Isopropyl-2-(2-methylpropyl)-2-cyclohexen-1-one is a constituent of Anthemis nobilis (Roman chamomile). Constituent of Anthemis nobilis (Roman chamomile). 5-Isopropyl-2-(2-methylpropyl)-2-cyclohexen-1-one is found in tea and herbs and spices.

   

p-Menth-1-en-9-al

alpha,4-Dimethyl-3-cyclohexene-1-acetaldehyde

C10H16O (152.12010859999998)


P-menth-1-ene-9-al, also known as alpha,4-dimethyl-3-cyclohexene-1-acetaldehyde, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. P-menth-1-ene-9-al is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). P-menth-1-ene-9-al is a herbal and spicy tasting compound found in wild celery, which makes P-menth-1-ene-9-al a potential biomarker for the consumption of this food product. p-Menth-1-en-9-al belongs to the family of Monocyclic Monoterpenes. These are monoterpenes containing 1 ring in the isoprene chain

   

Terpinolene oxide

2,2,6-Trimethyl-1-oxaspiro(2.5)oct-5-ene

C10H16O (152.12010859999998)


Isolated from Zanthoxylum piperitum (Japanese pepper tree). Terpinolene oxide is found in cumin and herbs and spices. Terpinolene oxide is found in cumin. Terpinolene oxide is isolated from Zanthoxylum piperitum (Japanese pepper tree).

   

Menthanol

trans-(1)-alpha,alpha,4-Trimethylcyclohexanemethanol

C10H20O (156.151407)


Present in lemon and spearmint oils. Menthanol is found in citrus, fats and oils, and pine nut. Menthanol is found in citrus. Menthanol is present in lemon and spearmint oil

   

beta-Terpinene

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

C10H16 (136.1251936)


beta-Terpinene is found in cumin. beta-Terpinene is a constituent of Juniper and Myrica gale (bog myrtle) oils.The terpinenes are three isomeric hydrocarbons that are classified as terpenes. They each have the same molecular formula and carbon framework, but they differ in the position of carbon-carbon double bonds. alpha-Terpinene has been isolated from cardamom and marjoram oils, and from other natural sources. beta-Terpinene has no known natural source, but has been prepared synthetically from sabinene. gamma-Terpinene is natural and has been isolated from a variety of plant sources. (Wikipedia). Constituent of Juniper and Myrica gale (bog myrtle) oils

   

p-Menth-1-en-5-ol

3-Methyl-6-(1-methylethyl)-3-cyclohexen-1-ol

C10H18O (154.1357578)


Isolated from Piper nigrum (pepper). p-Menth-1-en-5-ol is found in herbs and spices, fruits, and pepper (spice). p-Menth-1-en-5-ol is found in fruits. p-Menth-1-en-5-ol is isolated from Piper nigrum (pepper).

   

(R)-2-Nitro-p-mentha-1,5-diene

(5R)-2-methyl-1-nitro-5-(propan-2-yl)cyclohexa-1,3-diene

C10H15NO2 (181.110273)


Constituent of Angelica archangelica (angelica). (R)-2-Nitro-p-mentha-1,5-diene is found in fats and oils, herbs and spices, and green vegetables. (R)-2-Nitro-p-mentha-1,5-diene is found in fats and oils. (R)-2-Nitro-p-mentha-1,5-diene is a constituent of Angelica archangelica (angelica)

   

cis-6-Nitro-p-mentha-1(7),2-diene

(4R-cis)-3-Methylene-6-(1-methylethyl)-4-nitrocyclohexene

C10H15NO2 (181.110273)


Constituent of Angelica archangelica (angelica). cis-6-Nitro-p-mentha-1(7),2-diene is found in fats and oils, herbs and spices, and green vegetables. trans-6-Nitro-p-mentha-1(7),2-dien is found in fats and oils. trans-6-Nitro-p-mentha-1(7),2-dien is a constituent of Angelica archangelica (angelica)

   

Limonene aldehyde

3-(4-Methylcyclohex-3-en-1-yl)butyraldehyde

C11H18O (166.1357578)


Limonene aldehyde is a flavouring ingredien Flavouring ingredient

   

p-Menth-3-en-9-al

a,4-Dimethyl-1-cyclohexene-1-acetaldehyde, 9ci

C10H16O (152.12010859999998)


Constituent of Spanish oregano (Coridothymus capitatus), Origanum subspecies and blackberries. p-Menth-3-en-9-al is found in herbs and spices and fruits. p-Menth-3-en-9-al is found in fruits. p-Menth-3-en-9-al is a constituent of Spanish oregano (Coridothymus capitatus), Origanum species and blackberries

   

alpha-Terpineol formate

3-Cyclohexene-1-methanol, alpha,alpha,4-trimethyl-, formate

C11H18O2 (182.1306728)


alpha-Terpineol formate is found in cardamom. alpha-Terpineol formate is a flavouring agent Flavouring agent. alpha-Terpinyl formate is found in cardamom and sweet bay.

   

alpha-Terpineol propanoate

alpha,alpha,4-Trimethyl-3-cyclohexene-1-methyl propionate

C13H22O2 (210.1619712)


alpha-Terpineol propanoate is found in lemon. alpha-Terpineol propanoate is a flavouring agent Flavouring agent. alpha-Terpinyl propanoate is found in wild celery and lemon.

   

alpha-Terpineol butanoate

2-(4-Methylcyclohex-3-en-1-yl)propan-2-yl butanoic acid

C14H24O2 (224.1776204)


alpha-Terpineol butanoate is a flavouring agent Flavouring agent

   

alpha-Terpinyl pentanoate

2-(4-Methylcyclohex-3-en-1-yl)propan-2-yl pentanoic acid

C15H26O2 (238.1932696)


Alpha-Terpinyl pentanoate is a flavouring agent Prob. a flavouring agent

   

cis- and trans-L-Mercapto-p-menthan-3-one

5-Methyl-2-(propan-2-yl)-5-sulphanylcyclohexan-1-one

C10H18OS (186.1078298)


cis- and trans-L-Mercapto-p-menthan-3-one is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]") It is used as a food additive .

   

L-Menthyl acetoacetate

(1S,2R,5S)-5-Methyl-2-(propan-2-yl)cyclohexyl 3-oxobutanoic acid

C14H24O3 (240.1725354)


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

   

L-Menthyl (R,S)-3-hydroxybutyrate

(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 3-hydroxybutanoic acid

C14H26O3 (242.1881846)


L-Menthyl (R,S)-3-hydroxybutyrate is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]") It is used as a food additive .

   

1-Menthyl methyl ether

2-methoxy-4-methyl-1-(propan-2-yl)cyclohexane

C11H22O (170.1670562)


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

   

3-(L-Menthoxy)-2-methylpropane-1,2-diol

2-methyl-3-{[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}propane-1,2-diol

C14H28O3 (244.2038338)


3-(L-Menthoxy)-2-methylpropane-1,2-diol is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]") It is used as a food additive .

   

Terpinyl isobutyrate

2-(4-Methylcyclohex-3-en-1-yl)propan-2-yl 2-methylpropanoic acid

C14H24O2 (224.1776204)


alpha-Terpinyl isobutyrate is a flavouring ingredient with a heavy, fruity-type flavour. It is used as a food additive .

   

(1R,4R)-p-Mentha-2,8-dien-1-ol

(1R,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol

C10H16O (152.12010859999998)


(1R,4R)-p-Mentha-2,8-dien-1-ol is found in caraway. (1R,4R)-p-Mentha-2,8-dien-1-ol is isolated from gingergrass oil (Cymbopogon martini) and various Citrus oils. Metabolic and oxidation produced of Limonene JFH51-AJFH51-A. (1R,4R)-p-Mentha-2,8-dien-1-ol is found in caraway and citrus.

   

p-Menthan-2-one

Cyclohexanone, 2-methyl-5-(1-methylethyl)-

C10H18O (154.1357578)


p-Menthan-2-one is found in cornmint. p-Menthan-2-one is a flavouring ingredient. Flavouring ingredient. p-Menthan-2-one is found in cornmint.

   

(-)-Neoisomenthol

(1S,2S,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol

C10H20O (156.151407)


(-)-Neoisomenthol is found in herbs and spices. (-)-Neoisomenthol is isolated from geranium bourbon oil (Pelargonium roseum Isolated from geranium bourbon oil (Pelargonium roseum). (-)-Neoisomenthol is found in herbs and spices. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1]. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1]. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1].

   

(2S,4R)-p-Mentha-1(7),5-dien-2-ol acetate

2-Methylidene-5-(propan-2-yl)cyclohex-3-en-1-yl acetic acid

C12H18O2 (194.1306728)


(2S,4R)-p-Mentha-1(7),5-dien-2-ol acetate is found in fats and oils. (2S,4R)-p-Mentha-1(7),5-dien-2-ol acetate is a constituent of Angelica archangelica (angelica) Constituent of Angelica archangelica (angelica). (2S,4R)-p-Mentha-1(7),5-dien-2-ol acetate is found in fats and oils, herbs and spices, and green vegetables.

   

Carvone

2-Methyl-5-(1-methyl-1-ethenyl)-2-cyclohexen-1-one

C10H14O (150.1044594)


Carvone is found in anise. Carvone is a flavouring ingredient Flavouring ingredient. Constituent of gingergrass oil

   

alpha-Phellandrene

2-Methyl-5-(1-methylethyl)-1,3-cyclohexadiene

C10H16 (136.1251936)


Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. Phellandrene is found in many foods, some of which are ceylon cinnamon, peppermint, anise, and dill. alpha-Phellandrene is found in allspice. Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. alpha-Phellandrene and beta-phellandrene are cyclic monoterpenes and are double-bond isomers. The phellandrenes are used in fragrances because of their pleasing aromas. (Wikipedia

   

trans-(-)-p-Menth-1-en-3-ol

(1S,6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-ol

C10H18O (154.1357578)


trans-(-)-p-Menth-1-en-3-ol is found in herbs and spices. trans-(-)-p-Menth-1-en-3-ol is isolated from essential oils of Mentha and Eucalyptus specie Isolated from essential oils of Mentha and Eucalyptus subspecies trans-(-)-p-Menth-1-en-3-ol is found in mentha (mint) and herbs and spices.

   

(-)-Isopulegol

(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol

C10H18O (154.1357578)


Isolated from Mentha pulegium (European pennyroyal) and other essential oils. (-)-Isopulegol is found in many foods, some of which are lemon balm, lemon grass, rosemary, and fats and oils. (-)-Isopulegol is found in cornmint. (-)-Isopulegol is isolated from Mentha pulegium (European pennyroyal) and other essential oil

   

(R)-p-Mentha-1,8-dien-7-ol

[(4R)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol

C10H16O (152.12010859999998)


(R)-p-Mentha-1,8-dien-7-ol is found in herbs and spices. (R)-p-Mentha-1,8-dien-7-ol is isolated from caraway seed oi Isolated from caraway seed oil. (R)-p-Mentha-1,8-dien-7-ol is found in herbs and spices.

   

3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol

3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol

C13H26O3 (230.1881846)


3-[[5-Methyl-2-(1-methylethyl)cyclohexyl]oxy]-1,2-propanediol is a physiological cooling agent used in food and beverage Physiol. cooling agent used in food and beverages

   

Menthone 1,2-glyceryl ketal

9-Methyl-6-(1-methylethyl)-1,4-dioxaspiro[4.5]decane-2-methanol, 9ci

C13H24O3 (228.1725354)


Menthone 1,2-glyceryl ketal, also known as menthone glycerin acetal or menthyl glycerin acetal, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthone 1,2-glyceryl ketal is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Menthone 1,2-glyceryl ketal is used as a food additive (EAFUS: Everything Added to Food in the United States). Menthone 1,2-glyceryl ketal is a flavour enhancer for chewing gum and other low moisture foods. Flavour enhancer for chewing gum and other low moisture foods

   

Menthyl ethylene glycol carbonate

2-[({[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}carbonyl)oxy]ethan-1-ol

C13H24O4 (244.16745039999998)


Menthyl ethylene glycol carbonate is a physiological cooling agent used in foods. Strong mint flavorant used in chewing gu Physiol. cooling agent used in foods. Strong mint flavorant used in chewing gum

   

Monomenthyl succinate

4-{[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-4-oxobutanoic acid

C14H24O4 (256.1674504)


Monomenthyl succinate is a flavouring ingredient with a cooling, minty tast Flavouring ingredient with a cooling, minty taste

   

4-Isopropyl-3-cyclohexene-1-carboxylic acid

4-(1-Methylethyl)-3-cyclohexene-1-carboxylic acid, 9ci

C10H16O2 (168.1150236)


xi-4-Isopropyl-3-cyclohexene-1-carboxylic acid is found in herbs and spices. xi-4-Isopropyl-3-cyclohexene-1-carboxylic acid is a flavouring ingredient. xi-4-Isopropyl-3-cyclohexene-1-carboxylic acid is present in cumin oil. It is used as a food additive

   

Menthyl lactate

(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 2-hydroxypropanoic acid

C13H24O3 (228.1725354)


Menthyl lactate is a flavouring ingredient. Flavouring ingredient

   

trans-beta-Terpineol

(1s,4s)-1-methyl-4-(prop-1-en-2-yl)cyclohexan-1-ol

C10H18O (154.1357578)


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

   

p-Menth-1-en-9-ol acetate

3-Cyclohexene-1-ethanol, beta,4-dimethyl-, acetate

C12H20O2 (196.14632200000003)


p-Menth-1-en-9-ol acetate is found in mandarin orange (clementine, tangerine). p-Menth-1-en-9-ol acetate is a flavouring ingredient. Flavouring ingredient. p-Menth-1-en-9-ol acetate is found in spearmint.

   

Ethyl menthane carboxamide

N-Ethyl-5-methyl-2-(propan-2-yl)cyclohexane-1-carboximidate

C13H25NO (211.193604)


Physiological coolant used in foods, beverages, chewing gum, toiletries, topical pharmaceutical formulations and oral hygiene products. Physiological coolant used in foods, beverages, chewing gum, toiletries, topical pharmaceutical formulations and oral hygiene products

   

Carvyl propionate

2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl propanoic acid

C13H20O2 (208.14632200000003)


Carvyl propionate is a flavouring ingredient with a sweet, fruity, minty taste. Flavouring ingredient with a sweet, fruity, minty taste

   

p-Menth-3-ene-3-thiol

5-Methyl-2-(1-methylethyl)cyclohexanethione, 9ci

C10H18S (170.1129148)


p-Menth-3-ene-3-thiol is a flavouring ingredient. Flavouring ingredient

   

Menthadienyl acetate

2-Methylidene-5-(prop-1-en-2-yl)cyclohexyl acetic acid

C12H18O2 (194.1306728)


Menthadienyl acetate is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthadienyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Within the cell, menthadienyl acetate is primarily located in the membrane (predicted from logP). Menthadienyl acetate is a flavouring agent for candies.

   

Menthone 1,3-glyceryl ketal

10-Methyl-7-(1-methylethyl)-1,5-dioxaspiro[5.5]undecan-3-ol, 9ci

C13H24O3 (228.1725354)


Menthone 1,3-glyceryl ketal is a flavouring ingredient especially for chewing gum. Flavouring ingredient especies for chewing gum

   

Isopulegol acetate

Cyclohexanol,5-methyl-2-(1-methylethenyl)-, 1-acetate, (1R,2S,5R)-

C12H20O2 (196.14632200000003)


Isopulegol acetate is found in peppermint. Isopulegol acetate is a flavouring agent. Flavouring agent. (-)-Isopulegol acetate is found in peppermint.

   

Terpenyl isovalerate

2-(4-Methylcyclohex-3-en-1-yl)propan-2-yl 3-methylbutanoic acid

C15H26O2 (238.1932696)


Terpenyl isovalerate is a flavouring ingredient. Flavouring ingredient

   

Melongoside L

2-({6-[(3-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-2-{5,7,9,13-tetramethyl-5-oxaspiro[oxane-2,6-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]oxy}oxan-4-yl)oxy]-4,5-dihydroxy-2-methyloxan-3-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C57H94O27 (1210.5982174)


Melongoside L is found in fruits. Melongoside L is a constituent of aubergine (Solanum melongena).

   

(+)-Neoisomenthol

(1alpha,2alpha,5alpha)-5-methyl-2-(1-methylethyl)cyclohexanol

C10H20O (156.151407)


(+)-Neoisomenthol is found in many essential oils [CCD]. Found in many essential oils [CCD] DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1]. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1]. DL-Menthol is a relative configuration of (-)-Menthol. DL-Menthol relates to the activation of GABAA receptor[1].

   

Carvotanacetone

(5S)-2-methyl-5-(propan-2-yl)cyclohex-2-en-1-one

C10H16O (152.12010859999998)


Carvotanacetone belongs to the family of Monocyclic Monoterpenes. These are monoterpenes containing 1 ring in the isoprene chain

   

2-Hydroxypropyl 2-isopropyl-5-methylcyclohexyl carbonate

1-[({[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}carbonyl)oxy]propan-2-ol

C14H26O4 (258.1830996)


2-Hydroxypropyl 2-isopropyl-5-methylcyclohexyl carbonate belongs to the family of Monocyclic Monoterpenes. These are monoterpenes containing 1 ring in the isoprene chain

   

1-Hydroxypropan-2-yl 2-isopropyl-5-methylcyclohexyl carbonate

2-[({[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}carbonyl)oxy]propan-1-ol

C14H26O4 (258.1830996)


1-Hydroxypropan-2-yl 2-isopropyl-5-methylcyclohexyl carbonate belongs to the family of Monocyclic Monoterpenes. These are monoterpenes containing 1 ring in the isoprene chain.

   

1,1,2-Trimethyl-3,5-bis(1-methylethenyl)cyclohexane

1,1,2-Trimethyl-3,5-bis(1-methylethenyl)cyclohexane

C15H26 (206.2034396)


1,1,2-Trimethyl-3,5-bis(1-methylethenyl)cyclohexane belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

   

2-Menthene

(3R,6R)-3-methyl-6-(propan-2-yl)cyclohex-1-ene

C10H18 (138.1408428)


2-Menthene belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

   

5-Methyl-2-(1-methylethyl)-cyclohexanone

(2R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one

C10H18O (154.1357578)


5-Methyl-2-(1-methylethyl)-cyclohexanone belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

   

4-Methyl-2-methylene-1-(1methylethylidene)-cyclohexane

4-Methyl-2-methylene-1-(1methylethylidene)-cyclohexane

C11H18 (150.1408428)


4-Methyl-2-methylene-1-(1methylethylidene)-cyclohexane belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

   

1-Acetyl-2-methylcyclopentene

1,2-dimethyl-3,5-bis(prop-1-en-2-yl)cyclohexane

C14H24 (192.18779039999998)


1-Acetyl-2-methylcyclopentene belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

   

1S,2S,5R-1,4,4 Trimethyltricyclo[6.3.1.0(2,5)]dodec-8(9)- ene

1S,2S,5R-1,4,4 Trimethyltricyclo[6.3.1.0(2,5)]dodec-8(9)- ene

C15H24 (204.18779039999998)


1S,2S,5R-1,4,4 Trimethyltricyclo[6.3.1.0(2,5)]dodec-8(9)- ene belongs to the class of organic compounds known as polycyclic hydrocarbons. These are polycyclic organic compounds made up only of carbon and hydrogen atoms.

   

(-)-Menthyl chloroformate

5-methyl-2-(propan-2-yl)cyclohexyl chloroformate

C11H19ClO2 (218.1073504)


   

Dihydroperillic acid

4-(1-Methylethenyl)cyclohexane-1-carboxylic acid

C10H16O2 (168.1150236)


   

1-Methylene-4-(1-methylvinyl)cyclohexane

1-methylidene-4-(prop-1-en-2-yl)cyclohexane

C10H16 (136.1251936)


   

Sobrepin

5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-en-1-ol

C10H18O2 (170.1306728)


   

p-Menth-4(8)-en-3-ol

(1R,5R)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-ol

C10H18O (154.1357578)


P-menth-4(8)-en-3-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. P-menth-4(8)-en-3-ol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). P-menth-4(8)-en-3-ol can be found in spearmint, which makes P-menth-4(8)-en-3-ol a potential biomarker for the consumption of this food product.

   

Isopiperitenone

3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-one

C10H14O (150.1044594)


Isopiperitenone, also known as 3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-one or 6-isopropenyl-3-methyl-2-cyclohexen-1-one, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Isopiperitenone is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Isopiperitenone can be found in dill and spearmint, which makes isopiperitenone a potential biomarker for the consumption of these food products.

   

(E)-8(9)-p-Menthen-1,2-diol

(1R,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol

C10H18O2 (170.1306728)


(e)-8(9)-p-menthen-1,2-diol is soluble (in water) and a very weakly acidic compound (based on its pKa). (e)-8(9)-p-menthen-1,2-diol can be found in wild celery, which makes (e)-8(9)-p-menthen-1,2-diol a potential biomarker for the consumption of this food product.

   

cis-Carvyl acetate

(1S,5S)-2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl acetic acid

C12H18O2 (194.1306728)


Cis-carvyl acetate is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Cis-carvyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cis-carvyl acetate can be found in spearmint and wild celery, which makes cis-carvyl acetate a potential biomarker for the consumption of these food products.

   

Dihydroisocarveol

(1R,2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol

C10H18O (154.1357578)


(-)-dihydrocarveol, also known as (1r,2r,5r)-5-isopropenyl-2-methylcyclohexanol or (1r,2r,4r)-P-menth-8-en-2-ol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (-)-dihydrocarveol is considered to be an isoprenoid lipid molecule (-)-dihydrocarveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). (-)-dihydrocarveol can be found in fats and oils and herbs and spices, which makes (-)-dihydrocarveol a potential biomarker for the consumption of these food products.

   

trans-Carvyl acetate

(1S,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl acetate

C12H18O2 (194.1306728)


Trans-carvyl acetate is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Trans-carvyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Trans-carvyl acetate can be found in spearmint and wild celery, which makes trans-carvyl acetate a potential biomarker for the consumption of these food products.

   

trans-p-Mentha-1(7),8-dien-2-ol

(1S,5S)-2-methylidene-5-(prop-1-en-2-yl)cyclohexan-1-ol

C10H16O (152.12010859999998)


Trans-p-mentha-1(7),8-dien-2-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Trans-p-mentha-1(7),8-dien-2-ol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Trans-p-mentha-1(7),8-dien-2-ol can be found in wild celery, which makes trans-p-mentha-1(7),8-dien-2-ol a potential biomarker for the consumption of this food product.

   

trans-p-Mentha-2,8-dien-1-ol

(1S,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol

C10H16O (152.12010859999998)


Trans-p-mentha-2,8-dien-1-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Trans-p-mentha-2,8-dien-1-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Trans-p-mentha-2,8-dien-1-ol is a fresh and minty tasting compound found in spearmint and wild celery, which makes trans-p-mentha-2,8-dien-1-ol a potential biomarker for the consumption of these food products.

   

1-p-Menthene-6-ol

2-Methyl-5-(1-methylethyl)-2-cyclohexen-1-ol

C10H18O (154.1357578)


1-p-menthene-6-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 1-p-menthene-6-ol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). 1-p-menthene-6-ol can be found in caraway, which makes 1-p-menthene-6-ol a potential biomarker for the consumption of this food product.

   

2,8-p-Menthadien-6-ol

2-methyl-5-(prop-1-en-2-yl)cyclohex-3-en-1-ol

C10H16O (152.12010859999998)


2,8-p-menthadien-6-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 2,8-p-menthadien-6-ol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). 2,8-p-menthadien-6-ol can be found in caraway, which makes 2,8-p-menthadien-6-ol a potential biomarker for the consumption of this food product.

   

8-cis-Menthene

(1s,4s)-1-methyl-4-(prop-1-en-2-yl)cyclohexane

C10H18 (138.1408428)


8-cis-menthene is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 8-cis-menthene can be found in caraway, which makes 8-cis-menthene a potential biomarker for the consumption of this food product.

   

D-Perillaldehyde

(4R)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde

C10H14O (150.1044594)


Perillaldehyde or perillyl aldehyde belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. 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-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. p-Menthane consists of a cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Perillyl aldehyde is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Perillaldehyde is a cherry, and fatty tasting compound found in herbs and spices. It is a natural organic compound found most abundantly in the annual herb perilla, but also in a wide variety of other plants and essential oils. Perillaldehyde, or volatile oils from perilla that are rich in perillaldehyde, are used as food additives for flavoring and in perfumery to add spiciness. Perillaldehyde can be readily converted to perilla alcohol, which is also used in perfumery. It has a mint-like, cinnamon odor and is primarily responsible for the flavor of perilla. D-perillaldehyde is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. D-perillaldehyde is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). D-perillaldehyde can be found in caraway, which makes D-perillaldehyde a potential biomarker for the consumption of this food product. Perillaldehyde, or volatile oils from perilla that are rich in perillaldehyde, are used as food additives for flavoring and in perfumery to add spiciness. Perillaldehyde can be readily converted to perilla alcohol, which is also used in perfumery. It has a mint-like, cinnamon odor and is primarily responsible for the flavor of perilla .

   

Anthemol

[4-(propan-2-yl)cyclohexa-1,3-dien-1-yl]methanol

C10H16O (152.12010859999998)


Anthemol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Anthemol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Anthemol can be found in roman camomile, which makes anthemol a potential biomarker for the consumption of this food product.

   

p-Mentha-1,3-dien-7-al

4-(propan-2-yl)cyclohexa-1,3-diene-1-carbaldehyde

C10H14O (150.1044594)


P-mentha-1,3-dien-7-al is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. P-mentha-1,3-dien-7-al is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). P-mentha-1,3-dien-7-al is a fat, fatty, and spice tasting compound found in cumin, which makes P-mentha-1,3-dien-7-al a potential biomarker for the consumption of this food product.

   

p-Mentha-3-en-7-ol

[4-(propan-2-yl)cyclohex-3-en-1-yl]methanol

C10H18O (154.1357578)


P-mentha-3-en-7-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. P-mentha-3-en-7-ol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). P-mentha-3-en-7-ol can be found in cumin, which makes P-mentha-3-en-7-ol a potential biomarker for the consumption of this food product.

   

cis-p-Menth-2-en-1-ol

(1S,4R)-1-methyl-4-(propan-2-yl)cyclohex-2-en-1-ol

C10H18O (154.1357578)


Cis-p-menth-2-en-1-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Cis-p-menth-2-en-1-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Cis-p-menth-2-en-1-ol can be found in cardamom, sweet bay, and sweet marjoram, which makes cis-p-menth-2-en-1-ol a potential biomarker for the consumption of these food products.

   

p-Menth-cis-2-en-1-ol

1-methyl-4-(propan-2-yl)cyclohex-2-en-1-ol

C10H18O (154.1357578)


P-menth-cis-2-en-1-ol, also known as quercivorol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. P-menth-cis-2-en-1-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). P-menth-cis-2-en-1-ol can be found in a number of food items such as cardamom, rosemary, spearmint, and nutmeg, which makes P-menth-cis-2-en-1-ol a potential biomarker for the consumption of these food products.

   

p-Menthene

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

C10H18 (138.1408428)


P-menthene is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. P-menthene can be found in cardamom, which makes P-menthene a potential biomarker for the consumption of this food product.

   

trans-p-Menth-2-en-1-ol

(1R,4R)-1-methyl-4-(propan-2-yl)cyclohex-2-en-1-ol

C10H18O (154.1357578)


Trans-p-menth-2-en-1-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Trans-p-menth-2-en-1-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Trans-p-menth-2-en-1-ol is a herb tasting compound found in cardamom and sweet marjoram, which makes trans-p-menth-2-en-1-ol a potential biomarker for the consumption of these food products.

   

Pulegol

5-methyl-2-(propan-2-ylidene)cyclohexan-1-ol

C10H18O (154.1357578)


Pulegol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Pulegol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Pulegol can be found in lemon balm, which makes pulegol a potential biomarker for the consumption of this food product.

   

(+)-8-Acetoxycarvone

(1R)-4-Methyl-5-oxo-1-(prop-1-en-2-yl)cyclohex-3-en-1-yl acetic acid

C12H16O3 (208.1099386)


(+)-8-acetoxycarvone is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (+)-8-acetoxycarvone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (+)-8-acetoxycarvone can be found in cornmint, which makes (+)-8-acetoxycarvone a potential biomarker for the consumption of this food product.

   

p-Menthan-trans-2,5-diol

(2R,5R)-2-methyl-5-(propan-2-yl)cyclohexane-1,4-diol

C10H20O2 (172.14632200000003)


P-menthan-trans-2,5-diol is soluble (in water) and a very weakly acidic compound (based on its pKa). P-menthan-trans-2,5-diol can be found in cornmint, which makes P-menthan-trans-2,5-diol a potential biomarker for the consumption of this food product.

   

5-Hydroxycarvone

6-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one

C10H14O2 (166.09937440000002)


5-hydroxycarvone is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 5-hydroxycarvone is soluble (in water) and a very weakly acidic compound (based on its pKa). 5-hydroxycarvone can be found in spearmint, which makes 5-hydroxycarvone a potential biomarker for the consumption of this food product.

   

1-Menthol acetate

Cyclohexanol, 1-methyl-4-(1-methylethyl)-, acetate

C12H22O2 (198.1619712)


1-menthol acetate is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 1-menthol acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 1-menthol acetate can be found in spearmint, which makes 1-menthol acetate a potential biomarker for the consumption of this food product.

   

p-Menth-trans-2,8-dien-1-ol

1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol

C10H16O (152.12010859999998)


P-mentha-2,8-dien-1-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. P-mentha-2,8-dien-1-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). P-mentha-2,8-dien-1-ol can be found in a number of food items such as caraway, pepper (spice), lemon, and wild celery, which makes P-mentha-2,8-dien-1-ol a potential biomarker for the consumption of these food products.

   

trans-Carvyl formate

(1R,5S)-2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl formic acid

C11H16O2 (180.1150236)


Trans-carvyl formate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Trans-carvyl formate can be found in spearmint, which makes trans-carvyl formate a potential biomarker for the consumption of this food product.

   

cis-p-Menth-1-en-3-ol

(1R,6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-ol

C10H18O (154.1357578)


Cis-p-menth-1-en-3-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Cis-p-menth-1-en-3-ol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Cis-p-menth-1-en-3-ol is a herbal tasting compound and can be found in a number of food items such as common oregano, nutmeg, peppermint, and rosemary, which makes cis-p-menth-1-en-3-ol a potential biomarker for the consumption of these food products.

   

Isomenthol acetate

(1R,2S,5S)-5-Methyl-2-(propan-2-yl)cyclohexyl acetic acid

C12H22O2 (198.1619712)


Isomenthol acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Isomenthol acetate can be found in peppermint and spearmint, which makes isomenthol acetate a potential biomarker for the consumption of these food products.

   

Neoisomenthol acetate

(1R,2R,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl acetic acid

C12H22O2 (198.1619712)


Neoisomenthol acetate is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Neoisomenthol acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Neoisomenthol acetate can be found in peppermint, which makes neoisomenthol acetate a potential biomarker for the consumption of this food product.

   

1-Ethoxy-p-menth-2-ene

3-ethoxy-3-methyl-6-(propan-2-yl)cyclohex-1-ene

C12H22O (182.1670562)


1-ethoxy-p-menth-2-ene is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 1-ethoxy-p-menth-2-ene is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 1-ethoxy-p-menth-2-ene can be found in sweet marjoram, which makes 1-ethoxy-p-menth-2-ene a potential biomarker for the consumption of this food product.

   

4-Ethoxy-p-menth-1-ene

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

C12H22O (182.1670562)


4-ethoxy-p-menth-1-ene is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 4-ethoxy-p-menth-1-ene is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 4-ethoxy-p-menth-1-ene can be found in sweet marjoram, which makes 4-ethoxy-p-menth-1-ene a potential biomarker for the consumption of this food product.

   

cis-3-Ethoxy-p-menth-1-ene

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

C12H22O (182.1670562)


Cis-3-ethoxy-p-menth-1-ene is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Cis-3-ethoxy-p-menth-1-ene is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cis-3-ethoxy-p-menth-1-ene can be found in sweet marjoram, which makes cis-3-ethoxy-p-menth-1-ene a potential biomarker for the consumption of this food product.

   

cis-p-Menth-2-enol

3-methyl-6-(propan-2-yl)cyclohex-1-en-1-ol

C10H18O (154.1357578)


Cis-p-menth-2-enol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Cis-p-menth-2-enol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cis-p-menth-2-enol can be found in sweet marjoram, which makes cis-p-menth-2-enol a potential biomarker for the consumption of this food product.

   

Terpinenol

5-methyl-2-(propan-2-yl)cyclohex-1-en-1-ol

C10H18O (154.1357578)


Terpinenol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Terpinenol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Terpinenol can be found in sweet marjoram, which makes terpinenol a potential biomarker for the consumption of this food product.

   

1,8-Menthadien-2-ol

2-methyl-5-(prop-1-en-2-yl)cyclohex-1-en-1-ol

C10H16O (152.12010859999998)


1,8-menthadien-2-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 1,8-menthadien-2-ol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 1,8-menthadien-2-ol can be found in pepper (spice), which makes 1,8-menthadien-2-ol a potential biomarker for the consumption of this food product.

   

3,8(9)-p-Menthadien-1-ol

(1R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-3-en-1-ol

C10H16O (152.12010859999998)


3,8(9)-p-menthadien-1-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 3,8(9)-p-menthadien-1-ol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). 3,8(9)-p-menthadien-1-ol can be found in pepper (spice), which makes 3,8(9)-p-menthadien-1-ol a potential biomarker for the consumption of this food product.

   

cis-2,8-Menthadien-2-ol

6-methyl-3-(prop-1-en-2-yl)cyclohex-1-en-1-ol

C10H16O (152.12010859999998)


Cis-2,8-menthadien-2-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Cis-2,8-menthadien-2-ol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Cis-2,8-menthadien-2-ol can be found in pepper (spice), which makes cis-2,8-menthadien-2-ol a potential biomarker for the consumption of this food product.

   

(-)-trans-Isomenth-5-en-2-ol

(1S,2S,5S)-2-methyl-5-(propan-2-yl)cyclohex-3-en-1-ol

C10H18O (154.1357578)


(-)-trans-isomenth-5-en-2-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (-)-trans-isomenth-5-en-2-ol can be found in corn, which makes (-)-trans-isomenth-5-en-2-ol a potential biomarker for the consumption of this food product.

   

p-Mentha-1,5-dien-7-ol

[4-(propan-2-yl)cyclohexa-1,5-dien-1-yl]methanol

C10H16O (152.12010859999998)


P-mentha-1,5-dien-7-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. P-mentha-1,5-dien-7-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). P-mentha-1,5-dien-7-ol can be found in ginger, which makes P-mentha-1,5-dien-7-ol a potential biomarker for the consumption of this food product.

   

(+/-)-cis- and trans-1,2-Dihydroperillaldehyde

(+/-)-cis- and trans-1,2-Dihydroperillaldehyde

C10H16O (152.12010859999998)


It is used as a food additive .

   

2-(L-Menthoxy)ethanol

2-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}ethan-1-ol

C12H24O2 (200.1776204)


It is used as a food additive .

   

Menthyl valerate

5-methyl-2-(propan-2-yl)cyclohexyl pentanoate

C15H28O2 (240.20891880000002)


Menthyl valerate, also known as menthyl valeric acid, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthyl valerate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Menthyl valerate is a mild, sweet, and fruity tasting compound found in orange mint and peppermint, which makes menthyl valerate a potential biomarker for the consumption of these food products.

   

L-Monomenthyl glutarate

5-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-5-oxopentanoic acid

C15H26O4 (270.1830996)


It is used as a food additive .

   

(R)-Menthone 8-thioacetate

(2R,5S)-2-[2-(acetylsulfanyl)propan-2-yl]-5-methylcyclohexan-1-one

C12H20O2S (228.11839400000002)


Flavour ingredient for various formulations (as mixture with the trans-form). Present in Buchu leaf oil

   

(±)-Isomenthol

(1R,2S,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol

C10H20O (156.151407)


(±)-isomenthol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (±)-isomenthol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (±)-isomenthol can be found in a number of food items such as cabbage, peppermint, sunflower, and white cabbage, which makes (±)-isomenthol a potential biomarker for the consumption of these food products.

   

(+)-Neoisopulegol

(1S,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol

C10H18O (154.1357578)


(+)-neoisopulegol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (+)-neoisopulegol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). (+)-neoisopulegol can be found in ginger, peppermint, and spearmint, which makes (+)-neoisopulegol a potential biomarker for the consumption of these food products.

   

dihydroterpinyl acetate

2-(4-Methylcyclohexyl)propan-2-yl acetic acid

C12H22O2 (198.1619712)


Flavouring compound [Flavornet]

   

p-mentha-1,8-dien-4-yl-hydroperoxide

4-methylidene-1-(prop-1-en-2-yl)cyclohexane-1-peroxol

C10H16O2 (168.1150236)


Flavouring compound [Flavornet]

   

(E)-p-mentha-1(7),8-dien-2-hydroperoxide

(1R,5S)-2-methylidene-5-(prop-1-en-2-yl)cyclohexane-1-peroxol

C10H16O2 (168.1150236)


Flavouring compound [Flavornet]

   

(E)-p-mentha-6,8-dien-2-hydroperoxide

2-methyl-5-(prop-1-en-2-yl)cyclohex-1-ene-1-peroxol

C10H16O2 (168.1150236)


Flavouring compound [Flavornet]

   

(Z)-p-mentha-1,8-dien-2-hydroperoxide

2-methylidene-5-(prop-1-en-2-yl)cyclohexane-1-peroxol

C10H16O2 (168.1150236)


Flavouring compound [Flavornet]

   

DL-Menthyl acetate

5-Methyl-2-(propan-2-yl)cyclohexyl acetic acid

C12H22O2 (198.1619712)


Flavouring compound [Superscent]