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Showing Compound (S)-Piperitone (FDB014467)

Record Information
Version1.0
Creation date2010-04-08 22:11:17 UTC
Update date2019-11-26 03:10:07 UTC
Primary IDFDB014467
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-Piperitone
DescriptionCommon constituent of Mentha subspecies oils 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. (S)-Piperitone is found in mentha (mint), cornmint, and herbs and spices.
CAS Number6091-50-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(S)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-oneChEBI
(S)-PiperitoneChEBI
alpha-PiperitoneChEBI
D-PiperitoneChEBI
a-PiperitoneGenerator
Α-piperitoneGenerator
(-)-PiperitoneHMDB
(6R)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-oneHMDB
(6R)-3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-oneHMDB
(6R)-6-Isopropyl-3-methylcyclohex-2-en-1-oneHMDB
L-PiperitoneHMDB
(+)-Piperitonebiospider
(6S)-3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-onebiospider
2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (S)-biospider
3-Methyl-6-(1-methylethyl)-(S)-2-cyclohexen-1-oneHMDB
3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one, (S)-biospider
α-piperitoneGenerator
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 name(6S)-3-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/t9-/m0/s1
InChI KeyYSTPAHQEHQSRJD-VIFPVBQESA-N
Isomeric SMILESCC(C)[C@@H]1CCC(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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointNot Available
Boiling PointBp20 116-118.5°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +49.13DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(R)-Piperitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kf-9300000000-e3bec6231e4993e3d578Spectrum
Predicted GC-MS(R)-Piperitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(R)-Piperitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(R)-Piperitone, 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-0900000000-83fb585962f6ed48b3782016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-a2b215f78ea2edceb56c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-8900000000-058070ac2054c97f9a302016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-1900000000-cf5ff8ec6a34a5b6435b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-9200000000-ddaec970d54edc7cbf792021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-4c75828fad35f0eec3742021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-3f9a24ef7ca3da32a5222021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9400000000-172af5b361384699caf72021-09-22View Spectrum
NMRNot Available
ChemSpider ID55294
ChEMBL IDNot Available
KEGG Compound IDC09885
Pubchem Compound ID61362
Pubchem Substance IDNot Available
ChEBI ID41
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35738
CRC / DFC (Dictionary of Food Compounds) IDJFJ29-J:JQZ91-X
EAFUS ID3057
Dr. Duke ID(+)-PIPERITONE
BIGG IDNot Available
KNApSAcK IDC00003054
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1002881
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
peppermint
  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.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).