Record Information
Version1.0
Creation date2010-04-08 22:10:47 UTC
Update date2019-11-26 03:08:38 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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPiperitone, non-derivatized, GC-MS Spectrumsplash10-01qi-9300000000-f92830f958dd7b7816c0Spectrum
GC-MSPiperitone, non-derivatized, GC-MS Spectrumsplash10-01qi-9300000000-f92830f958dd7b7816c0Spectrum
Predicted GC-MSPiperitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kf-9300000000-e3bec6231e4993e3d578Spectrum
Predicted GC-MSPiperitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-0f2176d975b2f9bfe7fd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-7900000000-bc07a247759df113c9432016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-6e8d2587c3fab7a87b032016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-83fb585962f6ed48b3782016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-a2b215f78ea2edceb56c2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-8900000000-058070ac2054c97f9a302016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-1900000000-cf5ff8ec6a34a5b6435b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-9200000000-ddaec970d54edc7cbf792021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-4c75828fad35f0eec3742021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-3f9a24ef7ca3da32a5222021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9400000000-172af5b361384699caf72021-09-25View Spectrum
NMRNot Available
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
Food Biomarker OntologyNot Available
VMH 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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
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).