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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 19:43:36 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004487
Secondary Accession Numbers
  • HMDB0061788
  • HMDB04487
  • HMDB61788
Metabolite Identification
Common Name(S)-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 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?1582752308
Synonyms
ValueSource
(+)-(4S)-CarvoneChEBI
(+)-(S)-CarvoneChEBI
(5S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(S)-(+)-CarvoneChEBI
(S)-(+)-p-Mentha-6,8-dien-2-oneChEBI
(S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(S)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-oneChEBI
(S)-5-Isopropenyl-2-methylcyclohex-2-en-1-oneChEBI
CarvolChEBI
CarvoneChEBI
D-(+)-CarvoneChEBI
D-CarvoneChEBI
(+)-CarvoneKegg
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneHMDB
D-p-Mentha-6,8(9)-dien-2-oneHMDB
(S)-CarvoneChEBI
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional Namecarvone, (+)-
CAS Registry Number2244-16-8
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-/m0/s1
InChI KeyULDHMXUKGWMISQ-VIFPVBQESA-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 Point231.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1300 mg/L at 18 °CNot Available
LogP1.267Not 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]+136.52831661259
DarkChem[M-H]-132.23931661259
DeepCCS[M+H]+138.49430932474
DeepCCS[M-H]-136.09830932474
DeepCCS[M-2H]-171.40330932474
DeepCCS[M+Na]+146.27530932474
AllCCS[M+H]+131.332859911
AllCCS[M+H-H2O]+126.732859911
AllCCS[M+NH4]+135.532859911
AllCCS[M+Na]+136.732859911
AllCCS[M-H]-134.732859911
AllCCS[M+Na-2H]-136.232859911
AllCCS[M+HCOO]-137.932859911

Predicted Kovats Retention Indices

Underivatized

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

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-Carvone,1TMS,isomer #1C=C(C)[C@@H]1C=C(O[Si](C)(C)C)C(C)=CC11385.2Semi standard non polar33892256
(S)-Carvone,1TMS,isomer #1C=C(C)[C@@H]1C=C(O[Si](C)(C)C)C(C)=CC11361.3Standard non polar33892256
(S)-Carvone,1TMS,isomer #1C=C(C)[C@@H]1C=C(O[Si](C)(C)C)C(C)=CC11648.9Standard polar33892256
(S)-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
(S)-Carvone,1TBDMS,isomer #1C=C(C)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC11537.6Standard non polar33892256
(S)-Carvone,1TBDMS,isomer #1C=C(C)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC11808.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (S)-Carvone EI-B (Non-derivatized)splash10-0a59-9200000000-b8485ca29dc163ef73862017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (S)-Carvone EI-B (Non-derivatized)splash10-0a59-9200000000-b8485ca29dc163ef73862018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (S)-Carvone EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418a2018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (S)-Carvone EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418a2018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (S)-Carvone EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418a2018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (S)-Carvone EI-B (Non-derivatized)splash10-0a59-9300000000-0663a3956cbefc28418a2018-05-25HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Carvone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8l-9200000000-0d07518eb09c4d6d75122016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Carvone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Carvone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0kai-9200000000-87c2472a96aad69404af2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Carvone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0pb9-0900000000-cad4b73ca0349a0fca732012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Carvone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4l-9700000000-4f8b99aefc0ccf7e31f42012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Carvone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-052f-9600000000-9902205f6d338c08818d2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Carvone EI-B (JEOL JMS-D-300) , Positive-QTOFsplash10-0a59-9200000000-b8485ca29dc163ef73862012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Carvone 20V, Negative-QTOFsplash10-0a59-9300000000-4251d272babda4de5c362021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Carvone 40V, Negative-QTOFsplash10-014i-5900000000-424a2cd188d1d2f5213d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Carvone 10V, Negative-QTOFsplash10-0002-2900000000-8101d73f0cfb2435bca72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Carvone 20V, Positive-QTOFsplash10-0aou-9200000000-f171ea0515bba0d8369d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Carvone 10V, Positive-QTOFsplash10-0udj-9500000000-9859933bdc05bac9d6632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Carvone 40V, Positive-QTOFsplash10-00ou-9100000000-935629946779efc8b4ff2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Carvone 10V, Positive-QTOFsplash10-0udi-0900000000-62861ac4cbf0b95e50692016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Carvone 20V, Positive-QTOFsplash10-0udi-5900000000-b282dcb5d4a98c3f852f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Carvone 40V, Positive-QTOFsplash10-1000-9100000000-0fd631d26260645c64ae2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Carvone 10V, Negative-QTOFsplash10-0002-0900000000-97d37f99bcaf0ed7d1082016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Carvone 20V, Negative-QTOFsplash10-0002-0900000000-1817a8dceee7a31df4e02016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Carvone 40V, Negative-QTOFsplash10-001l-6900000000-581a45ee1ec95e2011382016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Carvone 10V, Positive-QTOFsplash10-0a4i-3900000000-f279f95a33eb225c1b142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Carvone 20V, Positive-QTOFsplash10-07eg-9400000000-34f0a30acb50659192b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Carvone 40V, Positive-QTOFsplash10-00mo-9000000000-7b658cbdc17dd03f44ed2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Carvone 10V, Negative-QTOFsplash10-0002-0900000000-22917433edc8ad9dbc2e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Carvone 20V, Negative-QTOFsplash10-0002-0900000000-c0270d719fd67ba328d92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Carvone 40V, Negative-QTOFsplash10-001j-9700000000-dfa5cb40b478707933162021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013718
KNApSAcK IDC00010891
Chemspider ID15855
KEGG Compound IDC11383
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16724
PDB IDNot Available
ChEBI ID15399
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1007121
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. Hahn I, Scherer PW, Mozell MM: A mass transport model of olfaction. J Theor Biol. 1994 Mar 21;167(2):115-28. [PubMed:8207942 ]
  3. Jager W, Mayer M, Reznicek G, Buchbauer G: Percutaneous absorption of the montoterperne carvone: implication of stereoselective metabolism on blood levels. J Pharm Pharmacol. 2001 May;53(5):637-42. [PubMed:11370703 ]
  4. 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 ]
  5. McHugh D, Hu SS, Rimmerman N, Juknat A, Vogel Z, Walker JM, Bradshaw HB: N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, the putative abnormal cannabidiol receptor. BMC Neurosci. 2010 Mar 26;11:44. doi: 10.1186/1471-2202-11-44. [PubMed:20346144 ]
  6. Tauber S, Paulsen K, Wolf S, Synwoldt P, Pahl A, Schneider-Stock R, Ullrich O: Regulation of MMP-9 by a WIN-binding site in the monocyte-macrophage system independent from cannabinoid receptors. PLoS One. 2012;7(11):e48272. doi: 10.1371/journal.pone.0048272. Epub 2012 Nov 6. [PubMed:23139770 ]
  7. Bondarenko AI, Drachuk K, Panasiuk O, Sagach V, Deak AT, Malli R, Graier WF: N-Arachidonoyl glycine suppresses Na(+)/Ca(2)(+) exchanger-mediated Ca(2)(+) entry into endothelial cells and activates BK(Ca) channels independently of GPCRs. Br J Pharmacol. 2013 Jun;169(4):933-48. doi: 10.1111/bph.12180. [PubMed:23517055 ]
  8. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.