Showing Compound Card for Pulegone (CDB000348)

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Record Information
Version1.0
Created at2020-03-19 00:32:15 UTC
Updated at2020-12-07 19:07:22 UTC
CannabisDB IDCDB000348
Secondary Accession NumbersNot Available
Cannabis Compound 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
Thumb
MOLSDFPDBSMILESInChI
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 Weight152.23
Monoisotopic Molecular Weight152.1201
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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point224 °CWikipedia
Water SolubilityNot AvailableNot Available
logP3.08Not Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0kur-9400000000-182826a9f81c661c74962015-03-01View Spectrum
GC-MSPulegone , non-derivatized, GC-MS Spectrumsplash10-0f89-9200000000-103da19d7e73140f53a7Spectrum
GC-MSPulegone , non-derivatized, GC-MS Spectrumsplash10-0fsi-9300000000-5c40f6bc1c5dd5e64dc8Spectrum
Predicted GC-MSPulegone , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0btm-9600000000-72752a4904dbe00f2b4aSpectrum
Predicted GC-MSPulegone , non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPulegone , non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-50f4b6a38ec680e83d0c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-114i-6900000000-04a7ff4ee15b9b1c81612016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldi-9100000000-2aee3b73ef815011023f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-cd90c558f842f253efd32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-011197e33d9b4420c2572016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-6900000000-723bf6d0a35d2e10aafd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ik9-2900000000-7f3925a428ada570a2f62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00l6-9300000000-2fd8486379bd720b7b382021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-441dfa2e182dd78429bc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-9fc5f57a10d95a4f369b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5900000000-7ce0df14de5e9c637a482021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035604
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  2. 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 ]