Record Information
Version1.0
Creation date2010-04-08 22:10:47 UTC
Update date2018-05-29 01:06:04 UTC
Primary IDFDB013573
Secondary Accession Numbers
  • FDB029739
Chemical Information
FooDB NamePiperitone
DescriptionFlavouring ingredient 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. Piperitone is found in many foods, some of which are tamarind, cumin, rosemary, and wild celery.
CAS Number89-81-6
Structure
Thumb
Synonyms
SynonymSource
3-CarvomenthenoneChEBI
3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-oneChEBI
6-Isopropyl-3-methylcyclohex-2-enoneChEBI
p-Menth-1-en-3-oneChEBI
(+-)-PiperitoneHMDB
1-Methyl-4-isopropyl-1-cyclohexen-3-oneHMDB
3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-oneHMDB
6-Isopropyl-3-methyl-2-cyclohexen-1-oneHMDB
DL-PiperitoneHMDB
FEMA 2910HMDB
2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-biospider
3-methyl-6-(propan-2-yl)cyclohex-2-en-1-onebiospider
Piperitonedb_source
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP2.47ALOGPS
logP3ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)18.87ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.35 m³·mol⁻¹ChemAxon
Polarizability18.32 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16O
IUPAC name3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one
InChI IdentifierInChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3
InChI KeyYSTPAHQEHQSRJD-UHFFFAOYSA-N
Isomeric SMILESCC(C)C1CCC(C)=CC1=O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
Classification
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting Point< 25 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP2.85GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID6721
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6987
Pubchem Substance IDNot Available
ChEBI ID48933
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34975
CRC / DFC (Dictionary of Food Compounds) IDJFJ29-J:JFJ29-J
EAFUS IDNot Available
Dr. Duke IDPIPERITONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet ID89-81-6
GoodScent IDrw1049441
SuperScent IDNot Available
Wikipedia IDPiperitone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti asthmatic49167 A drug used to treat asthma.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mint
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fresh
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
minty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medicinal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).