1.0 2010-04-08 22:10:48 UTC 2025-11-18 23:51:44 UTC FDB013581 (+)-cis-Isopulegone (-)-trans-isopulegone, also known as isopulegone or 1-methyl-4-isopropenyl-3-cyclohexanone, 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 (-)-trans-isopulegone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (-)-trans-isopulegone can be found in fats and oils, which makes (-)-trans-isopulegone a potential biomarker for the consumption of this food product. (+)-cis-Isopulegone (+)-cis-p-Menth-8-en-3-one (1R,4R)-p-Menth-8-en-3-one Andromedol Deacylasebotoxin I Grayanotoxane-3,5,6,10,14,16-hexol Grayanotoxin III Isoisopulegone C10H16O 152.2334 152.120115134 5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one isopulegone 3391-89-7 CC1CCC(C(C)=C)C(=O)C1 InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-9H,1,4-6H2,2-3H3 RMIANEGNSBUGDJ-UHFFFAOYSA-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 ketones Hydrocarbon derivatives Monocyclic monoterpenoids Organic oxides Aliphatic homomonocyclic compound Carbonyl group Cyclic ketone Hydrocarbon derivative Ketone Monocyclic monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound P-menthane monoterpenoid a monoterpenoid p-menthane monoterpenoid logp 2.42 ALOGPS logs -2.45 ALOGPS solubility 5.44e-01 g/l ALOGPS logp 2.7 ChemAxon pka_strongest_acidic 17.88 ChemAxon pka_strongest_basic -7.5 ChemAxon iupac 5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one ChemAxon average_mass 152.2334 ChemAxon mono_mass 152.120115134 ChemAxon smiles CC1CCC(C(C)=C)C(=O)C1 ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-9H,1,4-6H2,2-3H3 ChemAxon inchikey RMIANEGNSBUGDJ-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 46.3 ChemAxon polarizability 18.26 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 11351 Specdb::CMs 173883 Specdb::MsMs 9140 Specdb::MsMs 9141 Specdb::MsMs 9142 Specdb::MsMs 15812 Specdb::MsMs 15813 Specdb::MsMs 15814 Specdb::MsMs 2470848 Specdb::MsMs 2470849 Specdb::MsMs 2470850 Specdb::MsMs 2495024 Specdb::MsMs 2495025 Specdb::MsMs 2495026 HMDB0035741 Cornmint Type 1 specific Mentha arvensis 292239