Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 20:48:21 UTC |
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Update Date | 2022-03-07 02:54:37 UTC |
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HMDB ID | HMDB0035783 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (+)-Menthone |
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Description | (+)-Menthone, also known as (1S,4R)-menthone, 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. Based on a literature review a small amount of articles have been published on (+)-Menthone. |
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Structure | [H][C@]1(C)CC[C@]([H])(C(C)C)C(=O)C1 InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m0/s1 |
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Synonyms | Value | Source |
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(1S,4R)-Menthone | ChEBI | (1S,4R)-p-Menthan-3-one | ChEBI | (2R,5S)-2-Isopropyl-5-methylcyclohexanone | ChEBI | (+)-(1S,4R)-Menthone | HMDB | (2R,5S)-5-Methyl-2-(propan-2-yl)cyclohexanone | HMDB | Menthone | MeSH, HMDB | (+)-Menthone | HMDB | (2R,5S)-5-Methyl-2-(1-methylethyl)cyclohexanone | HMDB | D-Menthone | HMDB |
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Chemical Formula | C10H18O |
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Average Molecular Weight | 154.2493 |
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Monoisotopic Molecular Weight | 154.135765198 |
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IUPAC Name | (2R,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-one |
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Traditional Name | (+)-menthone |
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CAS Registry Number | 3391-87-5 |
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SMILES | CC(C)[C@H]1CC[C@H](C)CC1=O |
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InChI Identifier | InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m0/s1 |
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InChI Key | NFLGAXVYCFJBMK-DTWKUNHWSA-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 | |
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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 | |
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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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(+)-Menthone,1TMS,isomer #1 | CC(C)C1=C(O[Si](C)(C)C)C[C@@H](C)CC1 | 1342.3 | Semi standard non polar | 33892256 | (+)-Menthone,1TMS,isomer #1 | CC(C)C1=C(O[Si](C)(C)C)C[C@@H](C)CC1 | 1360.6 | Standard non polar | 33892256 | (+)-Menthone,1TMS,isomer #2 | CC(C)[C@H]1CC[C@H](C)C=C1O[Si](C)(C)C | 1290.0 | Semi standard non polar | 33892256 | (+)-Menthone,1TMS,isomer #2 | CC(C)[C@H]1CC[C@H](C)C=C1O[Si](C)(C)C | 1346.5 | Standard non polar | 33892256 | (+)-Menthone,1TBDMS,isomer #1 | CC(C)C1=C(O[Si](C)(C)C(C)(C)C)C[C@@H](C)CC1 | 1565.8 | Semi standard non polar | 33892256 | (+)-Menthone,1TBDMS,isomer #1 | CC(C)C1=C(O[Si](C)(C)C(C)(C)C)C[C@@H](C)CC1 | 1544.0 | Standard non polar | 33892256 | (+)-Menthone,1TBDMS,isomer #2 | CC(C)[C@H]1CC[C@H](C)C=C1O[Si](C)(C)C(C)(C)C | 1493.2 | Semi standard non polar | 33892256 | (+)-Menthone,1TBDMS,isomer #2 | CC(C)[C@H]1CC[C@H](C)C=C1O[Si](C)(C)C(C)(C)C | 1503.7 | Standard non polar | 33892256 |
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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 - (+)-Menthone GC-MS (Non-derivatized) - 70eV, Positive | splash10-06r7-9300000000-1d150f2cf0a23dbfef0b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (+)-Menthone 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 - (+)-Menthone 10V, Positive-QTOF | splash10-0a4i-0900000000-fa99f8c083212e4f2fc3 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (+)-Menthone 20V, Positive-QTOF | splash10-0bt9-9800000000-7bf975ea31bcef83aa61 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (+)-Menthone 40V, Positive-QTOF | splash10-0aor-9000000000-3f8923896797c4486693 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (+)-Menthone 10V, Negative-QTOF | splash10-0udi-0900000000-d55afdef2faae68197a6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (+)-Menthone 20V, Negative-QTOF | splash10-0udi-0900000000-91ec697d11dad181a342 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (+)-Menthone 40V, Negative-QTOF | splash10-01oy-9600000000-7933610ac6051fc8ef81 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (+)-Menthone 10V, Negative-QTOF | splash10-0udi-0900000000-d2363ae8d4dbdcccda80 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (+)-Menthone 20V, Negative-QTOF | splash10-0udi-0900000000-084e13e285859f435a61 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (+)-Menthone 40V, Negative-QTOF | splash10-0gbc-9700000000-57929498deae48afce7a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (+)-Menthone 10V, Positive-QTOF | splash10-0bti-3900000000-5b9ac9ca9aaff729e2d1 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (+)-Menthone 20V, Positive-QTOF | splash10-0532-9200000000-ac0243da1ad4aa3d859e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (+)-Menthone 40V, Positive-QTOF | splash10-0006-9000000000-d3a7bbb5abb9a0381a39 | 2021-09-22 | Wishart Lab | View Spectrum |
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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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