Record Information
Version1.0
Creation date2010-04-08 22:11:11 UTC
Update date2019-11-26 03:09:48 UTC
Primary IDFDB014298
Secondary Accession Numbers
  • FDB014299
Chemical Information
FooDB Name(R)-p-Menth-4(8)-en-3-one
Description(R)-p-Menth-4(8)-en-3-one, also known as (+-)-pulegone or isopulegone, 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 (R)-p-Menth-4(8)-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number89-82-7
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility2.29 g/LALOGPS
logP2.36ALOGPS
logP2.86ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.13 m³·mol⁻¹ChemAxon
Polarizability18.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16O
IUPAC name5-methyl-2-(propan-2-ylidene)cyclohexan-1-one
InChI IdentifierInChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3
InChI KeyNZGWDASTMWDZIW-UHFFFAOYSA-N
Isomeric SMILESCC1CCC(=C(C)C)C(=O)C1
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
  • 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
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(R)-p-Menth-4(8)-en-3-one, non-derivatized, GC-MS Spectrumsplash10-0f89-9200000000-103da19d7e73140f53a7Spectrum
Predicted GC-MS(R)-p-Menth-4(8)-en-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0btm-9600000000-2638fe5c4d411ceee0dcSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-50f4b6a38ec680e83d0c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-114i-6900000000-7e29b900e574c214c8cb2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldi-9100000000-cb8b1a6e7185079672ba2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-cd90c558f842f253efd32015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-011197e33d9b4420c2572015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-6900000000-723bf6d0a35d2e10aafd2015-05-27View Spectrum
NMRNot Available
ChemSpider ID6722
ChEMBL IDNot Available
KEGG Compound IDC09893
Pubchem Compound ID6988
Pubchem Substance IDNot Available
ChEBI ID35596
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35604
CRC / DFC (Dictionary of Food Compounds) IDJPJ96-T:JPJ72-J
EAFUS ID3254
Dr. Duke IDPULEGONE
BIGG IDNot Available
KNApSAcK IDC00000827
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1006501
SuperScent ID442495
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
BlackcurrantExpected but not quantifiedNot AvailableDUKE
Cornmint1253.000 - 1253.000 mg/100 g1253.000 mg/100 gDUKE
Green bell pepperExpected but not quantifiedNot AvailableDUKE
Highbush blueberryExpected but not quantifiedNot AvailableDUKE
MenthaExpected but not quantifiedNot AvailableKNAPSACK
Orange bell pepperExpected but not quantifiedNot AvailableDUKE
Orange mint0.01000 - 10.35000 mg/100 g5.180 mg/100 gDUKE
PepperExpected but not quantifiedNot AvailableDUKE
Pepper (C. frutescens)Expected but not quantifiedNot AvailableDUKE
Peppermint326.650 - 326.650 mg/100 g326.650 mg/100 gDUKE
Showing 1 to 10 of 13 entries
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.