1.02010-04-08 22:11:17 UTC2019-11-26 03:10:06 UTCFDB014466(R)-PiperitoneConstituent of Mentha subspecies and Zanthoxylum piperitum (Japanese pepper tree) oil
Piperitone is a natural monoterpene ketone which is a component of some essential oils. Both stereoisomers, the D-form and the L-form, are known. The D-form has a peppermint-like aroma and has been isolated from the oils of plants from the genera Cymbopogon, Andropogon, and Mentha. The L-form has been isolated from Sitka spruce. (R)-Piperitone is found in cornmint, spearmint, and herbs and spices.(-)-Piperitone(6R)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one(6R)-3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-one(6R)-6-Isopropyl-3-methylcyclohex-2-en-1-one(R)-6-(Isopropyl)-3-methylcyclohex-2-en-1-oneL-PiperitoneC10H16O152.2334152.120115134(6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-oneα-piperitone4573-50-6CC(C)[C@@H]1CCC(C)=CC1=OInChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3/t9-/m0/s1YSTPAHQEHQSRJD-VIFPVBQESA-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 monoterpenoidsOrganic compoundsLipids and lipid-like moleculesPrenol lipidsMonoterpenoidsAliphatic homomonocyclic compoundsCyclohexenonesHydrocarbon derivativesMonocyclic monoterpenoidsOrganic oxidesAliphatic homomonocyclic compoundCarbonyl groupCyclic ketoneCyclohexenoneHydrocarbon derivativeKetoneMonocyclic monoterpenoidOrganic oxideOrganic oxygen compoundOrganooxygen compoundP-menthane monoterpenoidCyclic monoterpenesMenthane monoterpenoidsMenthane monoterpenoidspiperitonelogp2.47logs-2.05solubility1.36e+00 g/lmelting_pointMp -29°logp3pka_strongest_acidic18.87pka_strongest_basic-4.6iupac(6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-oneaverage_mass152.2334mono_mass152.120115134smilesCC(C)[C@@H]1CCC(C)=CC1=OformulaC10H16OinchiInChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3/t9-/m0/s1inchikeyYSTPAHQEHQSRJD-VIFPVBQESA-Npolar_surface_area17.07refractivity47.35polarizability18.32rotatable_bond_count1acceptor_count1donor_count0physiological_charge0formal_charge0Specdb::CMs15915Specdb::CMs135702Specdb::CMs143436Specdb::CMs168968Specdb::MsMs101382Specdb::MsMs101383Specdb::MsMs101384Specdb::MsMs166998Specdb::MsMs166999Specdb::MsMs167000Specdb::MsMs2336728Specdb::MsMs2336729Specdb::MsMs2336730Specdb::MsMs2432905Specdb::MsMs2432906Specdb::MsMs2432907HMDB3573748934#<Reference:0x0000555675bc2458>CornmintType 1specificMentha arvensis292239397.0397.0397.0mg/100 gHerbs and SpicesUnknowngenericSpearmintType 1specificMentha spicata2971931.231.231.2mg/100 gmintypeppermintpungentanti acetylcholinesterase76An 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.