Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-11 21:08:58 UTC |
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Update Date | 2023-02-21 17:25:03 UTC |
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HMDB ID | HMDB0036080 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (1S,4S)-Dihydrocarvone |
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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. |
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Structure | C[C@H]1CC[C@@H](CC1=O)C(C)=C 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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Synonyms | Value | Source |
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(2S,5S)-2-Methyl-5-isopropenylcyclohexanone | ChEBI | (2S,5S)-5-Isopropenyl-2-methylcyclohexanone | ChEBI | (-)-Dihydrocarvone | HMDB | (-)-trans-Dihydrocarvone | HMDB | 1S,4S-Dihydrocarvone | HMDB |
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Chemical Formula | C10H16O |
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Average Molecular Weight | 152.2334 |
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Monoisotopic Molecular Weight | 152.120115134 |
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IUPAC Name | (2S,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one |
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Traditional Name | (-)-dihydrocarvone |
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CAS Registry Number | 6909-25-7 |
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SMILES | C[C@H]1CC[C@@H](CC1=O)C(C)=C |
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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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Chemical Taxonomy |
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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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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(1S,4S)-Dihydrocarvone,1TMS,isomer #1 | C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C)C1 | 1368.3 | Semi standard non polar | 33892256 | (1S,4S)-Dihydrocarvone,1TMS,isomer #1 | C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C)C1 | 1353.2 | Standard non polar | 33892256 | (1S,4S)-Dihydrocarvone,1TMS,isomer #2 | C=C(C)[C@@H]1C=C(O[Si](C)(C)C)[C@@H](C)CC1 | 1305.4 | Semi standard non polar | 33892256 | (1S,4S)-Dihydrocarvone,1TMS,isomer #2 | C=C(C)[C@@H]1C=C(O[Si](C)(C)C)[C@@H](C)CC1 | 1353.4 | Standard non polar | 33892256 | (1S,4S)-Dihydrocarvone,1TBDMS,isomer #1 | C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1 | 1603.3 | Semi standard non polar | 33892256 | (1S,4S)-Dihydrocarvone,1TBDMS,isomer #1 | C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1 | 1528.8 | Standard non polar | 33892256 | (1S,4S)-Dihydrocarvone,1TBDMS,isomer #2 | C=C(C)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C)CC1 | 1540.5 | Semi standard non polar | 33892256 | (1S,4S)-Dihydrocarvone,1TBDMS,isomer #2 | C=C(C)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C)CC1 | 1504.4 | Standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - (1S,4S)-Dihydrocarvone GC-MS (Non-derivatized) - 70eV, Positive | splash10-00m3-9100000000-fa9716dc62a7dad68748 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (1S,4S)-Dihydrocarvone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (1S,4S)-Dihydrocarvone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 10V, Positive-QTOF | splash10-0udi-1900000000-8861ba576d835c24c4e2 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 20V, Positive-QTOF | splash10-0zfr-9700000000-7b7dfb5b5671e2efed19 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 40V, Positive-QTOF | splash10-100r-9000000000-02b93dd813cef6744911 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 10V, Negative-QTOF | splash10-0udi-0900000000-3bdcde43911faafba8b7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 20V, Negative-QTOF | splash10-0udi-0900000000-66279fba8a75e05ec84b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 40V, Negative-QTOF | splash10-05n3-9500000000-02a124dc8509d82c4bb8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 10V, Positive-QTOF | splash10-0gws-7900000000-b08efab8959a09a26216 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 20V, Positive-QTOF | splash10-000x-9200000000-13ccbe770389182b9c06 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 40V, Positive-QTOF | splash10-0006-9000000000-4b6afc70d0efd7f97f15 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 10V, Negative-QTOF | splash10-0udi-0900000000-c373c9eea3cebf186f53 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 20V, Negative-QTOF | splash10-0udi-1900000000-6d20364e296745592a69 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1S,4S)-Dihydrocarvone 40V, Negative-QTOF | splash10-00kn-6900000000-23186e60d8ffad674527 | 2021-09-25 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB014916 |
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KNApSAcK ID | C00010947 |
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Chemspider ID | 391455 |
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KEGG Compound ID | C11415 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 443183 |
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PDB ID | Not Available |
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ChEBI ID | 168 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1054071 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- 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 ]
- 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 ]
- 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 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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