1.0 2010-04-08 22:11:14 UTC 2025-11-19 00:45:54 UTC FDB014367 (+)-trans-Pinocarveol Trans-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-Pinocarveol 2(10)-Pinen-3-ol; (+)-trans-form D-trans-Pinocarveol trans-(+)-Pinocarveol C10H16O 152.2334 152.120115134 (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-ol 19894-98-5 CC1(C)[C@@H]2C[C@H]1C(=C)[C@@H](O)C2 InChI=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/s1 LCYXQUJDODZYIJ-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 monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Cyclic alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Pinane monoterpenoid Secondary alcohol logp 2.24 ALOGPS logs -1.94 ALOGPS solubility 1.76e+00 g/l ALOGPS logp 1.63 ChemAxon pka_strongest_acidic 17.94 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac (1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol ChemAxon average_mass 152.2334 ChemAxon mono_mass 152.120115134 ChemAxon smiles CC1(C)[C@@H]2C[C@H]1C(=C)[C@@H](O)C2 ChemAxon formula C10H16O ChemAxon inchi InChI=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/s1 ChemAxon inchikey LCYXQUJDODZYIJ-VGMNWLOBSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.17 ChemAxon polarizability 17.88 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 133738 Specdb::NmrOneD 133739 Specdb::NmrOneD 133740 Specdb::NmrOneD 133741 Specdb::NmrOneD 133742 Specdb::NmrOneD 133743 Specdb::NmrOneD 133744 Specdb::NmrOneD 133745 Specdb::NmrOneD 133746 Specdb::NmrOneD 133747 Specdb::NmrOneD 133748 Specdb::NmrOneD 133749 Specdb::NmrOneD 133750 Specdb::NmrOneD 133751 Specdb::NmrOneD 133752 Specdb::NmrOneD 133753 Specdb::NmrOneD 133754 Specdb::NmrOneD 133755 Specdb::NmrOneD 133756 Specdb::NmrOneD 133757 Specdb::MsIr 7110 Specdb::MsIr 7111 Specdb::MsMs 84915 Specdb::MsMs 84916 Specdb::MsMs 84917 Specdb::MsMs 146889 Specdb::MsMs 146890 Specdb::MsMs 146891 Specdb::MsMs 2693684 Specdb::MsMs 2693685 Specdb::MsMs 2693686 Specdb::MsMs 2984945 Specdb::MsMs 2984946 Specdb::MsMs 2984947 Specdb::CMs 14405 Specdb::CMs 44739 Specdb::CMs 151564 HMDB0036128 Common sage Type 1 specific Salvia officinalis 38868 Cumin Type 1 specific Cuminum cyminum 52462 3.0 3.0 3.0 mg/100 g Hyssop Type 1 specific Hyssopus officinalis 39324 11.0 11.0 11.0 mg/100 g Pepper (Spice) Type 1 specific Piper nigrum 13216 Rosemary Type 1 specific Rosmarinus officinalis 39367 3.7 3.7 3.7 mg/100 g Sweet bay Type 1 specific Laurus nobilis 85223 Anti plasmodial 532 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-malarial 416 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.