1.0 2010-04-08 22:10:54 UTC 2020-09-17 15:32:30 UTC FDB013765 (+)-alpha-Pinene alpha-Pinene, also known as 2-pinene or acintene A, belongs to the class of organic compounds known as bicyclic monoterpenoids. These 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. alpha-Pinene is considered to be an isoprenoid lipid molecule. There are two isomers of alpha-pinene: (−)-alpha-pinene and (+)-alpha-pinene. The (−)-alpha-pinene isomer is more common in European pines, whereas the (+)-alpha-isomer is more common in North America. alpha-Pinene is a neutral, hydrophobic molecule, practically insoluble in water. It exists as a clear, colorless oil. alpha-Pinene has a woody, camphoreous, piney or turpentine-like odor and a spicy, woody or herbal taste. It is widely used as a flavor and a fragrance additive and has one of the lowest boiling points of all monoterpenes. Industrially, alpha-pinene is largely used as starting material for the synthesis of terpineol, camphor, borneol and terpene resin, synthetic perfumes and resins, medicines and other synthetic organic chemicals. alpha-Pinene is found naturally in the essential oils and resins of many coniferous tree species, notably the pine (where it gets its name) as well as in non-coniferous plants such as camphorweed (Heterotheca) and big sagebrush (Artemisia tridentata). It is also found in the essential oil of rosemary, eucalyptus oil and orange peel oil. Monoterpenes, of which alpha-pinene is one of the principal species, are emitted in substantial amounts by vegetation. In the atmosphere alpha-pinene undergoes reactions with ozone, hydroxyl radicals and NO3 radicals to produce several compounds including: pinonaldehyde, norpinonaldehyde, pinic acid, pinonic acid and pinalic acid (PMID: 20017184). alpha-Pinene exhibits a wide range of physiological or drug like effects. There are well-substantiated claims that has anticoagulant, antitumor, antimicrobial, antimalarial, antioxidant, anti-inflammatory, anti-Leishmania, analgesic, gastroprotective, anxiolytic, cytoprotective, anticonvulsant, and neuroprotective effects (PMID: 31739596). alpha-Pinene exhibits activity as an acetylcholinesterase inhibitor, which may aid in memory retention. alpha-Pinene is a positive modulator of GABAA receptors and binds to the benzodiazepine binding site of the GABAA receptor (PMID: 31739596). (+)-alpha-Pinene also binds to Cytochrome P450 2B6 and is a potent inhibitor of this enzyme (PMID: 23786449). (+-)-2-Pinene (+-)-a-Pinene (+-)-alpha-Pinene (+-)-α-pinene (+)-alpha-pinene (+)-Pin-2(3)-ene (1R,5R)-2-Pinene (1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene (1R,5R)-pin-2-ene (1R)-(+)-alpha-Pinene (1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene 1R-(+)-a-pinene 1R-(+)-alpha-pinene 1R-a-Pinene 1R-alpha-Pinene 2-Pinene 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene a-Pinene Alpha-pinene(dextro) Bicyclo(3.1.1)hept-2-ene, 2,6,6-trimethyl-, (1R,5R)- Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (1R)- Dextro-alpha-pinene Pin-2(3)-ene α-pinene C10H16 136.234 136.125200512 (1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene (+)-α-pinene 7785-70-8 CC1=CC[C@@H]2C[C@H]1C2(C)C InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1 GRWFGVWFFZKLTI-RKDXNWHRSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Pinane monoterpenoid Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Bicyclic monoterpenoids Bicyclic monoterpenoids Cyclic monoterpenes alpha-pinene Liquid logp 3.66 ALOGPS logs -2.94 ALOGPS solubility 1.58e-01 g/l ALOGPS melting_point Mp ?50° logp 2.8 ChemAxon iupac (1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene ChemAxon average_mass 136.234 ChemAxon mono_mass 136.125200512 ChemAxon smiles CC1=CC[C@@H]2C[C@H]1C2(C)C ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1 ChemAxon inchikey GRWFGVWFFZKLTI-RKDXNWHRSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 44.72 ChemAxon polarizability 17.22 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 18251 Specdb::CMs 27997 Specdb::CMs 101742 Specdb::CMs 171811 Specdb::MsMs 49719 Specdb::MsMs 49720 Specdb::MsMs 49721 Specdb::MsMs 121791 Specdb::MsMs 121792 Specdb::MsMs 121793 Specdb::MsMs 2283559 Specdb::MsMs 2283560 Specdb::MsMs 2283561 Specdb::MsMs 3086014 Specdb::MsMs 3086015 Specdb::MsMs 3086016 HMDB06525 28261 Almond Type 1 specific Prunus dulcis 3755 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Carrot Type 1 specific Daucus carota ssp. sativus 79200 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Fennel Type 1 specific Foeniculum vulgare 48038 Ginger Type 1 specific Zingiber officinale 94328 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific 0.00063 0.000983 0.000378 uM Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Peppermint Type 1 specific Mentha X piperita 34256 7.95 7.95 7.95 mg/100 g Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 harsh minty terpene