NCBI Taxonomy: 1945650

Micromeria maderensis (ncbi_taxid: 1945650)

found 99 associated metabolites at species taxonomy rank level.

Ancestor: Micromeria

Child Taxonomies: none taxonomy data.

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

Linalool, certified reference material, TraceCERT(R)

C10H18O (154.1358)


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

   

beta-Elemene

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

C15H24 (204.1878)


(-)-beta-elemene is the (-)-enantiomer of beta-elemene that has (1S,2S,4R)-configuration. It has a role as an antineoplastic agent. beta-Elemene is a natural product found in Xylopia sericea, Eupatorium cannabinum, and other organisms with data available. Beta-elemene is one of the isomers of elemene, a lipid soluble sesquiterpene and the active component isolated from the Chinese medicinal herb Rhizoma zedoariae with potential antineoplastic and chemopreventive activities. Although the exact mechanism of action through which beta-elemene exerts its effect has yet to be fully elucidated, this agent appears to induce apoptosis through different mechanisms of action and induces cell cycle arrest at different stages based on the tumor cell type involved. Beta-elemene may sensitize cancer cells to other chemotherapeutic agents. See also: Cannabis sativa subsp. indica top (part of). Beta-elemene, also known as B-elemen or 2,4-diisopropenyl-1-methyl-1-vinylcyclohexane, is a member of the class of compounds known as elemane sesquiterpenoids. Elemane sesquiterpenoids are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. Beta-elemene is a fresh, herbal, and waxy tasting compound and can be found in a number of food items such as lovage, anise, spearmint, and orange mint, which makes beta-elemene a potential biomarker for the consumption of these food products. Beta-elemene can be found primarily in saliva. beta-Elemene belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. beta-Elemene can be found in herbs, spices, and root vegetables, which makes beta-elemene a potential biomarker for the consumption of these food products. It is a constituent of sweet flag, juniper oils, and Mentha species. β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis. β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis.

   

(-)-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].

   

2-Hexenal

InChI=1/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+

C6H10O (98.0732)


(2E)-hexenal is a 2-hexenal in which the olefinic double bond has E configuration. It occurs naturally in a wide range of fruits, vegetables, and spices. It has a role as a flavouring agent, an antibacterial agent and a plant metabolite. 2-Hexenal is a natural product found in Lonicera japonica, Origanum sipyleum, and other organisms with data available. 2-Hexenal is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. 2-Hexenal is found in allspice. 2-Hexenal is used in perfumery and flavourings. 2-Hexenal belongs to the family of Medium-chain Aldehydes. These are An aldehyde with a chain length containing between 6 and 12 carbon atoms. 2-Hexenal (CAS: 505-57-7), also known as 2-hexenaldehyde or 3-propylacrolein, belongs to the class of organic compounds known as medium-chain aldehydes. These are aldehydes with a chain length containing between 6 and 12 carbon atoms. Thus, 2-hexenal is considered to be a fatty aldehyde lipid molecule. Outside of the human body, 2-hexenal is found, on average, in the highest concentration within a few different foods, such as corn, tea, and bilberries. 2-Hexenal has also been detected, but not quantified in, several different foods, such as common wheat, ginkgo nuts, spearmints, sunflowers, and watermelons. This could make 2-hexenal a potential biomarker for the consumption of these foods. (E)-2-Hexenal is found in allspice. It is used in perfumery and flavouring. (E)-2-Hexenal has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018757 - GABA Modulators Acquisition and generation of the data is financially supported in part by CREST/JST. Trans-?2-?Hexenal can be used for the determination of low-molecular-weight carbonyl compounds which are reactive with biological nucleophiles in biological samples[1]. Trans-?2-?Hexenal can be used for the determination of low-molecular-weight carbonyl compounds which are reactive with biological nucleophiles in biological samples[1].

   

Polylimonene

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

C10H16 (136.1252)


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

   

(-)-beta-Pinene

Bicyclo(3.1.1)heptane, 6,6-dimethyl-2-methylene-, (1S,5S)-

C10H16 (136.1252)


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

   

beta-Myrcene

InChI=1/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H

C10H16 (136.1252)


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

   

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

Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, endo-(.+/-.)-

C10H18O (154.1358)


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

   

Verbinone

Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R-cis)-

C10H14O (150.1045)


Verbenone, also known as verbenone, (1r)-isomer, 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. Verbenone is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Verbenone is a camphor, celery, and menthol tasting compound and can be found in a number of food items such as spearmint, cabbage, white cabbage, and rosemary, which makes verbenone a potential biomarker for the consumption of these food products. Verbenone is a natural organic compound classified as a terpene that is found naturally in a variety of plants. The chemical has a pleasant characteristic odor. Besides being a natural constituent of plants, it and its analogs are insect pheromones. In particular, verbenone when formulated in a long-lasting matrix has an important role in the control of bark beetles such as the mountain pine beetle and the Southern pine bark beetle . 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one is a carbobicyclic compound that is bicyclo[3.1.1]heptane which is substituted by an oxo group at position 2 and by methyl groups at positions 4, 6 and 6, and which contains a double bond between positions 3 and 4. It is a carbobicyclic compound, a cyclic ketone and an enone. Verbenone is a natural product found in Eucalyptus fasciculosa, Eucalyptus intertexta, and other organisms with data available. Verbenone ((-)-Verbenone) is a natural terpene in leaves of the tree, Verbena officinalis[1]. Verbenone has anti-aggregation pheromone and interrupts the attraction of bark beetles to their aggregation pheromones[2]. Verbenone ((-)-Verbenone) is a natural terpene in leaves of the tree, Verbena officinalis[1]. Verbenone has anti-aggregation pheromone and interrupts the attraction of bark beetles to their aggregation pheromones[2].

   

alpha-Humulene

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

C15H24 (204.1878)


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

   

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].

   

gamma-Cadinene

Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4-methylene-1-(1-methylethyl)-, (1alpha,4abeta,8aalpha)-

C15H24 (204.1878)


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

   

p-Menth-1-en-4-ol

Terpinen 4-ol, primary pharmaceutical reference standard

C10H18O (154.1358)


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

   

alpha-Terpinene

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

C10H16 (136.1252)


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

   

gamma-Terpinene

1-Isopropyl-4-methyl-1,4-cyclohexadiene, p-Mentha-1,4-diene

C10H16 (136.1252)


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

   

(+)-alpha-Pinene

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

C10H16 (136.1252)


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

   

Geranial

trans-3,7-Dimethyl-2,6-octadien-1-al

C10H16O (152.1201)


Geranial, also known as 3,7-dimethyl-2,6-octadienal, citral or lemonal, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, citral is considered to be an isoprenoid lipid. Two different isomers of 3,7-dimethyl-2,6-octadienal exist. The E-isomer or trans-isomer is known as geranial or citral A. The Z-isomer or cis-isomer is known as neral or citral B. 3,7-dimethyl-2,6-octadienal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Citral is present in the oils of several plants, including lemon myrtle (90-98\\\\%), Litsea citrata (90\\\\%), Litsea cubeba, lemongrass (65-80\\\\%), lemon tea-tree (70-80\\\\%), Ocimum gratissimum, Lindera citriodora, Calypranthes parriculata, petitgrain, lemon verbena, lemon ironbark, lemon balm, lime, lemon and orange. Citral has also been reported to be found in Cannabis sativa (PMID:6991645 , 26657499 ). Citral has a strong lemon (citrus) odor. Nerals lemon odor is less intense, but sweeter. Citral is therefore an aroma compound used in perfumery for its citrus effect. Citral is also used as a flavor and for fortifying lemon oil. It has strong antimicrobial qualities (PMID:28974979 ) and pheromonal effects in nematodes and insects (PMID:26973536 ). Citral is used in the synthesis of vitamin A, lycopene, ionone, and methylionone (a compound used to mask the smell of smoke). Occurs in lemon grass oil (Cymbopogon citratus), lemon, orange and many other essential oils; flavouring ingredient. Geranial is found in many foods, some of which are watermelon, nutmeg, cloud ear fungus, and yellow wax bean. Citral is a monoterpene found in Cymbopogon citratus essential oil, with antihyperalgesic, anti-nociceptive and anti-inflammatory effects[1]. Citral is a monoterpene found in Cymbopogon citratus essential oil, with antihyperalgesic, anti-nociceptive and anti-inflammatory effects[1].

   

17a-Ethynylestradiol

(1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

C20H24O2 (296.1776)


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

   

alpha-Copaene

TRICYCLO(4.4.0.02,7)DEC-3-ENE, 1,3-DIMETHYL-8-(1-METHYLETHYL)-, (1R,2S,6S,7S,8S)-

C15H24 (204.1878)


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

   

Camphene

3,3-Dimethyl-2-methylidenebicyclo[2.2.1]heptane

C10H16 (136.1252)


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

   

(-)-trans-Carveol

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

C10H16O (152.1201)


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

   

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.

   

cis-Sabinene hydrate

(1S,2R,5R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hexan-2-ol

C10H18O (154.1358)


Cis-sabinene hydrate is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, cis-sabinene hydrate is considered to be an isoprenoid lipid molecule. Cis-sabinene hydrate is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Cis-sabinene hydrate is a balsamic tasting compound and can be found in a number of food items such as sweet marjoram, spearmint, common sage, and pot marjoram, which makes cis-sabinene hydrate a potential biomarker for the consumption of these food products.

   

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

1,2,3,5,6,8a-hexahydro-4,7-Dimethyl-1-(1-methylethyl)-(1S,8ar)-naphthalene

C15H24 (204.1878)


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

   

beta-Caryophyllene

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

C15H24 (204.1878)


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

   

alpha-Cubebene

(1R,5S,6R,7S,10R)-4,10-dimethyl-7-(propan-2-yl)tricyclo[4.4.0.0^{1,5}]dec-3-ene

C15H24 (204.1878)


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

   

(-)-Pinocarvone

6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-one

C10H14O (150.1045)


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

   

alpha-Terpineol

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

C10H18O (154.1358)


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

   

2-Pinen-10-ol

{6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl}methanol

C10H16O (152.1201)


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

   

Myrtenal

6,6-Dimethyl-bicyclo[3,1,1]hept-2-ene-2-carboxaldehyde

C10H14O (150.1045)


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

   

Pinocarveol

6,6-Dimethyl-3-hydroxy-2-methylenebicyclo(3.1.1)heptane

C10H16O (152.1201)


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

   

cis-Citral

(2Z)-3,7-Dimethyl-2,6-octadien-1-al

C10H16O (152.1201)


Neral, also known as cis-citral or citral b, is a member of the class of compounds known as acyclic monoterpenoids. Acyclic monoterpenoids are monoterpenes that do not contain a cycle. Thus, neral is considered to be an isoprenoid lipid molecule. Neral is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Neral is a sweet, citral, and lemon tasting compound and can be found in a number of food items such as oval-leaf huckleberry, lime, onion-family vegetables, and biscuit, which makes neral a potential biomarker for the consumption of these food products. Neral may refer to: An isomer of Citral Neral, India, a town in Raigad district in the Indian state of Maharashtra Neral railway station A Romulan from Star Trek . cis-Citral, also known as neural or citral B, is the Z-isomer of the terpenoid citral. Citral is found in carrot.

   

Pinene

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

C10H16 (136.1252)


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

   

Epimuurolene

1,2,3,4,4a,5,6,8a-Octahydro-7-methyl-4-methylene-1-(1-methylethyl)-(1S,4aR,8aR)-Naphthalene

C15H24 (204.1878)


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

   

β-Pinene

(1S,5S)-7,7-dimethyl-4-methylidene-bicyclo[3.1.1]heptane

C10H16 (136.1252)


An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants. Widely distributed in plants, usually associated with a-Pinene JPV84-W but in smaller amounts. Found in lime peel oil, ginger, nutmeg, mace, bitter fennel, rosemary and sage. Flavour ingredient β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity[1][2]. β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity[1][2].

   

Stirrup

InChI=1\C15H26O\c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16\h7,9,11,16H,5-6,8,10,12H2,1-4H3\b14-9+,15-11

C15H26O (222.1984)


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

   

Carveol

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

C10H16O (152.1201)


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.

   

gamma-Muurolene

(1R,4aR,8aS)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

C15H24 (204.1878)


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

   

beta-Bourbonene

Cyclobuta[1,2:3,4]dicyclopentene,decahydro-3a-methyl-6-methylene-1-(1-methylethyl)-, (1S,3aS,3bR,6aS,6bR)-

C15H24 (204.1878)


beta-Bourbonene is found in cloves. beta-Bourbonene is a flavouring agent.

   

(-)-Borneol

1,7,7-Trimethyl-(1R,2S,4R)-rel-bicyclo[2.2.1]heptan-2-ol

C10H18O (154.1358)


(-)-Borneol is found in common thyme and in turmeric. (-)-Borneol is a constituent of Blumea balsamifera (sambong). Both Borneol and Isoborneol and their acetates and formates are used as flavouring agents Constituent of Blumea balsamifera (sambong). (-)-Borneol is found in many foods, some of which are tea, coriander, common thyme, and cornmint. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2]. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2].

   

(1R,4S,5R)-4-Thujanol

(1R,2S,5R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hexan-2-ol

C10H18O (154.1358)


(1R,4S,5R)-4-Thujanol is found in herbs and spices. (1R,4S,5R)-4-Thujanol is a constituent of the essential oil of American peppermint and other Mentha species (1R,4S,5R)-4-Thujanol is a flavouring agent Constituent of the essential oil of American peppermint and other Mentha subspecies Flavouring agent. (1R,4S,5R)-4-Thujanol is found in herbs and spices.

   

delta-Amorphene

4,7-Dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthalene

C15H24 (204.1878)


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

   

cis-Ocimene

(Z)-3,7-dimethylocta-1,3,6,-triene

C10H16 (136.1252)


Ocimene refers to several isomeric hydrocarbons. The ocimenes are monoterpenes found within a variety of plants and fruits. alpha-Ocimene and the two beta-ocimenes differ in the position of the isolated double bond: it is terminal in the alpha isomer. alpha-Ocimene is 3,7-dimethyl-1,3,7-octatriene. beta-Ocimene is 3,7-dimethyl-1,3,6-octatriene. beta-Ocimene exists in two stereoisomeric forms, cis and trans, with respect to the central double bond. The ocimenes are often found naturally as mixtures of the various forms. The mixture (as well as the pure compounds) is an oil with a pleasant odor. It is used in perfumery. cis-beta-Ocimene is found in many foods, some of which are cornmint, sweet orange, sweet basil, and common sage. cis-Ocimene is found in allspice. Ocimene refers to several isomeric hydrocarbons. The ocimenes are monoterpenes found within a variety of plants and fruits. alpha-Ocimene and the two beta-ocimenes differ in the position of the isolated double bond: it is terminal in the alpha isomer. alpha-Ocimene is 3,7-dimethyl-1,3,7-octatriene. beta-Ocimene is 3,7-dimethyl-1,3,6-octatriene. beta-Ocimene exists in two stereoisomeric forms, cis and trans, with respect to the central double bond. The ocimenes are often found naturally as mixtures of the various forms. The mixture (as well as the pure compounds) is an oil with a pleasant odor. It is used in perfumery. (Wikipedia

   

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

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

C10H18O (154.1358)


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

   

(-)-3-Thujene

(1R,5S)-2-Methyl-5-(propan-2-yl)bicyclo[3.1.0]hex-2-ene

C10H16 (136.1252)


Xi-3-thujene, also known as alpha-thujen or 5-isopropyl-2-methylbicyclo[3.1.0]hex-2-ene, 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. Xi-3-thujene can be found in herbs and spices, which makes xi-3-thujene a potential biomarker for the consumption of this food product. xi-3-Thujene is found in herbs and spices. xi-3-Thujene is isolated from Indian olibanum tree (Boswellia serrata), Eucalyptus species, dill, juniper, coriander and many other plant oils. (Opt. rotn. frequently not reported).

   

alpha-Phellandrene

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

C10H16 (136.1252)


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

   

Hexenal

alpha,beta-Hexylenaldehyde

C6H10O (98.0732)


Constituent of many foods. Flavouring ingredient. 2-Hexenal is found in many foods, some of which are black elderberry, ginkgo nuts, cucumber, and burdock. Trans-?2-?Hexenal can be used for the determination of low-molecular-weight carbonyl compounds which are reactive with biological nucleophiles in biological samples[1]. Trans-?2-?Hexenal can be used for the determination of low-molecular-weight carbonyl compounds which are reactive with biological nucleophiles in biological samples[1].

   

Nerolidol

(E)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol, trans-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol

C15H26O (222.1984)


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

   

alpha-Campholenal

(+)-alpha-Campholenal

C10H16O (152.1201)


   

α-phellandrene

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

C10H16 (136.1252)


One of a pair of phellandrene cyclic monoterpene double-bond isomers in which both double bonds are endocyclic (cf. alpha-phellandrene, where one of them is exocyclic).

   

myrtenal

BICYCLO(3.1.1)HEPT-2-ENE-2-CARBOXALDEHYDE, 6,6-DIMETHYL-, (1R,5S)-REL-

C10H14O (150.1045)


(-)-Myrtenal is a natural product found in Cyperus articulatus, Forsythia viridissima, and other organisms with data available. (?)-Myrtenal ((1R)-(?)-Myrtenal) is an orally active terpene with antitumour activity. (?)-Myrtenal ameliorates hyperglycemia by enhancing GLUT2 through Akt in the skeletal muscle and liver of diabetic rats[1][2]. (?)-Myrtenal ((1R)-(?)-Myrtenal) is an orally active terpene with antitumour activity. (?)-Myrtenal ameliorates hyperglycemia by enhancing GLUT2 through Akt in the skeletal muscle and liver of diabetic rats[1][2]. (?)-Myrtenal ((1R)-(?)-Myrtenal) is an orally active terpene with antitumour activity. (?)-Myrtenal ameliorates hyperglycemia by enhancing GLUT2 through Akt in the skeletal muscle and liver of diabetic rats[1][2]. (?)-Myrtenal ((1R)-(?)-Myrtenal) is an orally active terpene with antitumour activity. (?)-Myrtenal ameliorates hyperglycemia by enhancing GLUT2 through Akt in the skeletal muscle and liver of diabetic rats[1][2]. (?)-Myrtenal ((1R)-(?)-Myrtenal) is an orally active terpene with antitumour activity. (?)-Myrtenal ameliorates hyperglycemia by enhancing GLUT2 through Akt in the skeletal muscle and liver of diabetic rats[1][2]. (?)-Myrtenal ((1R)-(?)-Myrtenal) is an orally active terpene with antitumour activity. (?)-Myrtenal ameliorates hyperglycemia by enhancing GLUT2 through Akt in the skeletal muscle and liver of diabetic rats[1][2].

   

Terpenol

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

C10H18O (154.1358)


Alpha-terpineol is a terpineol that is propan-2-ol substituted by a 4-methylcyclohex-3-en-1-yl group at position 2. It has a role as a plant metabolite. alpha-TERPINEOL is a natural product found in Nepeta nepetella, Xylopia aromatica, and other organisms with data available. 2-(4-Methyl-3-cyclohexen-1-yl)-2-propanol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Coriander Oil (part of); Cannabis sativa subsp. indica top (part of); Peumus boldus leaf (part of). A terpineol that is propan-2-ol substituted by a 4-methylcyclohex-3-en-1-yl group at position 2. (-)-α-Terpineol ((S)-α-Terpineol), a monoterpene compound, is one of compounds in Melaleuca alternifolia[1]. (-)-α-Terpineol ((S)-α-Terpineol), a monoterpene compound, is one of compounds in Melaleuca alternifolia[1]. (-)-α-Terpineol ((S)-α-Terpineol), a monoterpene compound, is one of compounds in Melaleuca alternifolia[1]. (-)-α-Terpineol ((S)-α-Terpineol), a monoterpene compound, is one of compounds in Melaleuca alternifolia[1]. α-Terpineol is isolated from Eucalyptus globulus Labill, exhibits strong antimicrobial activity against periodontopathic and cariogenic bacteria[1]. α-Terpineol possesses antifungal activity against T. mentagrophytes, and the activity might lead to irreversible cellular disruption[2]. α-Terpineol is isolated from Eucalyptus globulus Labill, exhibits strong antimicrobial activity against periodontopathic and cariogenic bacteria[1]. α-Terpineol possesses antifungal activity against T. mentagrophytes, and the activity might lead to irreversible cellular disruption[2].

   

Citral

3-01-00-03053 (Beilstein Handbook Reference)

C10H16O (152.1201)


An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85\\\\%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange. Citral is a monoterpene found in Cymbopogon citratus essential oil, with antihyperalgesic, anti-nociceptive and anti-inflammatory effects[1]. Citral is a monoterpene found in Cymbopogon citratus essential oil, with antihyperalgesic, anti-nociceptive and anti-inflammatory effects[1].

   

Ethynyl estradiol

17a-Ethynylestradiol

C20H24O2 (296.1776)


G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CA - Natural and semisynthetic estrogens, plain L - Antineoplastic and immunomodulating agents > L02 - Endocrine therapy > L02A - Hormones and related agents > L02AA - Estrogens D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. CONFIDENCE standard compound; EAWAG_UCHEM_ID 3065 EAWAG_UCHEM_ID 3065; CONFIDENCE standard compound Ethinylestradiol (Ethynyl estradiol) is a biologically active estrogen. Ethinylestradiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. Ethinylestradiol (Ethynyl estradiol) is a biologically active estrogen. Ethinylestradiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

   

Verbenone

Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R-cis)-

C10H14O (150.1045)


R - Respiratory system > R05 - Cough and cold preparations > R05C - Expectorants, excl. combinations with cough suppressants > R05CA - Expectorants 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one is a carbobicyclic compound that is bicyclo[3.1.1]heptane which is substituted by an oxo group at position 2 and by methyl groups at positions 4, 6 and 6, and which contains a double bond between positions 3 and 4. It is a carbobicyclic compound, a cyclic ketone and an enone. Verbenone is a natural product found in Eucalyptus fasciculosa, Eucalyptus intertexta, and other organisms with data available. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.872 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.873 Verbenone ((-)-Verbenone) is a natural terpene in leaves of the tree, Verbena officinalis[1]. Verbenone has anti-aggregation pheromone and interrupts the attraction of bark beetles to their aggregation pheromones[2]. Verbenone ((-)-Verbenone) is a natural terpene in leaves of the tree, Verbena officinalis[1]. Verbenone has anti-aggregation pheromone and interrupts the attraction of bark beetles to their aggregation pheromones[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].

   

Carveol

2-Methyl-5-[1-methylethenyl]-2-cyclohexen-1-ol

C10H16O (152.1201)


Carveol is an endogenous metabolite. Carveol is an endogenous metabolite.

   

caryophyllene

(-)-beta-Caryophyllene

C15H24 (204.1878)


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

   

beta-Bourbonene

Cyclobuta[1,2:3,4]dicyclopentene,decahydro-3a-methyl-6-methylene-1-(1-methylethyl)-, (1S,3aS,3bR,6aS,6bR)-

C15H24 (204.1878)


Flavouring agent. beta-Bourbonene is found in many foods, some of which are rosemary, common oregano, sweet basil, and winter savory.

   

D-Amorphene

4,7-Dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthalene

C15H24 (204.1878)


   

borneol

1,7,7-Trimethyl-(1R,2S,4R)-rel-bicyclo[2.2.1]heptan-2-ol

C10H18O (154.1358)


Flavouring agent. (±)-Borneol is found in many foods, some of which are pot marjoram, pepper (spice), saffron, and german camomile. Constituent of Curcuma aromatica and other plants. (+)-Borneol is found in nutmeg, herbs and spices, and ginger. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2]. Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties. Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)[1][2].

   

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].

   

g-Muurolene

7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

C15H24 (204.1878)


   

g-Cadinene

1,2,3,4,4a,5,6,8a-Octahydro-7-methyl-4-methylene-1-(1-methylethyl)-(1S,4aR,8aR)-Naphthalene

C15H24 (204.1878)


   

Neral

InChI=1\C10H16O\c1-9(2)5-4-6-10(3)7-8-11\h5,7-8H,4,6H2,1-3H3\b10-7

C10H16O (152.1201)


An enal that is 3,7-dimethyloctanal with unsaturation at positions C-2 and C-6. It has been isolated form the essential oils of plant species like lemon.

   

(E)-carveol

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

C10H16O (152.1201)


   

P-CYMENE

P-CYMENE

C10H14 (134.1095)


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

   

Pinocarvone

Pinocarvone

C10H14O (150.1045)


A bridged compound resulting from rearrangement of carvone.

   

Terpinolen

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

C10H16 (136.1252)


   

nerolidol

(±)-trans-Nerolidol

C15H26O (222.1984)


A farnesane sesquiterpenoid that is dodeca-1,6,10-triene which carries methyl groups at positions 3, 7 and 11 and a hydroxy group at position 3. It is a natural product that is present in various flowers and plants with a floral odor. Chemically, it exists in two geometric isomers, trans and cis forms. It is widely used in cosmetics (e.g. shampoos and perfumes), in non-cosmetic products (e.g. detergents and cleansers) and also as a food flavoring agent. Nerolidol is a natural membrane-active sesquiterpene, with antitumor, antibacterial, antifungal and antiparasitic activity[1]. Nerolidol is a natural membrane-active sesquiterpene, with antitumor, antibacterial, antifungal and antiparasitic activity[1]. trans-Nerolidol is a sesquiterpene alcohol. It can be isolated from f aerial parts of Warionia saharae ex Benth. trans-Nerolidol improves the anti-proliferative effect of Doxorubicin (HY-15142A) against intestinal cancer cells in vitro. trans-Nerolidol also has anti-fungal activity[1][2]. trans-Nerolidol is a sesquiterpene alcohol. It can be isolated from f aerial parts of Warionia saharae ex Benth. trans-Nerolidol improves the anti-proliferative effect of Doxorubicin (HY-15142A) against intestinal cancer cells in vitro. trans-Nerolidol also has anti-fungal activity[1][2].

   

(+)-DELTA-CADINENE

(+)-DELTA-CADINENE

C15H24 (204.1878)


A member of the cadinene family of sesquiterpenes in which the double bonds are located at the 4-4a and 7-8 positions, and in which the isopropyl group at position 1 is cis to the hydrogen at the adjacent bridgehead carbon (the 1S,8aR-enantiomer).

   

alpha-Cubebene

(-)-Alpha-Cubebene

C15H24 (204.1878)


A tricyclic sesquiterpene with formula C15H24, isolated from Hungarian thyme, citrus fruit, chamomile, and several other flowering plants. Constituent of oil of cubeb pepper (Piper cubeba). alpha-Cubebene is found in many foods, some of which are parsley, ginger, nutmeg, and lemon balm.

   

alpha-terpineol

alpha-terpineol

C10H18O (154.1358)


α-Terpineol is isolated from Eucalyptus globulus Labill, exhibits strong antimicrobial activity against periodontopathic and cariogenic bacteria[1]. α-Terpineol possesses antifungal activity against T. mentagrophytes, and the activity might lead to irreversible cellular disruption[2]. α-Terpineol is isolated from Eucalyptus globulus Labill, exhibits strong antimicrobial activity against periodontopathic and cariogenic bacteria[1]. α-Terpineol possesses antifungal activity against T. mentagrophytes, and the activity might lead to irreversible cellular disruption[2].

   

Humulene

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

C15H24 (204.1878)


α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1]. α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1].

   

Cymol

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

C10H14 (134.1095)


   

α-Pinene

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

C10H16 (136.1252)


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

   

Myrcene

InChI=1\C10H16\c1-5-10(4)8-6-7-9(2)3\h5,7H,1,4,6,8H2,2-3H

C10H16 (136.1252)


Myrcene (β-Myrcene), an aromatic volatile compound, suppresses TNFα-induced NF-κB activity. Myrcene has anti-invasive effect[1][2]. Myrcene (β-Myrcene), an aromatic volatile compound, suppresses TNFα-induced NF-κB activity. Myrcene has anti-invasive effect[1][2].

   

Moslene

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

C10H16 (136.1252)


γ-Terpinene, a monoterpene, is an orally active antioxidant compound which can scavenge radicals directly. γ-Terpinene has potent antinociception activity[1]. γ-Terpinene, a monoterpene, is an orally active antioxidant compound which can scavenge radicals directly. γ-Terpinene has potent antinociception activity[1].

   

Tereben

Dipentene Fluka specially purified fraction of terpene hydrocarbons

C10H16 (136.1252)


   

CHEBI:15389

2-Cyclohexen-1-ol, 2-methyl-5-(1-methylethenyl)-, (1S,5R)-

C10H16O (152.1201)


   

CHEBI:15385

(1S,8AR)-4,7-dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthalene

C15H24 (204.1878)


   

(±)-β-Elemene

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

C15H24 (204.1878)


β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis. β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis.

   

Terpilene

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

C10H16 (136.1252)


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].

   

Hexenal

4-01-00-03468 (Beilstein Handbook Reference)

C6H10O (98.0732)


Trans-?2-?Hexenal can be used for the determination of low-molecular-weight carbonyl compounds which are reactive with biological nucleophiles in biological samples[1]. Trans-?2-?Hexenal can be used for the determination of low-molecular-weight carbonyl compounds which are reactive with biological nucleophiles in biological samples[1].

   

beta-Bourbonene

Cyclobuta[1,2:3,4]dicyclopentene,decahydro-3a-methyl-6-methylene-1-(1-methylethyl)-, (1S,3aS,3bR,6aS,6bR)-

C15H24 (204.1878)


Bourbonene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, bourbonene is considered to be an isoprenoid lipid molecule. Bourbonene can be found in orange mint, which makes bourbonene a potential biomarker for the consumption of this food product. beta-Bourbonene is found in cloves. beta-Bourbonene is a flavouring agent.

   

α-Copaene

alpha-copaene

C15H24 (204.1878)


   

Borneol

Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, endo-(.+/-.)-

C10H18O (154.1358)


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

   

(+)-Camphene

(+)-Camphene

C10H16 (136.1252)


A monoterpene with a bicyclic skeleton that is bicyclo[2.2.1]heptane substituted by geminal methyl groups at position 2 and a methylidene group at position 3. It is a widespread natural product found in many essential oils.

   

TERPINOLENE

TERPINOLENE

C10H16 (136.1252)


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

   

(+)-gamma-cadinene

(+)-gamma-cadinene

C15H24 (204.1878)


A member of the cadinene family of sesquiterpenes in which the isopropyl group is cis to the hydrogen at the adjacent bridgehead carbon (the 1S,4aR,8aR enantiomer).

   

beta-Ocimene, (3Z)-

(Z)-3,7-dimethylocta-1,3,6,-triene

C10H16 (136.1252)


   

Bicyclo[3.1.0]hex-2-ene, 2-methyl-5-(1-methylethyl)-

Bicyclo[3.1.0]hex-2-ene, 2-methyl-5-(1-methylethyl)-

C10H16 (136.1252)


   

Pinocarveol

Bicyclo[3.1.1]heptan-3-ol,6,6-dimethyl-2-methylene-

C10H16O (152.1201)


A pinane monoterpenoid that is a bicyclo[3.1.1]heptane substituted by two methyl groups at position 6, a methylidene group at position 2 and a hydroxy group at position 3.

   

nerolidol isomers

nerolidol isomers

C15H26O (222.1984)


   

(s)-trans-verbenol

(s)-trans-verbenol

C10H16O (152.1201)


   
   

(4e)-5,9-dimethyldeca-4,8-dienoic acid

(4e)-5,9-dimethyldeca-4,8-dienoic acid

C12H20O2 (196.1463)


   

(r)-cis-verbenol

(r)-cis-verbenol

C10H16O (152.1201)