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Record Information
Version3.6
Creation Date2012-09-11 19:54:33 UTC
Update Date2016-02-11 02:35:26 UTC
HMDB IDHMDB34975
Secondary Accession NumbersNone
Metabolite Identification
Common NamePiperitone
DescriptionPiperitone is found in ceylan cinnamon. Piperitone is a flavouring 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. (Wikipedia) Piperitone belongs to the family of Monocyclic Monoterpenes. These are monoterpenes containing 1 ring in the isoprene chain.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one
Traditional Namepiperitone
CAS Registry Number89-81-6
SMILES
CC(C)C1CCC(C)=CC1=O
InChI Identifier
InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3
InChI KeyInChIKey=YSTPAHQEHQSRJD-UHFFFAOYNA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient
Application
  • Flavoring Agent
  • Nutrient
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.85Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.36 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.35 m3·mol-1ChemAxon
Polarizability18.32 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB013573
KNApSAcK IDNot Available
Chemspider ID6721
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiperitone
NuGOwiki LinkHMDB34975
Metagene LinkHMDB34975
METLIN IDNot Available
PubChem Compound6987
PDB IDNot Available
ChEBI ID48933
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.