1.02010-04-08 22:10:54 UTC2020-09-17 15:32:30 UTCFDB013765(+)-alpha-Pinenealpha-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-ene1R-(+)-a-pinene1R-(+)-alpha-pinene1R-a-Pinene1R-alpha-Pinene2-Pinene2,6,6-Trimethylbicyclo[3.1.1]hept-2-enea-PineneAlpha-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-pinenePin-2(3)-eneα-pineneC10H16136.234136.125200512(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene(+)-α-pinene7785-70-8CC1=CC[C@@H]2C[C@H]1C2(C)CInChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1GRWFGVWFFZKLTI-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 monoterpenoidsOrganic compoundsLipids and lipid-like moleculesPrenol lipidsMonoterpenoidsAliphatic homopolycyclic compoundsBranched unsaturated hydrocarbonsCyclic olefinsPolycyclic hydrocarbonsUnsaturated aliphatic hydrocarbonsAliphatic homopolycyclic compoundBicyclic monoterpenoidBranched unsaturated hydrocarbonCyclic olefinHydrocarbonOlefinPinane monoterpenoidPolycyclic hydrocarbonUnsaturated aliphatic hydrocarbonUnsaturated hydrocarbonBicyclic monoterpenoidsBicyclic monoterpenoidsCyclic monoterpenesalpha-pineneLiquidlogp3.66logs-2.94solubility1.58e-01 g/lmelting_pointMp ?50°logp2.8iupac(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-eneaverage_mass136.234mono_mass136.125200512smilesCC1=CC[C@@H]2C[C@H]1C2(C)CformulaC10H16inchiInChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1inchikeyGRWFGVWFFZKLTI-RKDXNWHRSA-Npolar_surface_area0refractivity44.72polarizability17.22rotatable_bond_count0acceptor_count0donor_count0physiological_charge0formal_charge0Specdb::CMs18251Specdb::CMs27997Specdb::CMs101742Specdb::CMs171811Specdb::MsMs49719Specdb::MsMs49720Specdb::MsMs49721Specdb::MsMs121791Specdb::MsMs121792Specdb::MsMs121793Specdb::MsMs2283559Specdb::MsMs2283560Specdb::MsMs2283561Specdb::MsMs3086014Specdb::MsMs3086015Specdb::MsMs3086016HMDB0652528261AlmondType 1specificPrunus dulcis3755AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462CarrotType 1specificDaucus carota ssp. sativus79200Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984FennelType 1specificFoeniculum vulgare48038GingerType 1specificZingiber officinale94328Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Milk (Cow)Type 2specific0.000630.0009830.000378uMMountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PeppermintType 1specificMentha X piperita342567.957.957.95mg/100 gPheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823harshmintyterpene