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Showing Compound Isopulegone (FDB014368)

Record Information
Version1.0
Creation date2010-04-08 22:11:14 UTC
Update date2025-11-19 00:45:55 UTC
Primary IDFDB014368
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsopulegone
Description(-)-trans-isopulegone, also known as isopulegone or 1-methyl-4-isopropenyl-3-cyclohexanone, 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 (-)-trans-isopulegone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (-)-trans-isopulegone can be found in fats and oils, which makes (-)-trans-isopulegone a potential biomarker for the consumption of this food product.
CAS Number529-00-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-Methyl-4-isopropenyl-3-cyclohexanoneChEBI
IsopulegoneChEBI
(+)-IsopulegoneHMDB
(-)-trans-P-Menth-8-en-3-oneHMDB
(2R-trans)-5-Methyl-2-(1-methylethenyl)-cyclohexanoneHMDB
Pulegone, (S)-isomerMeSH, HMDB
Pulegone, (R)-isomerMeSH, HMDB
PulegoneMeSH, HMDB
cis-IsopulegoneMeSH, HMDB
2-Isopropenyl-5-methylcyclohexanonedb_source
5-Methyl-2-(1-methylethenyl)cyclohexanonedb_source
a-Pulegonedb_source
p-Menth-8-en-3-onedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP2.42ALOGPS
logP2.7ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)17.88ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.3 m³·mol⁻¹ChemAxon
Polarizability18.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16O
IUPAC name5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one
InChI IdentifierInChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-9H,1,4-6H2,2-3H3
InChI KeyRMIANEGNSBUGDJ-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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(+)-cis-Isopulegone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9200000000-f21ebfb4bb2675e3ee84Spectrum
Predicted GC-MS(+)-cis-Isopulegone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-86c22d1bcbce97c1118d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-11or-7900000000-60e1710999312dfb06862015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvl-9100000000-eb59a6a329c31dd90fd92015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-a78fe6479a5d6949a0742015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-006545b22bbfa3933fdb2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rx-9700000000-20b227005a182a5395222015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3900000000-8f6da06f8b0ab70ada652021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015c-9200000000-d3bd3bc742e7ae79c7e92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-eddd98ab96727b2ed6632021-09-22View 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-0900000000-7c68a150979e2bd9e7982021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5900000000-6e9f773c05f9e65828bf2021-09-22View Spectrum
NMRNot Available
ChemSpider ID31884
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID34645
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0035741
CRC / DFC (Dictionary of Food Compounds) IDJPW05-E:JPW05-E
EAFUS ID1940
Dr. Duke IDTRANS-ISOPULEGONE|ISOPULEGONE
BIGG IDNot Available
KNApSAcK IDC00010948
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1034221
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
Name48318 flavorDUKE
Hepatotoxic50908 An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy.DUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.DUKE
Pulmonotoxic52209 An agent that damages or harms the lungs, often used to describe substances or drugs with toxic effects on pulmonary tissue, limiting its therapeutic applications but aiding in understanding lung disease mechanisms and developing protective strategies.DUKE
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.
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  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).