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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:08:55 UTC
Update Date2022-03-07 02:54:46 UTC
HMDB IDHMDB0036079
Secondary Accession Numbers
  • HMDB36079
Metabolite Identification
Common NameDihydrocarvone
DescriptionDihydrocarvone, also known as menth-8-en-2-one, 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. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes in plants is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Dihydrocarvone is an essentially neutral compound. It has a warm herbal, minty taste with a spicy minty woody camphoreous flavour ( Ref:DOI ). Dihydrocarvone is found in highest concentrations in spearmints, caraway, and wild celeries and was detected celery stalks, dills, pepper (spice), and peppermints. This could make dihydrocarvone a potential biomarker for the consumption of these foods. Dihydrocarvone is also found in cannabis plants (PMID:6991645 ).
Structure
Data?1563862818
Synonyms
ValueSource
2-Methyl-5-(1-methylethenyl)cyclohexanoneChEBI
2-Methyl-5-isopropenylcyclohexanoneChEBI
5-Isopropenyl-2-methylcyclohexanoneChEBI
8-p-Menthen-2-oneChEBI
Menth-8-en-2-oneChEBI
p-Menth-8(9)-en-2-oneChEBI
3-Isopropenyl-6-methylcyclohexanoneMeSH
p-Menth-8-en-2-oneMeSH
a DihydrocarvoneChEBI, HMDB
1,6-DihydrocarvoneHMDB
2-Methyl-5-(1-methylethenyl)-cyclohexanoneHMDB
2-Methyl-5-(1-methylethenyl)cyclohexanone, 9ciHMDB
2-Methyl-5-(1-methylvinyl)cyclohexan-1-oneHMDB
2-Methyl-5-(prop-1-en-2-yl)cyclohexanoneHMDB
FEMA 3565HMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one
Traditional Namedihydrocarvone
CAS Registry Number7764-50-3
SMILES
CC1CCC(CC1=O)C(C)=C
InChI Identifier
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3
InChI KeyAZOCECCLWFDTAP-UHFFFAOYSA-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

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point87.00 to 88.00 °C. @ 6.00 mm HgThe Good Scents Company Information System
Water Solubility1.02 mg/mL at 15 °CNot Available
LogP2.85Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
logP2.39ALOGPS
logP2.7ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.3 m³·mol⁻¹ChemAxon
Polarizability18.27 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]+135.66931661259
DarkChem[M-H]-128.89331661259
DeepCCS[M+H]+141.01630932474
DeepCCS[M-H]-137.26930932474
DeepCCS[M-2H]-174.77330932474
DeepCCS[M+Na]+150.23230932474
AllCCS[M+H]+132.732859911
AllCCS[M+H-H2O]+128.232859911
AllCCS[M+NH4]+136.932859911
AllCCS[M+Na]+138.132859911
AllCCS[M-H]-137.032859911
AllCCS[M+Na-2H]-138.632859911
AllCCS[M+HCOO]-140.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DihydrocarvoneCC1CCC(CC1=O)C(C)=C1663.1Standard polar33892256
DihydrocarvoneCC1CCC(CC1=O)C(C)=C1159.5Standard non polar33892256
DihydrocarvoneCC1CCC(CC1=O)C(C)=C1201.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydrocarvone,1TMS,isomer #1C=C(C)C1CCC(C)=C(O[Si](C)(C)C)C11364.8Semi standard non polar33892256
Dihydrocarvone,1TMS,isomer #1C=C(C)C1CCC(C)=C(O[Si](C)(C)C)C11350.5Standard non polar33892256
Dihydrocarvone,1TMS,isomer #2C=C(C)C1C=C(O[Si](C)(C)C)C(C)CC11308.8Semi standard non polar33892256
Dihydrocarvone,1TMS,isomer #2C=C(C)C1C=C(O[Si](C)(C)C)C(C)CC11320.4Standard non polar33892256
Dihydrocarvone,1TBDMS,isomer #1C=C(C)C1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C11599.6Semi standard non polar33892256
Dihydrocarvone,1TBDMS,isomer #1C=C(C)C1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C11530.5Standard non polar33892256
Dihydrocarvone,1TBDMS,isomer #2C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)CC11550.8Semi standard non polar33892256
Dihydrocarvone,1TBDMS,isomer #2C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)CC11489.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrocarvone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00m3-9100000000-fa9716dc62a7dad687482017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrocarvone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0159-9200000000-204b096f608a1da059c52015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocarvone 10V, Positive-QTOFsplash10-0udi-1900000000-11c8140e07776f4ec8a82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocarvone 20V, Positive-QTOFsplash10-0zfr-9700000000-aa93539a6a6d13e993c52015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocarvone 40V, Positive-QTOFsplash10-100r-9000000000-2654db8ab644e23609132015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocarvone 10V, Negative-QTOFsplash10-0udi-0900000000-869565234ac5daf7c3b22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocarvone 20V, Negative-QTOFsplash10-0udi-0900000000-66279fba8a75e05ec84b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocarvone 40V, Negative-QTOFsplash10-0kto-9500000000-19dd52dd1ac87fa23abf2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocarvone 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocarvone 20V, Negative-QTOFsplash10-0udi-1900000000-6d20364e296745592a692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocarvone 40V, Negative-QTOFsplash10-00kn-6900000000-23186e60d8ffad6745272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocarvone 10V, Positive-QTOFsplash10-0gws-7900000000-b08efab8959a09a262162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocarvone 20V, Positive-QTOFsplash10-000x-9200000000-13ccbe770389182b9c062021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrocarvone 40V, Positive-QTOFsplash10-0006-9000000000-4b6afc70d0efd7f97f152021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDFDB014914
KNApSAcK IDC00010947
Chemspider ID22881
KEGG Compound IDC18018
BioCyc IDDihydrocarvones
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24473
PDB IDNot Available
ChEBI ID23733
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1031221
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.