(-)-Sabinene

(1R,5R)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexane (1R,5R)-thuj-4(10)-ene

C10H16 (136.1252)


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

   

Pulegone

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

C10H16O (152.1201)


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

   

(-)-Menthone

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 (154.1358)


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

   

beta-Phellandrene

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

C10H16 (136.1252)


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

   

p-Cymene

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

C10H14 (134.1095)


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

   

Terpinolene

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

C10H16 (136.1252)


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

   

Ascaridole

1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene, 9ci

C10H16O2 (168.115)


Ascaridole is found in cardamom. Said to be the major constituent of oil of Peumus boldus (boldo).Ascaridole is a natural organic compound classified as a bicyclic monoterpene that has an unusual bridging peroxide functional group. It is the primary constituent of the oil of Mexican Tea (Dysphania ambrosioides, formerly Chenopodium ambrosioides). It is a colorless liquid that is soluble in most organic solvents. Like other low molecular weight organic peroxides, it is unstable and prone to explosion when heated or treated with organic acids Said to be the major constituent of oil of Peumus boldus (boldo) D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides

   

(+)-beta-Phellandrene

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

C10H16 (136.1252)


(+)-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.

   

fusicocca-2,10(14)-diene

3-Isopropyl-6,9,10a-trimethyl-1,2,4,5,6,6a,7,8,10,10a-decahydrodicyclopenta[a,d]cyclooctene

C20H32 (272.2504)


   

Gurjunene-alpha

(1aR,4R,4aR,7bS)-1,1,4,7-tetramethyl-1H,1aH,2H,3H,4H,4aH,5H,6H,7bH-cyclopropa[e]azulene

C15H24 (204.1878)


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

   

(+)-Limonene

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

C10H16 (136.1252)


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

   

Isomenthone

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

C10H18O (154.1358)


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

   

(+)-Menthone

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

C10H18O (154.1358)


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

   

(-)-beta-Phellandrene

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

C10H16 (136.1252)


(-)-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).

   

iso-Mentone

(±)-Isomenthone

C10H18O (154.1358)


Flavouring ingredient. (±)-Isomenthone is found in many foods, some of which are blackcurrant, orange mint, peppermint, and spearmint. (+)-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].

   

Spathulenol

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

C15H24O (220.1827)


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

   

Pulegone

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

C10H16O (152.1201)


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

   

1-Octen-3-yl acetate

Pentyl vinyl carbinol acetate

C10H18O2 (170.1307)


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

   

Menthone

Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5S)-rel-

C10H18O (154.1358)


P-menthan-3-one is a p-menthane monoterpenoid that is p-menthane substituted by an oxo group at position 3. It has a role as a plant metabolite and a volatile oil component. p-Menthan-3-one is a natural product found in Citrus hystrix, Mentha aquatica, and other organisms with data available. The trans-stereoisomer of p-menthan-3-one. Flavouring compound [Flavornet] (-)-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].

   

3-Methoxybibenzyl-3,4-diol

3-Methoxybibenzyl-3,4-diol

C15H16O3 (244.1099)


   

4-[2-(4-methoxyphenyl)ethyl]phenol

4-[2-(4-methoxyphenyl)ethyl]phenol

C15H16O2 (228.115)


   

iso-Mentone

(+)-Isomenthone; (2R,5R)-2-Isopropyl-5-methyl-cyclohexanone

C10H18O (154.1358)


(+)-isomenthone is an isomenthone. It is an enantiomer of a (-)-isomenthone. (+)-Isomenthone is a natural product found in Myrtus communis, Cornus officinalis, and other organisms with data available. (+)-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].

   

Sabinene

Bicyclo[3.1.0]hexane, 4-methylene-1-(1-methylethyl)-

C10H16 (136.1252)


Sabinene is a thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species. It has a role as a plant metabolite. Black pepper allergenic extract is used in allergenic testing. Laurus nobilis allergenic extract is used in allergenic testing. Nutmeg allergenic extract is used in allergenic testing. Sabinene is a natural product found in Teucrium montanum, Xylopia aromatica, and other organisms with data available. Carrot Seed Oil is the oil extracted from the seeds of Daucus carota. Carrot seed oil is primarily used in skin treatment preparations. A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species. 4(10)-thujene, also known as sabinen or 1-isopropyl-4-methylenebicyclo[3.1.0]hexane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. 4(10)-thujene is a citrus, pepper, and pine tasting compound and can be found in a number of food items such as sweet orange, green bell pepper, pot marjoram, and parsley, which makes 4(10)-thujene a potential biomarker for the consumption of these food products. Sabinene is an naturally occurring bicyclic monoterpene which can be used as flavorings, perfume additives, fine chemicals, and advanced biofuels. Sabinene is also an orally active compound to attenuates skeletal muscle atrophy and regulates ROS-mediated MAPK/MuRF-1 pathways[1][2]. Sabinene is an naturally occurring bicyclic monoterpene which can be used as flavorings, perfume additives, fine chemicals, and advanced biofuels. Sabinene is also an orally active compound to attenuates skeletal muscle atrophy and regulates ROS-mediated MAPK/MuRF-1 pathways[1][2].

   

Octenyl acetate

Pentyl vinyl carbinol acetate

C10H18O2 (170.1307)


   

p-Menthone

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

C10H18O (154.1358)


A menthone that is cyclohexanone substituted by a methyl and an isopropyl group at positions 5 and 2 respectively (the 2R,5S-stereoisomer).

   

β-Phellandrene

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

C10H16 (136.1252)


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].

   

L-beta-Phellandrene

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

C10H16 (136.1252)


   

P-CYMENE

P-CYMENE

C10H14 (134.1095)


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

   

Terpinolen

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

C10H16 (136.1252)


   

4-[2-(3-Hydroxyphenyl)ethyl]-2-[4-[2-(3-hydroxyphenyl)ethyl]phenoxy]phenol

4-[2-(3-Hydroxyphenyl)ethyl]-2-[4-[2-(3-hydroxyphenyl)ethyl]phenoxy]phenol

C28H26O4 (426.1831)


   

Cymol

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

C10H14 (134.1095)


   

Tereben

Dipentene Fluka specially purified fraction of terpene hydrocarbons

C10H16 (136.1252)


   

CHEBI:36492

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

C10H18O (154.1358)


(+)-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].

   

CHEBI:31

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

C10H18O (154.1358)


   

(1S,2E,10R)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene

(1S,2E,10R)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene

C15H24 (204.1878)


   

ORANGE TERPENES

ORANGE TERPENES

C10H16 (136.1252)


   

TERPINOLENE

TERPINOLENE

C10H16 (136.1252)


A p-menthadiene with double bonds at positions 1 and 4(8).

   

isomenthone

Isomenthone, (+/-)-

C10H18O (154.1358)


   

ASCARIDOLE

ASCARIDOLE

C10H16O2 (168.115)


A p-menthane monoterpenoid that is p-menth-2-ene with a peroxy group across position 1 to 4. D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides

   

1-Octen-3-yl acetate

1-Octen-3-yl acetate

C10H18O2 (170.1307)


   

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

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

C15H24 (204.1878)


   

(1'r,3r,3as,4's,4as,6'r,7'r,8's,8as,9as,11's,13'r)-6'-hydroxy-7'-isopropyl-1',4',5,8a,11'-pentamethyl-4,4a,7,8,9,9a-hexahydro-3ah-spiro[naphtho[2,3-b]furan-3,15'-tetracyclo[11.2.1.0²,¹².0⁴,⁸]hexadecan]-2'(12')-en-2-one

(1'r,3r,3as,4's,4as,6'r,7'r,8's,8as,9as,11's,13'r)-6'-hydroxy-7'-isopropyl-1',4',5,8a,11'-pentamethyl-4,4a,7,8,9,9a-hexahydro-3ah-spiro[naphtho[2,3-b]furan-3,15'-tetracyclo[11.2.1.0²,¹².0⁴,⁸]hexadecan]-2'(12')-en-2-one

C35H52O3 (520.3916)


   

(1'r,3r,3ar,4'r,7'r,8's,8ar,9ar,11's,13'r)-7'-isopropyl-1',4',5,8a,11'-pentamethyl-4,6,7,8,9,9a-hexahydro-3ah-spiro[naphtho[2,3-b]furan-3,15'-tetracyclo[11.2.1.0²,¹².0⁴,⁸]hexadecan]-2'(12')-en-2-one

(1'r,3r,3ar,4'r,7'r,8's,8ar,9ar,11's,13'r)-7'-isopropyl-1',4',5,8a,11'-pentamethyl-4,6,7,8,9,9a-hexahydro-3ah-spiro[naphtho[2,3-b]furan-3,15'-tetracyclo[11.2.1.0²,¹².0⁴,⁸]hexadecan]-2'(12')-en-2-one

C35H52O2 (504.3967)


   

(1ar,3as,7s,7as,7br)-1,1,3a,7-tetramethyl-octahydrocyclopropa[a]naphthalen-7-ol

(1ar,3as,7s,7as,7br)-1,1,3a,7-tetramethyl-octahydrocyclopropa[a]naphthalen-7-ol

C15H26O (222.1984)


   

(1r,2s,4r)-3,3,7,11-tetramethyltetracyclo[5.4.0.0¹,⁸.0²,⁴]undec-10-ene

(1r,2s,4r)-3,3,7,11-tetramethyltetracyclo[5.4.0.0¹,⁸.0²,⁴]undec-10-ene

C15H22 (202.1721)


   

4-[2-(3-methoxyphenyl)ethyl]phenol

4-[2-(3-methoxyphenyl)ethyl]phenol

C15H16O2 (228.115)


   

4-[2-(3-hydroxyphenyl)ethyl]-2-{4-[2-(3-hydroxyphenyl)ethyl]phenoxy}phenol

4-[2-(3-hydroxyphenyl)ethyl]-2-{4-[2-(3-hydroxyphenyl)ethyl]phenoxy}phenol

C28H26O4 (426.1831)


   

(7ar)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol

(7ar)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol

C15H24O (220.1827)


   

(-)-chamigrene

(-)-chamigrene

C15H24 (204.1878)


   

(1'r,3r,3ar,4'r,4ar,7'r,8's,8ar,9ar,11's,13'r)-7'-isopropyl-1',4',5,8a,11'-pentamethyl-4,4a,7,8,9,9a-hexahydro-3ah-spiro[naphtho[2,3-b]furan-3,15'-tetracyclo[11.2.1.0²,¹².0⁴,⁸]hexadecan]-2'(12')-en-2-one

(1'r,3r,3ar,4'r,4ar,7'r,8's,8ar,9ar,11's,13'r)-7'-isopropyl-1',4',5,8a,11'-pentamethyl-4,4a,7,8,9,9a-hexahydro-3ah-spiro[naphtho[2,3-b]furan-3,15'-tetracyclo[11.2.1.0²,¹².0⁴,⁸]hexadecan]-2'(12')-en-2-one

C35H52O2 (504.3967)


   

4-[2-(3-methoxyphenyl)ethyl]benzene-1,2-diol

4-[2-(3-methoxyphenyl)ethyl]benzene-1,2-diol

C15H16O3 (244.1099)


   

(3as,7s)-7-hydroxy-1,1,3a,7-tetramethyl-hexahydro-1ah-cyclopropa[a]naphthalen-4-one

(3as,7s)-7-hydroxy-1,1,3a,7-tetramethyl-hexahydro-1ah-cyclopropa[a]naphthalen-4-one

C15H24O2 (236.1776)


   

(1's,2's,3r,3as,5's,7'r,8as,9as,10'r)-2',5,6',6',8a,9'-hexamethyl-4,6,7,8,9,9a-hexahydro-3ah-spiro[naphtho[2,3-b]furan-3,12'-tetracyclo[8.2.1.0¹,⁸.0⁵,⁷]tridecan]-8'-en-2-one

(1's,2's,3r,3as,5's,7'r,8as,9as,10'r)-2',5,6',6',8a,9'-hexamethyl-4,6,7,8,9,9a-hexahydro-3ah-spiro[naphtho[2,3-b]furan-3,12'-tetracyclo[8.2.1.0¹,⁸.0⁵,⁷]tridecan]-8'-en-2-one

C30H42O2 (434.3185)


   

(1s,7r,8r)-12-isopropyl-1,4,8-trimethyltricyclo[9.3.0.0³,⁷]tetradeca-3,11-diene

(1s,7r,8r)-12-isopropyl-1,4,8-trimethyltricyclo[9.3.0.0³,⁷]tetradeca-3,11-diene

C20H32 (272.2504)


   

2-methoxy-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol

2-methoxy-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol

C12H16O3 (208.1099)


   

3-[2-(4-methoxyphenyl)ethyl]phenol

3-[2-(4-methoxyphenyl)ethyl]phenol

C15H16O2 (228.115)


   

1,3,4,6,6-pentamethyl-2-oxatricyclo[5.3.1.0³,⁸]undecane

1,3,4,6,6-pentamethyl-2-oxatricyclo[5.3.1.0³,⁸]undecane

C15H26O (222.1984)


   
   

[(1r,2s,4s,8r,9r)-9-(acetyloxy)-3,3-dimethyl-7-methylidene-10-oxatricyclo[6.4.0.0²,⁴]dodec-11-en-12-yl]methyl acetate

[(1r,2s,4s,8r,9r)-9-(acetyloxy)-3,3-dimethyl-7-methylidene-10-oxatricyclo[6.4.0.0²,⁴]dodec-11-en-12-yl]methyl acetate

C19H26O5 (334.178)


   

(4r)-4-[(1r)-1,2-dimethylcyclopent-2-en-1-yl]-1,4-dimethylcyclohex-1-ene

(4r)-4-[(1r)-1,2-dimethylcyclopent-2-en-1-yl]-1,4-dimethylcyclohex-1-ene

C15H24 (204.1878)


   

(7e)-14-oxapentacyclo[21.3.1.1²,⁶.1⁹,¹³.0¹⁵,²⁰]nonacosa-1(27),2(29),3,5,7,9,11,13(28),15,17,19,23,25-tridecaene-3,18,26-triol

(7e)-14-oxapentacyclo[21.3.1.1²,⁶.1⁹,¹³.0¹⁵,²⁰]nonacosa-1(27),2(29),3,5,7,9,11,13(28),15,17,19,23,25-tridecaene-3,18,26-triol

C28H22O4 (422.1518)


   

(1as,4as,7s,7ar,7bs)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol

(1as,4as,7s,7ar,7bs)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol

C15H24O (220.1827)


   

(1s,4s)-1-isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene

(1s,4s)-1-isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene

C10H16O2 (168.115)