Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:52 UTC |
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Update date | 2020-09-17 15:30:23 UTC |
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Primary ID | FDB013718 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (R)-Carvone |
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Description | Carvone, 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). |
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CAS Number | 6485-40-1 |
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Structure | |
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Synonyms | Synonym | Source |
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(-)-(4R)-Carvone | ChEBI | (-)-(R)-Carvone | ChEBI | (-)-p-Mentha-6,8-dien-2-one | ChEBI | (4R)-Carvone | ChEBI | (5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one | ChEBI | (R)-(-)-Carvone | ChEBI | (R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one | ChEBI | (R)-5-Isopropenyl-2-methylcyclohex-2-en-1-one | ChEBI | L-1-Methyl-4-isopropenyl-6-cyclohexen-2-one | ChEBI | L-Carvone | ChEBI | L-p-Mentha-1(6),8-dien-2-one | ChEBI | Levo-carvone | ChEBI | (-)-Carvone | HMDB | (4R)-(-)-Carvone | HMDB | (R)-(-)-P-Mentha-6,8-dien-2-one | HMDB | 2-Methyl-5-(1-methylethenyl)-(R)-2-cyclohexen-1-one | HMDB | L(-)-Carvone | HMDB | (-)-(r)-carvone | biospider | (-)-carvone | biospider | (r)-carvone | biospider | 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)- | biospider | L-P-Mentha-1(6),8-dien-2-one | ChEBI | L(-)-carvone | biospider | p-Mentha-6,8-dien-2-one, (R)-(-)- | biospider |
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Predicted Properties | |
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Chemical Formula | C10H14O |
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IUPAC name | (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one |
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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 |
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InChI Key | ULDHMXUKGWMISQ-SECBINFHSA-N |
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Isomeric SMILES | CC(=C)[C@@H]1CC=C(C)C(=O)C1 |
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Average Molecular Weight | 150.2176 |
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Monoisotopic Molecular Weight | 150.10446507 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Monoterpenoids |
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Direct Parent | Menthane monoterpenoids |
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Alternative Parents | |
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Substituents | - P-menthane monoterpenoid
- Monocyclic monoterpenoid
- Cyclohexenone
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 79.96%; H 9.39%; O 10.65% | DFC |
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Melting Point | <15 oC | |
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Boiling Point | Bp 230-231° | DFC |
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Experimental Water Solubility | 1.31 mg/mL at 25 oC | SUZUKI,T (1991) |
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Experimental logP | 2.71 | GRIFFIN,S ET AL. (1999) |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]D -62.46 | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0f8c-9200000000-88f46d943b306bc533db | 2015-03-01 | View Spectrum | GC-MS | (R)-Carvone, non-derivatized, GC-MS Spectrum | splash10-0a59-9300000000-0663a3956cbefc28418a | Spectrum | GC-MS | (R)-Carvone, non-derivatized, GC-MS Spectrum | splash10-0a59-9300000000-0663a3956cbefc28418a | Spectrum | GC-MS | (R)-Carvone, non-derivatized, GC-MS Spectrum | splash10-0a59-9300000000-0663a3956cbefc28418a | Spectrum | GC-MS | (R)-Carvone, non-derivatized, GC-MS Spectrum | splash10-0a59-9300000000-0663a3956cbefc28418a | Spectrum | Predicted GC-MS | (R)-Carvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0f83-9200000000-e9569993e9ab3a8d9c56 | Spectrum | Predicted GC-MS | (R)-Carvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (R)-Carvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ , positive (Annotated) | splash10-052f-9600000000-9902205f6d338c08818d | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, positive | splash10-0udi-0900000000-52f6355f33c4b2243d8a | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, positive | splash10-0udi-0900000000-cb6bd893e3059c4e749a | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, positive | splash10-0udi-0900000000-12445f07d9581bb79ba9 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, positive | splash10-0zfr-0900000000-f9115bab64084ca3e9c6 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, positive | splash10-0zfr-0900000000-c2cc2f68aa635d48f7d2 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, positive | splash10-0pb9-0900000000-34673104b5cbea631cca | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, positive | splash10-0a4i-0900000000-3c5bc016004147d81ac1 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, positive | splash10-0a4i-0900000000-805c8d6f02a70e4d8ced | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, positive | splash10-0a4i-1900000000-90f1a3149285030d18d3 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 8V, positive | splash10-0a4i-4900000000-c900c93dbadd576b2e03 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 9V, positive | splash10-0a4l-9700000000-ccd0df21a8aba540288c | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 11V, positive | splash10-052f-9400000000-b05876718fef3d10e1e6 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 14V, positive | splash10-00kf-9200000000-97e06bb63f72b6a871e6 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 10V, positive | splash10-0a4i-0900000000-62d73cc97ac426baf5d8 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 10V, positive | splash10-004l-9000000000-672e06fb3b7870b5e066 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 10V, positive | splash10-001i-9000000000-a5c95a778293e816e298 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 10V, positive | splash10-000t-9100000000-c3c9a32c71b3929313eb | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 10V, positive | splash10-014i-9000000000-fb41d95361a6747c1394 | 2020-07-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0900000000-62861ac4cbf0b95e5069 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-5900000000-b282dcb5d4a98c3f852f | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-1000-9100000000-0fd631d26260645c64ae | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-97d37f99bcaf0ed7d108 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-1817a8dceee7a31df4e0 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001l-6900000000-581a45ee1ec95e201138 | 2016-08-03 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 388655 |
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ChEMBL ID | CHEMBL2229268 |
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KEGG Compound ID | C01767 |
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Pubchem Compound ID | 439570 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15400 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB35089 |
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CRC / DFC (Dictionary of Food Compounds) ID | JSX52-Q:JGG35-A |
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EAFUS ID | Not Available |
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Dr. Duke ID | (-)-CARVONE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000807 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 6485-40-1 |
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GoodScent ID | rw1002741 |
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SuperScent ID | 439570 |
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Wikipedia ID | Carvone |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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mint |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
| minty |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| sweet |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| spearmint |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| herbal |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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