Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:32 UTC |
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Update date | 2020-09-17 15:30:29 UTC |
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Primary ID | FDB014916 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (1S,4S)-Dihydrocarvone |
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Description | Dihydrocarvone, 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-eritritol-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 ( http://www.thegoodscentscompany.com/data/rw1031221.html#toorgano). 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. |
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CAS Number | 6909-25-7 |
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Structure | |
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Synonyms | Synonym | Source |
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Not Available | Not Available |
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Predicted Properties | |
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Chemical Formula | C10H16O |
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IUPAC name | (2S,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one |
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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 |
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InChI Key | AZOCECCLWFDTAP-IUCAKERBSA-N |
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Isomeric SMILES | C[C@H]1CC[C@@H](CC1=O)C(C)=C |
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Average Molecular Weight | 152.2334 |
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Monoisotopic Molecular Weight | 152.120115134 |
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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
- 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 | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 78.90%; H 10.59%; O 10.51% | DFC |
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Melting Point | Not Available | |
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Boiling Point | Bp 220-221° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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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 -19 | 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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Predicted GC-MS | (1S,4S)-Dihydrocarvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00m3-9100000000-fa9716dc62a7dad68748 | Spectrum | Predicted GC-MS | (1S,4S)-Dihydrocarvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (1S,4S)-Dihydrocarvone, 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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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-1900000000-8861ba576d835c24c4e2 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0zfr-9700000000-7b7dfb5b5671e2efed19 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-100r-9000000000-02b93dd813cef6744911 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-3bdcde43911faafba8b7 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0900000000-66279fba8a75e05ec84b | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05n3-9500000000-02a124dc8509d82c4bb8 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0gws-7900000000-b08efab8959a09a26216 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000x-9200000000-13ccbe770389182b9c06 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-4b6afc70d0efd7f97f15 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-c373c9eea3cebf186f53 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-1900000000-6d20364e296745592a69 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kn-6900000000-23186e60d8ffad674527 | 2021-09-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 391455 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C11415 |
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Pubchem Compound ID | 443183 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 168 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB36080 |
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CRC / DFC (Dictionary of Food Compounds) ID | JXJ77-S:JXJ80-O |
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EAFUS ID | Not Available |
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Dr. Duke ID | (-)-DIHYDROCARVONE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00010947 |
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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 | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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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 | Not Available |
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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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