Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:40:25 UTC |
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Updated at | 2021-08-19 23:59:23 UTC |
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NP-MRD ID | NP0002786 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | delta-Tocopherol |
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Provided By | BMRB |
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Description | Delta-Tocopherol, also known as RRR-δ-tocopherol or 8-methyltocol, belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. Thus, delta-tocopherol is considered to be a quinone. Delta-Tocopherol exists in all living organisms, ranging from bacteria to humans. Delta-Tocopherol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. delta-Tocopherol is found in Calendula officinalis, Campanula medium, Carum carvi L. , Caryodendron orinocense, Cocos nucifera L. , Crataegus monogyna, Guarea kunthiana, Schefflera taiwaniana, Hippophae rhamnoides, Hypericum ericoides, Juglans regia L. , Linum usitatissimum, Muntingia calabura, Olea europaea, Origanum vulgare, Psophocarpus tetragonolobus, Radula marginata, Radula perrottetii, Rubus idaeus, Salvia rosmarinus, Secale cereale L. , Sesamum indicum, Jungermannia infusca, Spinacia oleracea, Potamogeton pectinatus, Torreya nucifera and Vaccinium macrocarpon Aiton . It was first documented in 1999 (PMID: 10385606). Based on a literature review a significant number of articles have been published on delta-Tocopherol (PMID: 17984079) (PMID: 14695946) (PMID: 16400056) (PMID: 12600864). |
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Structure | CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1 InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1 |
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Synonyms | Value | Source |
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(+)-delta-Tocopherol | ChEBI | (2R)-2,8-Dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol | ChEBI | (2R)-3,4-Dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol | ChEBI | (2R,4'r,8'r)-delta-Tocopherol | ChEBI | (R,R,R)-delta-Tocopherol | ChEBI | 8-Methyltocol | ChEBI | e309 | ChEBI | RRR-delta-Tocopherol | ChEBI | (+)-Δ-tocopherol | Generator | (2R,4'r,8'r)-Δ-tocopherol | Generator | (R,R,R)-Δ-tocopherol | Generator | RRR-Δ-tocopherol | Generator | Δ-tocopherol | Generator | Vitamine e | HMDB | (2R,4’R,8’R)-δ-Tocopherol | HMDB | d-delta-Tocopherol | HMDB | d-δ-Tocopherol | HMDB | delta-D-Tocopherol | HMDB | delta-Tocopherol | HMDB | delta-Vitamin E | HMDB | δ-D-Tocopherol | HMDB | δ-Vitamin E | HMDB |
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Chemical Formula | C27H46O2 |
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Average Mass | 402.6529 Da |
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Monoisotopic Mass | 402.34978 Da |
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IUPAC Name | (2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol |
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Traditional Name | delta tocopherol |
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CAS Registry Number | Not Available |
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SMILES | CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1 |
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InChI Identifier | InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1 |
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InChI Key | GZIFEOYASATJEH-VHFRWLAGSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. |
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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 | Quinone and hydroquinone lipids |
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Direct Parent | Tocopherols |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Passi S, De Pita O, Grandinetti M, Simotti C, Littarru GP: The combined use of oral and topical lipophilic antioxidants increases their levels both in sebum and stratum corneum. Biofactors. 2003;18(1-4):289-97. doi: 10.1002/biof.5520180233. [PubMed:14695946 ]
- Clarke MW, Ward NC, Wu JH, Hodgson JM, Puddey IB, Croft KD: Supplementation with mixed tocopherols increases serum and blood cell gamma-tocopherol but does not alter biomarkers of platelet activation in subjects with type 2 diabetes. Am J Clin Nutr. 2006 Jan;83(1):95-102. doi: 10.1093/ajcn/83.1.95. [PubMed:16400056 ]
- Brigelius-Flohe R, Traber MG: Vitamin E: function and metabolism. FASEB J. 1999 Jul;13(10):1145-55. [PubMed:10385606 ]
- Liu M, Wallmon A, Olsson-Mortlock C, Wallin R, Saldeen T: Mixed tocopherols inhibit platelet aggregation in humans: potential mechanisms. Am J Clin Nutr. 2003 Mar;77(3):700-6. doi: 10.1093/ajcn/77.3.700. [PubMed:12600864 ]
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