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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:01:58 UTC
Update Date2022-03-07 02:54:21 UTC
HMDB IDHMDB0035089
Secondary Accession Numbers
  • HMDB35089
Metabolite Identification
Common Name(R)-Carvone
DescriptionCarvone, with R and S isomers, also known as carvol or limonen-6-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. Carvone is a neutral compound. Carvone is a naturally occurring organic compound found in many essential oils but is most abundant in the oils from caraway seeds (Carum carvi), spearmint (Mentha spicata), and dill (PMID:27427817 ). Carvone is a volatile terpenoid found in cannabis plants (PMID:6991645 ). Carvone is occasionally found as a component of biological fluids in normal individuals. Both carvones (R, S) are used in the food and flavor industry (http//doi:10.1016/j.foodchem.2005.01.003). R-carvone is also used in air freshening products and in essential oils used in aromatherapy and alternative medicine. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841 (PMID:5556886 , 2477620 ). Carvone may help in the management of diseases (PMID:30374904 ) and had been considered as an adjuvant for treatment of cancer patients (PMID:30087792 ) and patients with epilepsy (PMID:31239862 ). It also has been successfully used as a biopesticide (PMID:30250476 ).
Structure
Data?1563862663
Synonyms
ValueSource
(-)-(4R)-CarvoneChEBI
(-)-(R)-CarvoneChEBI
(-)-p-Mentha-6,8-dien-2-oneChEBI
(4R)-CarvoneChEBI
(5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(R)-(-)-CarvoneChEBI
(R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(R)-5-Isopropenyl-2-methylcyclohex-2-en-1-oneChEBI
L-1-Methyl-4-isopropenyl-6-cyclohexen-2-oneChEBI
L-CarvoneChEBI
L-p-Mentha-1(6),8-dien-2-oneChEBI
Levo-carvoneChEBI
(-)-CarvoneHMDB
(4R)-(-)-CarvoneHMDB
(R)-(-)-P-Mentha-6,8-dien-2-oneHMDB
2-Methyl-5-(1-methylethenyl)-(R)-2-cyclohexen-1-oneHMDB
L(-)-CarvoneHMDB
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name(5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional Name(-)-carvone
CAS Registry Number6485-40-1
SMILES
CC(=C)[C@@H]1CC=C(C)C(=O)C1
InChI Identifier
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1
InChI KeyULDHMXUKGWMISQ-SECBINFHSA-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
  • Cyclohexenone
  • 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
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 15 °CNot Available
Boiling Point227.00 to 230.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.31 mg/mL at 25 °CNot Available
LogP2.71Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.16 g/LALOGPS
logP2.77ALOGPS
logP2.55ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.17 m³·mol⁻¹ChemAxon
Polarizability17.65 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]+136.61231661259
DarkChem[M-H]-132.84531661259
DeepCCS[M+H]+138.69430932474
DeepCCS[M-H]-136.31830932474
DeepCCS[M-2H]-171.49830932474
DeepCCS[M+Na]+146.4930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-CarvoneCC(=C)[C@@H]1CC=C(C)C(=O)C11751.2Standard polar33892256
(R)-CarvoneCC(=C)[C@@H]1CC=C(C)C(=O)C11211.4Standard non polar33892256
(R)-CarvoneCC(=C)[C@@H]1CC=C(C)C(=O)C11226.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-Carvone,1TMS,isomer #1C=C(C)[C@H]1C=C(O[Si](C)(C)C)C(C)=CC11385.2Semi standard non polar33892256
(R)-Carvone,1TMS,isomer #1C=C(C)[C@H]1C=C(O[Si](C)(C)C)C(C)=CC11361.3Standard non polar33892256
(R)-Carvone,1TBDMS,isomer #1C=C(C)[C@H]1C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC11615.6Semi standard non polar33892256
(R)-Carvone,1TBDMS,isomer #1C=C(C)[C@H]1C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC11537.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (R)-Carvone EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-Carvone EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-Carvone EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-Carvone EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418a2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Carvone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f83-9200000000-e9569993e9ab3a8d9c562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Carvone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Carvone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0f8c-9200000000-88f46d943b306bc533db2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Quattro_QQQ , positive-QTOF (Annotated)splash10-052f-9600000000-9902205f6d338c08818d2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 1V, positive-QTOFsplash10-0udi-0900000000-52f6355f33c4b2243d8a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 2V, positive-QTOFsplash10-0udi-0900000000-cb6bd893e3059c4e749a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 2V, positive-QTOFsplash10-0udi-0900000000-12445f07d9581bb79ba92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 3V, positive-QTOFsplash10-0zfr-0900000000-f9115bab64084ca3e9c62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 3V, positive-QTOFsplash10-0zfr-0900000000-c2cc2f68aa635d48f7d22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 3V, positive-QTOFsplash10-0pb9-0900000000-34673104b5cbea631cca2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 4V, positive-QTOFsplash10-0a4i-0900000000-3c5bc016004147d81ac12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 5V, positive-QTOFsplash10-0a4i-0900000000-805c8d6f02a70e4d8ced2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 6V, positive-QTOFsplash10-0a4i-1900000000-90f1a3149285030d18d32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 8V, positive-QTOFsplash10-0a4i-4900000000-c900c93dbadd576b2e032020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 9V, positive-QTOFsplash10-0a4l-9700000000-ccd0df21a8aba540288c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 11V, positive-QTOFsplash10-052f-9400000000-b05876718fef3d10e1e62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone Orbitrap 14V, positive-QTOFsplash10-00kf-9200000000-97e06bb63f72b6a871e62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone n/a 10V, positive-QTOFsplash10-0a4i-0900000000-62d73cc97ac426baf5d82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone n/a 10V, positive-QTOFsplash10-004l-9000000000-672e06fb3b7870b5e0662020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone n/a 10V, positive-QTOFsplash10-001i-9000000000-a5c95a778293e816e2982020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone n/a 10V, positive-QTOFsplash10-000t-9100000000-c3c9a32c71b3929313eb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Carvone n/a 10V, positive-QTOFsplash10-014i-9000000000-fb41d95361a6747c13942020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvone 10V, Positive-QTOFsplash10-0udi-0900000000-62861ac4cbf0b95e50692016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvone 20V, Positive-QTOFsplash10-0udi-5900000000-b282dcb5d4a98c3f852f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvone 40V, Positive-QTOFsplash10-1000-9100000000-0fd631d26260645c64ae2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvone 10V, Negative-QTOFsplash10-0002-0900000000-97d37f99bcaf0ed7d1082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvone 20V, Negative-QTOFsplash10-0002-0900000000-1817a8dceee7a31df4e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Carvone 40V, Negative-QTOFsplash10-001l-6900000000-581a45ee1ec95e2011382016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013718
KNApSAcK IDC00000807
Chemspider ID388655
KEGG Compound IDC01767
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439570
PDB IDNot Available
ChEBI ID15400
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1002741
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  2. Inglik N, Rudenko BA, Kakhnovskii IM, Koroleva TV: [Gas chromatographic study of the composition of the volatile components of the urine in normal subjects and patients with diabetes mellitus]. Lab Delo. 1989;(8):24-7. [PubMed:2477620 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. de Groot AC, Schmidt E: Essential Oils, Part III: Chemical Composition. Dermatitis. 2016 Jul-Aug;27(4):161-9. doi: 10.1097/DER.0000000000000193. [PubMed:27427817 ]
  8. Mahboubi M: Caraway as Important Medicinal Plants in Management of Diseases. Nat Prod Bioprospect. 2019 Jan;9(1):1-11. doi: 10.1007/s13659-018-0190-x. Epub 2018 Oct 29. [PubMed:30374904 ]
  9. Mollazadeh H, Afshari AR, Hosseinzadeh H: Review on the Potential Therapeutic Roles of Nigella sativa in the Treatment of Patients with Cancer: Involvement of Apoptosis: - Black cumin and cancer. J Pharmacopuncture. 2017 Sep;20(3):158-172. doi: 10.3831/KPI.2017.20.019. Epub 2017 Sep 30. [PubMed:30087792 ]
  10. Bahr TA, Rodriguez D, Beaumont C, Allred K: The Effects of Various Essential Oils on Epilepsy and Acute Seizure: A Systematic Review. Evid Based Complement Alternat Med. 2019 May 22;2019:6216745. doi: 10.1155/2019/6216745. eCollection 2019. [PubMed:31239862 ]
  11. Singh P, Pandey AK: Prospective of Essential Oils of the Genus Mentha as Biopesticides: A Review. Front Plant Sci. 2018 Sep 10;9:1295. doi: 10.3389/fpls.2018.01295. eCollection 2018. [PubMed:30250476 ]
  12. 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 ]
  13. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  14. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.