Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2017-09-08 16:53:25 UTC |
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Update Date | 2022-03-07 03:18:07 UTC |
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HMDB ID | HMDB0112262 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | gamma-Carotene |
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Description | gamma-Carotene is a cyclic carotene obtained by the cyclization of lycopene. It is found in human serum and breast milk (PMID: 9164160 ). Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds, and crustacea. Animals are unable to synthesize carotenoids de novo and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer-preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important (PMID: 1416048 , 15003396 ). |
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Structure | CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C InChI=1S/C40H56/c1-32(2)18-13-21-35(5)24-15-26-36(6)25-14-22-33(3)19-11-12-20-34(4)23-16-27-37(7)29-30-39-38(8)28-17-31-40(39,9)10/h11-12,14-16,18-20,22-27,29-30H,13,17,21,28,31H2,1-10H3/b12-11+,22-14+,23-16+,26-15+,30-29+,33-19+,34-20+,35-24+,36-25+,37-27+ |
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Synonyms | Value | Source |
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g-Carotene | Generator | γ-Carotene | Generator | gamma-Carotene | HMDB | all-trans-gamma-Carotene | HMDB | all-trans-γ-Carotene | HMDB |
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Chemical Formula | C40H56 |
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Average Molecular Weight | 536.888 |
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Monoisotopic Molecular Weight | 536.438201803 |
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IUPAC Name | 2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaen-1-yl]-1,3,3-trimethylcyclohex-1-ene |
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Traditional Name | gamma-carotene |
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CAS Registry Number | 472-93-5 |
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SMILES | CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C |
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InChI Identifier | InChI=1S/C40H56/c1-32(2)18-13-21-35(5)24-15-26-36(6)25-14-22-33(3)19-11-12-20-34(4)23-16-27-37(7)29-30-39-38(8)28-17-31-40(39,9)10/h11-12,14-16,18-20,22-27,29-30H,13,17,21,28,31H2,1-10H3/b12-11+,22-14+,23-16+,26-15+,30-29+,33-19+,34-20+,35-24+,36-25+,37-27+ |
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InChI Key | HRQKOYFGHJYEFS-BXOLYSJBSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. |
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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 | Tetraterpenoids |
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Direct Parent | Carotenes |
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Alternative Parents | |
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Substituents | - Carotene
- Branched unsaturated hydrocarbon
- Cycloalkene
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- 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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Not Available | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | 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 IndicesUnderivatized |
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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 - gamma-Carotene GC-MS (Non-derivatized) - 70eV, Positive | splash10-00xr-6011690000-65457434be9838207569 | 2017-11-06 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - gamma-Carotene LC-ESI-QTOF 20V, positive-QTOF | splash10-0109-0951010000-2fc07b3278bb21c7ae84 | 2020-07-21 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - gamma-Carotene 10V, Positive-QTOF | splash10-000j-0339780000-e5bd060050db05cdabc3 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - gamma-Carotene 20V, Positive-QTOF | splash10-000t-0229300000-e04971ffd91f8586b02b | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - gamma-Carotene 40V, Positive-QTOF | splash10-00lb-2129500000-c1110517c942830471bc | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - gamma-Carotene 10V, Negative-QTOF | splash10-000i-0000090000-2dd5f27bb4b48f77f692 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - gamma-Carotene 20V, Negative-QTOF | splash10-000i-0001190000-c8267995f58f48f021e4 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - gamma-Carotene 40V, Negative-QTOF | splash10-014i-0239460000-8ca9ae88c16638dbcff7 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - gamma-Carotene 10V, Negative-QTOF | splash10-000i-0111090000-d0e7266c0c6b3f4a8307 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - gamma-Carotene 20V, Negative-QTOF | splash10-000j-0956240000-71afb100961fc10a23b7 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - gamma-Carotene 40V, Negative-QTOF | splash10-0udj-1508910000-320bf87c3d21b8d26955 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - gamma-Carotene 10V, Positive-QTOF | splash10-000i-2049650000-b215fe5b83f148c4d2ff | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - gamma-Carotene 20V, Positive-QTOF | splash10-003r-7123900000-dce47fa2bea9a264c209 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - gamma-Carotene 40V, Positive-QTOF | splash10-0wn9-6617910000-4d6ce7381cde3060909f | 2021-09-24 | Wishart Lab | View Spectrum |
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General References | - Khachik F, Beecher GR, Goli MB, Lusby WR, Smith JC Jr: Separation and identification of carotenoids and their oxidation products in the extracts of human plasma. Anal Chem. 1992 Sep 15;64(18):2111-22. [PubMed:1416048 ]
- Fraser PD, Bramley PM: The biosynthesis and nutritional uses of carotenoids. Prog Lipid Res. 2004 May;43(3):228-65. [PubMed:15003396 ]
- Khachik F, Spangler CJ, Smith JC Jr, Canfield LM, Steck A, Pfander H: Identification, quantification, and relative concentrations of carotenoids and their metabolites in human milk and serum. Anal Chem. 1997 May 15;69(10):1873-81. [PubMed:9164160 ]
- 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 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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