Record Information
Version1.0
Creation date2010-04-08 22:11:11 UTC
Update date2018-05-29 01:10:58 UTC
Primary IDFDB014299
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namep-Menth-4(8)-en-3-one
DescriptionP-menth-4(8)-en-3-one, also known as (+-)-pulegone or isopulegone, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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. P-menth-4(8)-en-3-one is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). P-menth-4(8)-en-3-one is a minty tasting compound found in cornmint, orange mint, peppermint, and spearmint, which makes P-menth-4(8)-en-3-one a potential biomarker for the consumption of these food products. P-menth-4(8)-en-3-one is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as Nepeta cataria (catnip), Mentha piperita, and pennyroyal. It is classified as a monoterpene .
CAS Number15932-80-6
Structure
Thumb
Synonyms
SynonymSource
(+)-(R)-PulegoneChEBI
(1R)-(+)-P-Menth-4(8)-en-3-oneChEBI
(5R)-2-Isopropylidene-5-methylcyclohexanoneChEBI
(R)-PulegoneChEBI
D-PulegoneChEBI
PulegoneChEBI
Pulegone, (R)-isomerMeSH
(R)-(+)-p-Menth-4(8)-en-3-oneHMDB
(R)-p-Menth-4(8)-en-3-oneHMDB
p-Menth-4(8)-en-3-oneHMDB
(R)-5-methyl-2-(1-methylethylidene)cyclohexanoneHMDB
(+)-PulegoneHMDB
(R)-(+)-PulegoneHMDB
(1R)-PulegoneHMDB
L-PulegoneHMDB
NSC 15334HMDB
PulegonHMDB
FEMA 2963HMDB
(+)-4(8)-para-Menthen-3-oneHMDB
5-Methyl-2-(1-methylethylidene)cyclohexanoneHMDB
(+)-pulegonbiospider
2-Isopropylidene-5-methylcyclohexanonedb_source
b-Pulegonedb_source
Pulegonesbiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
DescriptionThis compound 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
Physico-Chemical Properties - Experimental
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 PointNot Available
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 Key
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID26381
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJPJ96-T:JPJ96-T
EAFUS IDNot Available
Dr. Duke ID(+)-PULEGONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1507831
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
irritantDUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).