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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:36:49 UTC
Update Date2019-07-23 06:19:04 UTC
HMDB IDHMDB0035604
Secondary Accession Numbers
  • HMDB0061794
  • HMDB35604
  • HMDB61794
Metabolite Identification
Common NamePulegone
DescriptionPulegone is a minty tasting naturally occurring organic compound found in cornmint, orange mint, peppermint, and spearmint, which makes it a potential biomarker for the consumption of these food products. It is classified as a monoterpene and is a fragrance and flavour ingredient. Pulegone is also found in blackcurrant and can be obtained from the essential oils of a variety of plants such as Nepeta cataria (catnip), Hedeoma pulegioides (pennyroyal), and Mentha species.
Structure
Data?1563862744
Synonyms
ValueSource
(+)-(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-oneCAS
(R)-p-Menth-4(8)-en-3-oneCAS
p-Menth-4(8)-en-3-oneCAS
(R)-5-methyl-2-(1-methylethylidene)cyclohexanoneCAS
(+)-PulegoneCAS
(R)-(+)-PulegoneCAS
(1R)-PulegoneCAS
L-PulegoneCAS
NSC 15334CAS
PulegonCAS
FEMA 2963HMDB
(+)-4(8)-para-Menthen-3-oneHMDB
5-Methyl-2-(1-methylethylidene)cyclohexanoneHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name(5R)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-one
Traditional Name(+)-pulegone
CAS Registry Number89-82-7
SMILES
C[C@@H]1CCC(=C(C)C)C(=O)C1
InChI Identifier
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1
InChI KeyNZGWDASTMWDZIW-MRVPVSSYSA-N
Chemical Taxonomy
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.08Not Available
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
Polarizability18.33 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f89-9200000000-103da19d7e73140f53a7JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0btm-9600000000-72752a4904dbe00f2b4aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-50f4b6a38ec680e83d0cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-114i-6900000000-04a7ff4ee15b9b1c8161JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldi-9100000000-2aee3b73ef815011023fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-cd90c558f842f253efd3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-011197e33d9b4420c257JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-6900000000-723bf6d0a35d2e10aafdJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0kur-9400000000-182826a9f81c661c7496JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030074
KNApSAcK IDC00000827
Chemspider IDNot Available
KEGG Compound IDC09893
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442495
PDB IDNot Available
ChEBI ID35596
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Madyastha KM, Gaikwad NW: Metabolic fate of S-(-)-pulegone in rat. Xenobiotica. 1998 Aug;28(8):723-34. [PubMed:9741951 ]
  2. Chen LJ, Lebetkin EH, Burka LT: Metabolism of (R)-(+)-pulegone in F344 rats. Drug Metab Dispos. 2001 Dec;29(12):1567-77. [PubMed:11717176 ]
  3. Yang JP, Bao BH, Zhang L, Ding AW: [Quantitative analysis of pulegone in Herba Schizonepetae]. Zhongguo Zhong Yao Za Zhi. 2005 May;30(9):669-70. [PubMed:16075729 ]
  4. Dancewicz K, Gabrys B, Dams I, Wawrzenczyk C: Enantiospecific effect of pulegone and pulegone-derived lactones on Myzus persicae (Sulz.) settling and feeding. J Chem Ecol. 2008 Apr;34(4):530-8. doi: 10.1007/s10886-008-9448-9. Epub 2008 Mar 14. [PubMed:18340487 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  9. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  11. Wikipedia [Link]
  12. Wikipedia [Link]
  13. UniProt Q6WAU0 : (+)-pulegone reductase [Link]
  14. Robert Carson, 'Cosmetic skin care compositions containing pulegone.' U.S. Patent US20020006423, issued January 17, 2002. [Link]