1.0 2011-05-05 17:57:39 UTC 2025-11-19 02:39:57 UTC FDB021833 (±)-Neoisomenthol (+)-neoisomenthol, also known as cis-1,3,cis-1,4-menthol or iso-neomenthol, 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. Thus, (+)-neoisomenthol is considered to be an isoprenoid lipid molecule (+)-neoisomenthol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Within the cell, (+)-neoisomenthol is primarily located in the membrane (predicted from logP). (±)-Neoisomenthol all-cis-2-Isopropyl-5-methylcyclohexanol cis-1,3,cis-1,4-menthol Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1a,2a,5a)- DL-Neoisomenthol Isoneomenthol rel-(1R,2R,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol C10H20O 156.2652 156.151415262 (1S,2S,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol (1S,2S,5S)-2-isopropyl-5-methylcyclohexan-1-ol 491-02-1 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-GUBZILKMSA-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 logp 2.68 ALOGPS logs -2.45 ALOGPS solubility 5.58e-01 g/l ALOGPS melting_point Mp 14° logp 2.66 ChemAxon pka_strongest_acidic 19.55 ChemAxon pka_strongest_basic -0.81 ChemAxon iupac (1S,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-GUBZILKMSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 47.45 ChemAxon polarizability 19.48 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 16720 Specdb::CMs 44547 Specdb::CMs 148379 Specdb::MsMs 62823 Specdb::MsMs 62824 Specdb::MsMs 62825 Specdb::MsMs 119628 Specdb::MsMs 119629 Specdb::MsMs 119630 Specdb::MsMs 2814104 Specdb::MsMs 2814105 Specdb::MsMs 2814106 Specdb::MsMs 2892099 Specdb::MsMs 2892100 Specdb::MsMs 2892101 Specdb::MsIr 6992 Specdb::MsIr 6993 Specdb::MsIr 6994 HMDB0035764 18451 Cornmint Type 1 specific Mentha arvensis 292239 menthol