1.0 2011-05-05 19:53:33 UTC 2025-11-19 02:39:58 UTC FDB021835 (±)-Isomenthol (±)-isomenthol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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 (±)-isomenthol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (±)-isomenthol can be found in a number of food items such as cabbage, peppermint, sunflower, and white cabbage, which makes (±)-isomenthol a potential biomarker for the consumption of these food products. (±)-Isomenthol Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5S)-rel- DL-Isomenthol Isomenthol trans-1,3,cis-1,4-(±)-Menthol C10H20O 156.2652 156.151415262 (1R,2S,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol (1S,2R,5S)-menthol 3623-52-7 CC(C)[C@@H]1CC[C@H](C)C[C@H]1O InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9-,10+/m0/s1 NOOLISFMXDJSKH-LPEHRKFASA-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 Cyclic alcohols and derivatives Cyclohexanols Hydrocarbon derivatives Monocyclic monoterpenoids Alcohol Aliphatic homomonocyclic compound Cyclic alcohol Cyclohexanol Hydrocarbon derivative Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Secondary alcohol solid logp 2.68 ALOGPS logs -2.45 ALOGPS solubility 5.58e-01 g/l ALOGPS melting_point Mp 53-54° logp 2.66 ChemAxon pka_strongest_acidic 19.55 ChemAxon pka_strongest_basic -0.81 ChemAxon iupac (1R,2S,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol ChemAxon average_mass 156.2652 ChemAxon mono_mass 156.151415262 ChemAxon smiles CC(C)[C@@H]1CC[C@H](C)C[C@H]1O ChemAxon formula C10H20O ChemAxon inchi InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9-,10+/m0/s1 ChemAxon inchikey NOOLISFMXDJSKH-LPEHRKFASA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 47.45 ChemAxon polarizability 19.42 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 1218760 Specdb::MsMs 1218761 Specdb::MsMs 1218762 Specdb::MsMs 1334473 Specdb::MsMs 1334474 Specdb::MsMs 1334475 Specdb::MsMs 3606934 Specdb::MsMs 3606935 Specdb::MsMs 3606936 Specdb::MsMs 3606937 Specdb::MsMs 3606938 Specdb::MsMs 3606939 Cabbage Type 1 specific Brassica oleracea var. capitata 3716 Cornmint Type 1 specific Mentha arvensis 292239 Peppermint Type 1 specific Mentha X piperita 34256 16.45 16.45 16.45 mg/100 g Spearmint Type 1 specific Mentha spicata 29719 9.5 9.5 9.5 mg/100 g Sunflower Type 1 specific Helianthus annuus 4232 White cabbage Type 1 specific Brassica oleracea L. var. capitata L. f. alba DC. Anti acetylcholinesterase 76 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.