1.0 2010-04-08 22:12:10 UTC 2020-09-17 15:30:28 UTC FDB015974 Piperitenone Piperitenone belongs to the class of organic compounds known as menthane 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, piperitenone is an isoprenoid lipid molecule. It is very hydrophobic, almost insoluble in water, and relatively neutral. Piperitenone is a minty, phenolic, and sharp-taste ( http://www.thegoodscentscompany.com/data/rw1031141.html). Piperitenone is found in highest concentrations in spearmints and rosemaries. It was detected in peppermints, herbs and spices, orange mints, citrus, and mentha (mint). This could make piperitenone a potential biomarker for the consumption of these foods. 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethylidene)- 3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one 3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one, 9CI 3-methyl-6-propan-2-ylidenecyclohex-2-en-1-one 3-Terpinolenone 6-Isopropylidene-3-methyl-2-cyclohexenone FEMA 3560 Piperitenone Pulespenone C10H14O 150.2176 150.10446507 3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one piperitenone 491-09-8 CC(C)=C1CCC(C)=CC1=O InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3 HKZQJZIFODOLFR-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 Cyclohexenones Hydrocarbon derivatives Monocyclic monoterpenoids O-quinomethanes Organic oxides Aliphatic homomonocyclic compound Carbonyl group Cyclic ketone Cyclohexenone Hydrocarbon derivative Ketone Monocyclic monoterpenoid O-quinomethane Organic oxide Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Quinomethane Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids a small molecule p-menthadien-3-one logp 2.39 ALOGPS logs -1.86 ALOGPS solubility 2.05e+00 g/l ALOGPS logp 2.81 ChemAxon pka_strongest_acidic 18.6 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac 3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one ChemAxon average_mass 150.2176 ChemAxon mono_mass 150.10446507 ChemAxon smiles CC(C)=C1CCC(C)=CC1=O ChemAxon formula C10H14O ChemAxon inchi InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3 ChemAxon inchikey HKZQJZIFODOLFR-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 47.96 ChemAxon polarizability 17.77 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 7344 Specdb::MsIr 7345 Specdb::MsMs 319384 Specdb::MsMs 319385 Specdb::MsMs 319386 Specdb::MsMs 366487 Specdb::MsMs 366488 Specdb::MsMs 366489 Specdb::MsMs 2274387 Specdb::MsMs 2274388 Specdb::MsMs 2274389 Specdb::MsMs 3091810 Specdb::MsMs 3091811 Specdb::MsMs 3091812 Specdb::CMs 24101 Specdb::CMs 162313 Specdb::NmrOneD 138130 Specdb::NmrOneD 138131 Specdb::NmrOneD 138132 Specdb::NmrOneD 138133 Specdb::NmrOneD 138134 Specdb::NmrOneD 138135 Specdb::NmrOneD 138136 Specdb::NmrOneD 138137 Specdb::NmrOneD 138138 Specdb::NmrOneD 138139 Specdb::NmrOneD 138140 Specdb::NmrOneD 138141 Specdb::NmrOneD 138142 Specdb::NmrOneD 138143 Specdb::NmrOneD 138144 Specdb::NmrOneD 138145 Specdb::NmrOneD 138146 Specdb::NmrOneD 138147 Specdb::NmrOneD 138148 Specdb::NmrOneD 138149 HMDB36999 17304 #<Reference:0x000055ce300b1478> #<Reference:0x000055ce300b12c0> Citrus Unknown generic Cornmint Type 1 specific Mentha arvensis 292239 Herbs and Spices Unknown generic Mentha Type 1 specific Mentha 21819 Orange mint Type 1 specific Mentha aquatica 190902 Peppermint Type 1 specific Mentha X piperita 34256 Rosemary Type 1 specific Rosmarinus officinalis 39367 0.6 0.6 0.6 mg/100 g Spearmint Type 1 specific Mentha spicata 29719 496.05 496.05 496.05 mg/100 g minty phenolic sharp 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. Perfumery 1206 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. Toxic 1371 A role played by the molecular entity or part thereof which causes the development of a pathological process.