1.02010-04-08 22:11:14 UTC2020-09-17 15:36:09 UTCFDB014367(+)-trans-PinocarveolTrans-Pinocarveol or simply pinocarveol 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-eritritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Trans-Pinocarveol is the (1S,3R,5S)-stereoisomer of pinocarveol. It exists as a pale, clear, yellow oil that is weakly soluble in water (1 g/L). Trans-Pinocarveol is an extremely weak basic (essentially neutral) compound, based on its pKa. It has a herbal, pine, minty or balsamic odor and a comphoreous, pine or fir needle taste. Trans-Pincarveol is found in the essential oils of hop, myssop, grapefruit, rosemary, spearmint and wormwood. It has a role as a GABA(A) modulator (PMID: 24273211), a plant metabolite, a food additive, a cosmetic/fragrance agent and a volatile oil component. With regard to its positive GABA modulating effects, Pinocarveol (along with isopulegol, verbenol, and myrtenol) are particularly potent modifiers of GABA(A) receptor function and this interaction may lead to certain sedative effects found in plants or plant oils that contain this compound (PMID: 24273211).(+)-Pinocarveol(+)-trans-Pinocarveol(1R)-(+)-trans-Pinocarveol(1R)-trans-Pinocarveol2(10)-Pinen-3-ol; (+)-trans-formD-trans-Pinocarveoltrans-(+)-PinocarveolC10H16O152.2334152.120115134(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol19894-98-5CC1(C)[C@@H]2C[C@H]1C(=C)[C@@H](O)C2InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3/t7-,8+,9+/m1/s1LCYXQUJDODZYIJ-VGMNWLOBSA-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 compoundsCyclic alcohols and derivativesHydrocarbon derivativesSecondary alcoholsAlcoholAliphatic homopolycyclic compoundBicyclic monoterpenoidCyclic alcoholHydrocarbon derivativeOrganic oxygen compoundOrganooxygen compoundPinane monoterpenoidSecondary alcohollogp2.24logs-1.94solubility1.76e+00 g/llogp1.63pka_strongest_acidic17.94pka_strongest_basic-1.5iupac(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-olaverage_mass152.2334mono_mass152.120115134smilesCC1(C)[C@@H]2C[C@H]1C(=C)[C@@H](O)C2formulaC10H16OinchiInChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3/t7-,8+,9+/m1/s1inchikeyLCYXQUJDODZYIJ-VGMNWLOBSA-Npolar_surface_area20.23refractivity45.17polarizability17.88rotatable_bond_count0acceptor_count1donor_count1physiological_charge0formal_charge0Specdb::MsIr7110Specdb::MsIr7111Specdb::CMs14405Specdb::CMs44739Specdb::CMs151564Specdb::NmrOneD133738Specdb::NmrOneD133739Specdb::NmrOneD133740Specdb::NmrOneD133741Specdb::NmrOneD133742Specdb::NmrOneD133743Specdb::NmrOneD133744Specdb::NmrOneD133745Specdb::NmrOneD133746Specdb::NmrOneD133747Specdb::NmrOneD133748Specdb::NmrOneD133749Specdb::NmrOneD133750Specdb::NmrOneD133751Specdb::NmrOneD133752Specdb::NmrOneD133753Specdb::NmrOneD133754Specdb::NmrOneD133755Specdb::NmrOneD133756Specdb::NmrOneD133757Specdb::MsMs84915Specdb::MsMs84916Specdb::MsMs84917Specdb::MsMs146889Specdb::MsMs146890Specdb::MsMs146891Specdb::MsMs2693684Specdb::MsMs2693685Specdb::MsMs2693686Specdb::MsMs2984945Specdb::MsMs2984946Specdb::MsMs2984947Common sageType 1specificSalvia officinalis38868CuminType 1specificCuminum cyminum524623.03.03.0mg/100 gHyssopType 1specificHyssopus officinalis3932411.011.011.0mg/100 gPepper (Spice)Type 1specificPiper nigrum13216RosemaryType 1specificRosmarinus officinalis393673.73.73.7mg/100 gSweet bayType 1specificLaurus nobilis85223anti malarial416A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.anti plasmodial532A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.