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 20:54:37 UTC |
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Update Date | 2022-03-07 02:54:40 UTC |
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HMDB ID | HMDB0035869 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | alpha-Rotunol |
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Description | alpha-Rotunol, also known as a-rotunol, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Based on a literature review a small amount of articles have been published on alpha-Rotunol. |
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Structure | CC(=C)C1CCC2(C)CC(=O)C=C(C)C2(O)C1 InChI=1S/C15H22O2/c1-10(2)12-5-6-14(4)9-13(16)7-11(3)15(14,17)8-12/h7,12,17H,1,5-6,8-9H2,2-4H3 |
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Synonyms | Value | Source |
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a-Rotunol | Generator | Α-rotunol | Generator | [4AS-(4aalpha,6beta,8abeta)]-4a,5,6,7,8,8a-hexahydro-4a-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)-2(1H)-naphthalenone | HMDB | b-Rotunol | Generator | Β-rotunol | Generator |
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Chemical Formula | C15H22O2 |
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Average Molecular Weight | 234.334 |
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Monoisotopic Molecular Weight | 234.161979948 |
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IUPAC Name | 4a-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one |
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Traditional Name | 4a-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)-5,6,7,8-tetrahydro-1H-naphthalen-2-one |
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CAS Registry Number | 24405-56-9 |
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SMILES | CC(=C)C1CCC2(C)CC(=O)C=C(C)C2(O)C1 |
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InChI Identifier | InChI=1S/C15H22O2/c1-10(2)12-5-6-14(4)9-13(16)7-11(3)15(14,17)8-12/h7,12,17H,1,5-6,8-9H2,2-4H3 |
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InChI Key | WDFLKCAWQQMJCA-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. |
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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 | Sesquiterpenoids |
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Direct Parent | Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
- Cyclohexenone
- Tertiary alcohol
- Cyclic alcohol
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 87.5 - 88.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 121.1 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | Not Available | Not Available |
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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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alpha-Rotunol,1TMS,isomer #1 | C=C(C)C1CCC2(C)CC(=O)C=C(C)C2(O[Si](C)(C)C)C1 | 2028.3 | Semi standard non polar | 33892256 | alpha-Rotunol,1TMS,isomer #2 | C=C(C)C1CCC2(C)C=C(O[Si](C)(C)C)C=C(C)C2(O)C1 | 1987.2 | Semi standard non polar | 33892256 | alpha-Rotunol,2TMS,isomer #1 | C=C(C)C1CCC2(C)C=C(O[Si](C)(C)C)C=C(C)C2(O[Si](C)(C)C)C1 | 1950.4 | Semi standard non polar | 33892256 | alpha-Rotunol,2TMS,isomer #1 | C=C(C)C1CCC2(C)C=C(O[Si](C)(C)C)C=C(C)C2(O[Si](C)(C)C)C1 | 1958.8 | Standard non polar | 33892256 | alpha-Rotunol,1TBDMS,isomer #1 | C=C(C)C1CCC2(C)CC(=O)C=C(C)C2(O[Si](C)(C)C(C)(C)C)C1 | 2273.4 | Semi standard non polar | 33892256 | alpha-Rotunol,1TBDMS,isomer #2 | C=C(C)C1CCC2(C)C=C(O[Si](C)(C)C(C)(C)C)C=C(C)C2(O)C1 | 2217.9 | Semi standard non polar | 33892256 | alpha-Rotunol,2TBDMS,isomer #1 | C=C(C)C1CCC2(C)C=C(O[Si](C)(C)C(C)(C)C)C=C(C)C2(O[Si](C)(C)C(C)(C)C)C1 | 2406.1 | Semi standard non polar | 33892256 | alpha-Rotunol,2TBDMS,isomer #1 | C=C(C)C1CCC2(C)C=C(O[Si](C)(C)C(C)(C)C)C=C(C)C2(O[Si](C)(C)C(C)(C)C)C1 | 2415.2 | 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 - alpha-Rotunol GC-MS (Non-derivatized) - 70eV, Positive | splash10-015d-9520000000-7f204ce9c3a9ca728c82 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Rotunol GC-MS (1 TMS) - 70eV, Positive | splash10-006x-6090000000-51946f21782ce8c1dfd3 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Rotunol 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 - alpha-Rotunol 10V, Negative-QTOF | splash10-001i-0090000000-462acfe4e44a2d558f81 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Rotunol 20V, Negative-QTOF | splash10-001i-0090000000-196f7d26364442dc650d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Rotunol 40V, Negative-QTOF | splash10-0gb9-3960000000-c98bf03080f51e9baf45 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Rotunol 10V, Negative-QTOF | splash10-001i-0090000000-9087f47ed0ae51229a17 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Rotunol 20V, Negative-QTOF | splash10-001i-0090000000-096295cb81e359e18667 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Rotunol 40V, Negative-QTOF | splash10-0fs9-2910000000-a1829c2a73845cf311ef | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Rotunol 10V, Positive-QTOF | splash10-014r-0290000000-fdf8209b97f5396811e1 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Rotunol 20V, Positive-QTOF | splash10-014i-5690000000-af1926a67454fbc887ab | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Rotunol 40V, Positive-QTOF | splash10-0uxv-9310000000-294cb7d800d088fb2605 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Rotunol 10V, Positive-QTOF | splash10-004i-0920000000-3fa5e82ae57b9c864daf | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Rotunol 20V, Positive-QTOF | splash10-0gdi-3920000000-4f68e880120bd4526cde | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Rotunol 40V, Positive-QTOF | splash10-05ql-9800000000-c616a56b3168e3bc97a8 | 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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