Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-07-25 00:08:54 UTC |
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Update Date | 2021-09-14 15:19:52 UTC |
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HMDB ID | HMDB0012868 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 9'-Carboxy-gamma-chromanol |
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Description | 9'-Carboxy-gamma-tocopherol is a dehydrogenation carboxylate product of 9'-hydroxy-r-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. r-Tocopherol provides different antioxidant activities in food and in-vitro studies and showed higher activity in trapping lipophilic electrophiles and reactive nitrogen and oxygen species. From the metabolism end product, only that of r-tocopherol (2,7,8-trimethyl-2-(b-carboxyethyl)-6-hydroxychroman), but not that of a-tocopherol, was identified to provide natriuretic activity. Only the r-tocopherol plasma level served as biomarker for cancer and cardiovascular risk. |
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Structure | C[C@H](CCC[C@H](C)C(O)=O)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1 InChI=1S/C23H36O4/c1-15(8-6-10-16(2)22(25)26)9-7-12-23(5)13-11-19-14-20(24)17(3)18(4)21(19)27-23/h14-16,24H,6-13H2,1-5H3,(H,25,26)/t15-,16+,23-/m1/s1 |
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Synonyms | Value | Source |
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(2S,6R)-9-[(2R)-6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoate | HMDB | Γ-cdmohc | HMDB | gamma-CDMOHC | HMDB | γ-Carboxydimethyloctyl hydroxychroman | HMDB | γ-Carboxydimethyloctylhydroxychroman | HMDB | gamma-Carboxydimethyloctyl hydroxychroman | HMDB | gamma-Carboxydimethyloctylhydroxychroman | HMDB |
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Chemical Formula | C23H36O4 |
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Average Molecular Weight | 376.537 |
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Monoisotopic Molecular Weight | 376.261359639 |
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IUPAC Name | (2S,6R)-9-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid |
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Traditional Name | (2S,6R)-9-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnonanoic acid |
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CAS Registry Number | 1215088-64-4 |
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SMILES | C[C@H](CCC[C@H](C)C(O)=O)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1 |
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InChI Identifier | InChI=1S/C23H36O4/c1-15(8-6-10-16(2)22(25)26)9-7-12-23(5)13-11-19-14-20(24)17(3)18(4)21(19)27-23/h14-16,24H,6-13H2,1-5H3,(H,25,26)/t15-,16+,23-/m1/s1 |
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InChI Key | ODQOKHVJIYTOQE-VBURHUQHSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzopyrans |
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Sub Class | 1-benzopyrans |
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Direct Parent | 1-benzopyrans |
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Alternative Parents | |
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Substituents | - 1-benzopyran
- Medium-chain fatty acid
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Branched fatty acid
- Heterocyclic fatty acid
- Hydroxy fatty acid
- Methyl-branched fatty acid
- Fatty acyl
- Fatty acid
- Benzenoid
- Monocarboxylic acid or derivatives
- Oxacycle
- Ether
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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9'-Carboxy-gamma-chromanol,1TMS,isomer #1 | CC1=C(O)C=C2CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)C(=O)O[Si](C)(C)C)OC2=C1C | 2850.2 | Semi standard non polar | 33892256 | 9'-Carboxy-gamma-chromanol,1TMS,isomer #2 | CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)C(=O)O)OC2=C1C | 2921.7 | Semi standard non polar | 33892256 | 9'-Carboxy-gamma-chromanol,2TMS,isomer #1 | CC1=C(O[Si](C)(C)C)C=C2CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)C(=O)O[Si](C)(C)C)OC2=C1C | 2858.3 | Semi standard non polar | 33892256 | 9'-Carboxy-gamma-chromanol,1TBDMS,isomer #1 | CC1=C(O)C=C2CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C)OC2=C1C | 3115.5 | Semi standard non polar | 33892256 | 9'-Carboxy-gamma-chromanol,1TBDMS,isomer #2 | CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)C(=O)O)OC2=C1C | 3180.1 | Semi standard non polar | 33892256 | 9'-Carboxy-gamma-chromanol,2TBDMS,isomer #1 | CC1=C(O[Si](C)(C)C(C)(C)C)C=C2CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C)OC2=C1C | 3363.6 | Semi 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 - 9'-Carboxy-gamma-chromanol 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 - 9'-Carboxy-gamma-chromanol 10V, Positive-QTOF | splash10-0kdi-0419000000-cd057edae393743570b5 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-chromanol 20V, Positive-QTOF | splash10-0udi-0911000000-a634d5d40e9ad8466db6 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-chromanol 40V, Positive-QTOF | splash10-0udi-2900000000-567171c8ebdc774c19a0 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-chromanol 10V, Negative-QTOF | splash10-004i-0009000000-8be58d31ef5f29daf85c | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-chromanol 20V, Negative-QTOF | splash10-005a-0409000000-c4f9d5fd1cfb91f60b96 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-chromanol 40V, Negative-QTOF | splash10-05tb-7916000000-27664edfcab573c04ee2 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-chromanol 10V, Positive-QTOF | splash10-0ufr-1259000000-07af3dd22eab013841cd | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-chromanol 20V, Positive-QTOF | splash10-0012-1492000000-34cf07d467d81a9bf6a9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-chromanol 40V, Positive-QTOF | splash10-0fe3-4920000000-f1c204588a76056667ac | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-chromanol 10V, Negative-QTOF | splash10-004i-0009000000-8cfda78ea5a5ec24a352 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-chromanol 20V, Negative-QTOF | splash10-002b-0509000000-c1a7322cafcde235713d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9'-Carboxy-gamma-chromanol 40V, Negative-QTOF | splash10-02ou-1924000000-878d6d96351e5c61af97 | 2021-09-24 | Wishart Lab | View Spectrum |
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