1.0 2010-04-08 22:11:20 UTC 2025-11-19 00:47:39 UTC FDB014552 (R)-alpha-Terpineol Œ±-Terpineol, also known as terpineol or p-menth-1-en-8-ol, 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 an isopropyl group at positions 1 and 4 of ring, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 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 the plastids. 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. There are three known terpineol isomers including Œ±, Œ≤, and Œ≥-terpineol, with the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with Œ±-terpineol as the major constituent. Alpha-Terpineol is a very hydrophobic molecule, practically insoluble in water, but soluble in organic solvents such as methanol, ethanol and ethylacetate. Terpineol has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. (+)-alpha-Terpineol (+)-p-Menth-1-en-8-ol (1R)-alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanol (4R)-p-Menth-1-en-8-ol (6R)-p-Menth-1-en-8-ol (R)-(+)-alpha-Terpineol (R)-(+)-p-Menth-1-en-8-ol (R)-2-(4-Methyl-3-cyclohexenyl)isopropanol (R)-alpha,alpha,4-Trimethylcyclohex-3-ene-1-methanol (R)-p-Menth-1-en-8-ol 2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol D-alpha-Terpineol C10H18O 154.2493 154.135765198 2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol (+)-α-terpineol 7785-53-7 CC1=CC[C@@H](CC1)C(C)(C)O InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m0/s1 WUOACPNHFRMFPN-VIFPVBQESA-N 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. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Hydrocarbon derivatives Monocyclic monoterpenoids Tertiary alcohols Alcohol Aliphatic homomonocyclic compound Hydrocarbon derivative Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Tertiary alcohol Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids alpha-terpineol logp 3.17 ALOGPS logs -2.00 ALOGPS solubility 1.56e+00 g/l ALOGPS melting_point Mp 37° logp 2.17 ChemAxon pka_strongest_acidic 19.4 ChemAxon pka_strongest_basic -0.87 ChemAxon iupac 2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol ChemAxon average_mass 154.2493 ChemAxon mono_mass 154.135765198 ChemAxon smiles CC1=CC[C@@H](CC1)C(C)(C)O ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m0/s1 ChemAxon inchikey WUOACPNHFRMFPN-VIFPVBQESA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 48.46 ChemAxon polarizability 19.07 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1923 Specdb::CMs 13638 Specdb::CMs 38692 Specdb::CMs 103767 Specdb::CMs 156516 Specdb::NmrOneD 1988 Specdb::NmrOneD 4664 Specdb::MsIr 2091 Specdb::MsIr 2092 Specdb::MsIr 2093 Specdb::MsMs 2355 Specdb::MsMs 2356 Specdb::MsMs 2357 Specdb::MsMs 296065 Specdb::MsMs 296066 Specdb::MsMs 296067 Specdb::MsMs 337270 Specdb::MsMs 337271 Specdb::MsMs 337272 Specdb::MsMs 2784694 Specdb::MsMs 2784695 Specdb::MsMs 2784696 Specdb::MsMs 2921563 Specdb::MsMs 2921564 Specdb::MsMs 2921565 HMDB0004043 300 Cardamom Type 1 specific Elettaria cardamomum 105181 Cinnamon Type 1 specific Cinnamomum 13428 Lovage Type 1 specific Levisticum officinale 48042 Mentha Type 1 specific Mentha 21819 Sweet marjoram Type 1 specific Origanum majorana 268884 48.5 48.5 48.5 mg/100 g floral lilac