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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:08:58 UTC
Update Date2022-03-07 02:54:46 UTC
HMDB IDHMDB0036080
Secondary Accession Numbers
  • HMDB36080
Metabolite Identification
Common Name(1S,4S)-Dihydrocarvone
Description(1S,4S)-Dihydrocarvone 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. Thus, (1S,4S)-dihydrocarvone is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (1S,4S)-Dihydrocarvone.
Structure
Data?1563862818
Synonyms
ValueSource
(2S,5S)-2-Methyl-5-isopropenylcyclohexanoneChEBI
(2S,5S)-5-Isopropenyl-2-methylcyclohexanoneChEBI
(-)-DihydrocarvoneHMDB
(-)-trans-DihydrocarvoneHMDB
1S,4S-DihydrocarvoneHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name(2S,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one
Traditional Name(-)-dihydrocarvone
CAS Registry Number6909-25-7
SMILES
C[C@H]1CC[C@@H](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/t8-,9-/m0/s1
InChI KeyAZOCECCLWFDTAP-IUCAKERBSA-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 Point74.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling PointNot AvailableNot Available
Water Solubility273.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot 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]+137.55231661259
DarkChem[M-H]-132.49231661259
DeepCCS[M+H]+141.95430932474
DeepCCS[M-H]-139.55930932474
DeepCCS[M-2H]-173.85530932474
DeepCCS[M+Na]+148.45430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(1S,4S)-DihydrocarvoneC[C@H]1CC[C@@H](CC1=O)C(C)=C1631.3Standard polar33892256
(1S,4S)-DihydrocarvoneC[C@H]1CC[C@@H](CC1=O)C(C)=C1164.3Standard non polar33892256
(1S,4S)-DihydrocarvoneC[C@H]1CC[C@@H](CC1=O)C(C)=C1191.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(1S,4S)-Dihydrocarvone,1TMS,isomer #1C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C)C11368.3Semi standard non polar33892256
(1S,4S)-Dihydrocarvone,1TMS,isomer #1C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C)C11353.2Standard non polar33892256
(1S,4S)-Dihydrocarvone,1TMS,isomer #2C=C(C)[C@@H]1C=C(O[Si](C)(C)C)[C@@H](C)CC11305.4Semi standard non polar33892256
(1S,4S)-Dihydrocarvone,1TMS,isomer #2C=C(C)[C@@H]1C=C(O[Si](C)(C)C)[C@@H](C)CC11353.4Standard non polar33892256
(1S,4S)-Dihydrocarvone,1TBDMS,isomer #1C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C11603.3Semi standard non polar33892256
(1S,4S)-Dihydrocarvone,1TBDMS,isomer #1C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C11528.8Standard non polar33892256
(1S,4S)-Dihydrocarvone,1TBDMS,isomer #2C=C(C)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C)CC11540.5Semi standard non polar33892256
(1S,4S)-Dihydrocarvone,1TBDMS,isomer #2C=C(C)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C)CC11504.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (1S,4S)-Dihydrocarvone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00m3-9100000000-fa9716dc62a7dad687482017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (1S,4S)-Dihydrocarvone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (1S,4S)-Dihydrocarvone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 10V, Positive-QTOFsplash10-0udi-1900000000-8861ba576d835c24c4e22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 20V, Positive-QTOFsplash10-0zfr-9700000000-7b7dfb5b5671e2efed192016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 40V, Positive-QTOFsplash10-100r-9000000000-02b93dd813cef67449112016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 10V, Negative-QTOFsplash10-0udi-0900000000-3bdcde43911faafba8b72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 20V, Negative-QTOFsplash10-0udi-0900000000-66279fba8a75e05ec84b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 40V, Negative-QTOFsplash10-05n3-9500000000-02a124dc8509d82c4bb82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 10V, Positive-QTOFsplash10-0gws-7900000000-b08efab8959a09a262162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 20V, Positive-QTOFsplash10-000x-9200000000-13ccbe770389182b9c062021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 40V, Positive-QTOFsplash10-0006-9000000000-4b6afc70d0efd7f97f152021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 20V, Negative-QTOFsplash10-0udi-1900000000-6d20364e296745592a692021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 40V, Negative-QTOFsplash10-00kn-6900000000-23186e60d8ffad6745272021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB014916
KNApSAcK IDC00010947
Chemspider ID391455
KEGG Compound IDC11415
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443183
PDB IDNot Available
ChEBI ID168
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1054071
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.