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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:36:49 UTC
Update Date2022-03-07 02:54:34 UTC
HMDB IDHMDB0035604
Secondary Accession Numbers
  • HMDB0061794
  • HMDB35604
  • HMDB61794
Metabolite Identification
Common NamePulegone
DescriptionPulegone 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. It is formally classified as a cyclic ketone although it is biochemically a monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Pulegone is a hydrophobic, neutral compound that is insoluble in water. It exists as a clear, colorless oil. There are two isomers of Pulegone (the R and the S isomer), with the R isomer being more common. It is used industrially as a food additive and a perfuming agent. Pulegone has a fresh, minty or peppermint odor and a minty, fruity or green taste. It is found naturally in the essential oils of a variety of plants such as Nepeta cataria (catnip), Hedeoma pulegioides (pennyroyal), and Mentha species. It is also found in a number of plant foods and spices such as blackberryies, black currants, bell peppers, cornmint, rosemary, black tea, thyme, orange mint, peppermint, and spearmint, which makes it a potential biomarker for the consumption of these food products. Pulegone is also one of more than 140 terpenes that are found in cannabis plants (PMID:6991645 ).
Structure
Data?1563862744
Synonyms
ValueSource
(+)-(R)-PulegoneChEBI
(1R)-(+)-p-Menth-4(8)-en-3-oneChEBI
(5R)-2-Isopropylidene-5-methylcyclohexanoneChEBI
(R)-PulegoneChEBI
D-PulegoneChEBI
(+)-PulegoneKegg
Pulegone, (R)-isomerHMDB
(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
(R)-(+)-PulegoneHMDB
(1R)-PulegoneHMDB
L-PulegoneHMDB
NSC 15334HMDB
PulegonHMDB
FEMA 2963HMDB
(+)-4(8)-Para-menthen-3-oneHMDB
5-Methyl-2-(1-methylethylidene)cyclohexanoneHMDB
PulegoneChEBI
(5R)-5-Methyl-2-(1-methylethylidene)cyclohexanonePhytoBank
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
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point220.00 to 222.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility173.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.08Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.00731661259
DarkChem[M-H]-131.77731661259
DeepCCS[M+H]+141.24230932474
DeepCCS[M-H]-138.82130932474
DeepCCS[M-2H]-174.20830932474
DeepCCS[M+Na]+149.21130932474
AllCCS[M+H]+132.332859911
AllCCS[M+H-H2O]+127.832859911
AllCCS[M+NH4]+136.432859911
AllCCS[M+Na]+137.632859911
AllCCS[M-H]-137.332859911
AllCCS[M+Na-2H]-138.832859911
AllCCS[M+HCOO]-140.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PulegoneC[C@@H]1CCC(=C(C)C)C(=O)C11676.2Standard polar33892256
PulegoneC[C@@H]1CCC(=C(C)C)C(=O)C11242.7Standard non polar33892256
PulegoneC[C@@H]1CCC(=C(C)C)C(=O)C11239.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pulegone,1TMS,isomer #1CC(C)=C1CC[C@@H](C)C=C1O[Si](C)(C)C1410.3Semi standard non polar33892256
Pulegone,1TMS,isomer #1CC(C)=C1CC[C@@H](C)C=C1O[Si](C)(C)C1389.0Standard non polar33892256
Pulegone,1TBDMS,isomer #1CC(C)=C1CC[C@@H](C)C=C1O[Si](C)(C)C(C)(C)C1620.2Semi standard non polar33892256
Pulegone,1TBDMS,isomer #1CC(C)=C1CC[C@@H](C)C=C1O[Si](C)(C)C(C)(C)C1551.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Pulegone EI-B (Non-derivatized)splash10-0f89-9200000000-103da19d7e73140f53a72018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pulegone GC-EI-Q (Non-derivatized)splash10-0fsi-9300000000-5c40f6bc1c5dd5e64dc82020-07-08HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pulegone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0btm-9600000000-72752a4904dbe00f2b4a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pulegone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pulegone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0kur-9400000000-182826a9f81c661c74962015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pulegone 10V, Positive-QTOFsplash10-0udi-0900000000-50f4b6a38ec680e83d0c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pulegone 20V, Positive-QTOFsplash10-114i-6900000000-04a7ff4ee15b9b1c81612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pulegone 40V, Positive-QTOFsplash10-0ldi-9100000000-2aee3b73ef815011023f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pulegone 10V, Negative-QTOFsplash10-0udi-0900000000-cd90c558f842f253efd32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pulegone 20V, Negative-QTOFsplash10-0udi-0900000000-011197e33d9b4420c2572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pulegone 40V, Negative-QTOFsplash10-0a4u-6900000000-723bf6d0a35d2e10aafd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pulegone 10V, Positive-QTOFsplash10-0ik9-2900000000-7f3925a428ada570a2f62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pulegone 20V, Positive-QTOFsplash10-00l6-9300000000-2fd8486379bd720b7b382021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pulegone 40V, Positive-QTOFsplash10-0006-9000000000-441dfa2e182dd78429bc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pulegone 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pulegone 20V, Negative-QTOFsplash10-0udi-0900000000-9fc5f57a10d95a4f369b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pulegone 40V, Negative-QTOFsplash10-014i-5900000000-7ce0df14de5e9c637a482021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB030074
KNApSAcK IDC00000827
Chemspider ID390923
KEGG Compound IDC09893
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPulegone
METLIN IDNot Available
PubChem Compound442495
PDB IDNot Available
ChEBI ID35596
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006501
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. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  10. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  11. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  12. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  13. Wikipedia [Link]
  14. Wikipedia [Link]
  15. UniProt Q6WAU0 : (+)-pulegone reductase [Link]
  16. Robert Carson, 'Cosmetic skin care compositions containing pulegone.' U.S. Patent US20020006423, issued January 17, 2002. [Link]