Record Information
Version1.0
Creation date2010-04-08 22:12:10 UTC
Update date2018-05-29 18:28:27 UTC
Primary IDFDB015974
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePiperitenone
DescriptionPiperitenone, also known as 3-terpinolenone or fema 3560, 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. Thus, piperitenone is considered to be an isoprenoid lipid molecule. Piperitenone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number491-09-8
Structure
Thumb
Synonyms
SynonymSource
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-oneHMDB
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one, 9ciHMDB
3-Methyl-6-propan-2-ylidenecyclohex-2-en-1-oneHMDB
3-TerpinolenoneHMDB
6-Isopropylidene-3-methyl-2-cyclohexenoneHMDB
FEMA 3560HMDB
PulespenoneHMDB
2-Cyclohexen-1-one, 3-methyl-6-(1-methylethylidene)-biospider
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one, 9CIdb_source
3-methyl-6-propan-2-ylidenecyclohex-2-en-1-onebiospider
Piperitenonedb_source
Predicted Properties
PropertyValueSource
Water Solubility2.05 g/LALOGPS
logP2.39ALOGPS
logP2.81ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)18.6ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.96 m³·mol⁻¹ChemAxon
Polarizability17.77 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H14O
IUPAC name3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one
InChI IdentifierInChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3
InChI KeyHKZQJZIFODOLFR-UHFFFAOYSA-N
Isomeric SMILESCC(C)=C1CCC(C)=CC1=O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
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
  • Quinomethane
  • O-quinomethane
  • 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:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 79.96%; H 9.39%; O 10.65%DFC
Melting PointNot Available
Boiling PointBp14 120-122°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f7c-8900000000-f5b1034f0ad5612f0f1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-c4031753132982c55fabJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-7900000000-9a0d9372d2684846d39bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-82fba962be7e9686c517JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-b7c0004066c195aa4089JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-49abeb92134d82dda90eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053s-2900000000-fba0f16e8603dd89ee04JSpectraViewer
ChemSpider ID337757
ChEMBL IDCHEMBL54161
KEGG Compound IDC01951
Pubchem Compound ID381152
Pubchem Substance IDNot Available
ChEBI ID17304
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36999
CRC / DFC (Dictionary of Food Compounds) IDKLQ60-W:KLQ60-W
EAFUS ID3055
Dr. Duke ID(+)-PIPERITENONE|PIPERITENONE
BIGG IDNot Available
KNApSAcK IDC00010889
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1031141
SuperScent IDNot Available
Wikipedia IDNot Available
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 acetylcholinesterase38462 An 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.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
toxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sharp
  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.
phenolic
  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).