1.0 2010-04-08 22:10:52 UTC 2020-09-17 15:30:23 UTC FDB013718 (R)-Carvone Carvone, with R and S isomers, also known as carvol or limonen-6-one, 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. Carvone is a neutral compound. Carvone is a naturally occurring organic compound found in many essential oils but is most abundant in the oils from caraway seeds (Carum carvi), spearmint (Mentha spicata), and dill (PMID: 27427817). Carvone is occasionally found as a component of biological fluids in normal individuals. Both carvones (R, S) are used in the food and flavor industry (http//doi:10.1016/j.foodchem.2005.01.003). R-carvone is also used in air freshening products and in essential oils used in aromatherapy and alternative medicine. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841 (PMID: 5556886, 2477620). Carvone may help in the management of diseases (PMID: 30374904) and had been considered as an adjuvant for treatment of cancer patients (PMID: 30087792) and patients with epilepsy (PMID: 31239862). It also has been successfully used as a biopesticide (PMID: 30250476). (-)-(4R)-Carvone (-)-(r)-carvone (-)-carvone (-)-p-Mentha-6,8-dien-2-one (4R)-(-)-Carvone (4R)-Carvone (5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one (R)-(-)-Carvone (R)-(-)-P-Mentha-6,8-dien-2-one (R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one (R)-5-Isopropenyl-2-methylcyclohex-2-en-1-one (r)-carvone 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)- 2-Methyl-5-(1-methylethenyl)-(R)-2-cyclohexen-1-one L-1-Methyl-4-isopropenyl-6-cyclohexen-2-one L-Carvone L-P-Mentha-1(6),8-dien-2-one L(-)-carvone Levo-carvone p-Mentha-6,8-dien-2-one, (R)-(-)- C10H14O 150.2176 150.10446507 (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (-)-carvone 6485-40-1 CC(=C)[C@@H]1CC=C(C)C(=O)C1 InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1 ULDHMXUKGWMISQ-SECBINFHSA-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 Cyclohexenones Hydrocarbon derivatives Monocyclic monoterpenoids Organic oxides Aliphatic homomonocyclic compound Carbonyl group Cyclic ketone Cyclohexenone Hydrocarbon derivative Ketone Monocyclic monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids carvone Liquid logp 2.77 ALOGPS logs -2.11 ALOGPS solubility 1.16e+00 g/l ALOGPS melting_point <15 oC logp 2.55 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one ChemAxon average_mass 150.2176 ChemAxon mono_mass 150.10446507 ChemAxon smiles CC(=C)[C@@H]1CC=C(C)C(=O)C1 ChemAxon formula C10H14O ChemAxon inchi InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1 ChemAxon inchikey ULDHMXUKGWMISQ-SECBINFHSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 47.17 ChemAxon polarizability 17.65 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 1761 Specdb::NmrOneD 3954 Specdb::NmrOneD 4236 Specdb::CMs 18599 Specdb::CMs 28042 Specdb::CMs 101698 Specdb::CMs 102465 Specdb::CMs 102466 Specdb::CMs 132648 Specdb::CMs 140382 Specdb::MsMs 60771 Specdb::MsMs 60772 Specdb::MsMs 60773 Specdb::MsMs 117174 Specdb::MsMs 117175 Specdb::MsMs 117176 Specdb::MsMs 1471029 Specdb::MsMs 1476107 Specdb::MsMs 1476108 Specdb::MsMs 1476109 Specdb::MsMs 1476110 Specdb::MsMs 1476111 Specdb::MsMs 1476112 Specdb::MsMs 1476113 Specdb::MsMs 1476114 Specdb::MsMs 1476115 Specdb::MsMs 1476116 Specdb::MsMs 1476117 Specdb::MsMs 1476118 Specdb::MsMs 1476119 Specdb::MsMs 1476120 Specdb::MsMs 1476121 Specdb::MsMs 1476122 Specdb::MsMs 1476123 Specdb::MsMs 1476124 HMDB35089 15400 #<Reference:0x000055ce3011b968> #<Reference:0x000055ce3011b7b0> #<Reference:0x000055ce3011b5f8> Black tea Type 1 Blackberry Type 1 specific Rubus Caraway Type 1 specific Carum carvi 48032 Cornmint Type 1 specific Mentha arvensis 292239 Dill Type 1 specific Anethum graveolens 40922 Evergreen blackberry Type 1 specific Rubus laciniatus Green tea Type 1 Herbal tea Type 1 Herbs and Spices Unknown generic Peppermint Type 1 specific Mentha X piperita 34256 Red tea Type 1 Spearmint Type 1 specific Mentha spicata 29719 Tea Type 1 specific Camellia sinensis 4442 herbal mint minty spearmint sweet