Record Information |
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Version | 1.0 |
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Created at | 2021-01-05 23:30:52 UTC |
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Updated at | 2021-08-19 23:59:52 UTC |
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NP-MRD ID | NP0014309 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | R-δ-tocotrienol |
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Provided By | NPAtlas |
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Description | Delta-Tocotrienol, also known as δ-tocotrienol or tocotrienol, delta, belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain. Thus, delta-tocotrienol is considered to be a quinone. Delta-Tocotrienol exists in all living organisms, ranging from bacteria to humans. Delta-Tocotrienol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. R-δ-tocotrienol is found in Bixa orellana, Cratoxylum cochinchinense, Cystophora monilifera, Garcinia kola, Kielmeyera coriacea, Kielmeyera lathrophyton, Kielmeyera reticulata and Sargassum siliquastrum. It was first documented in 2011 (PMID: 21598300). Based on a literature review a significant number of articles have been published on delta-Tocotrienol (PMID: 26093325) (PMID: 22816285) (PMID: 24486300) (PMID: 24294967). |
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Structure | [H]OC1=C([H])C(=C2O[C@](C([H])([H])[H])(C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C2=C1[H])C([H])([H])[H] InChI=1S/C27H40O2/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/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3/b21-12+,22-14+/t27-/m1/s1 |
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Synonyms | Value | Source |
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(2R)-2,8-Dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol | ChEBI | Δ-tocotrienol | Generator | Tocotrienol, delta | HMDB | (2R)-3,4-Dihydro-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-2H-1-benzopyran-6-ol | HMDB | (R)-delta-Tocotrienol | HMDB | (R)-Δ-tocotrienol | HMDB | 8-Methyltocotrienol | HMDB | D-delta-Tocotrienol | HMDB | D-Δ-tocotrienol | HMDB | delta-Tocotrienol | HMDB |
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Chemical Formula | C27H40O2 |
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Average Mass | 396.6150 Da |
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Monoisotopic Mass | 396.30283 Da |
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IUPAC Name | (2R)-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol |
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Traditional Name | delta tocotrienol |
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CAS Registry Number | Not Available |
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SMILES | CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1 |
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InChI Identifier | InChI=1S/C27H40O2/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/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3/b21-12+,22-14+/t27-/m1/s1 |
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InChI Key | ODADKLYLWWCHNB-LDYBVBFYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| 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 tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl 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 | Tocotrienols |
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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 | - Brkljaca R, Urban S: HPLC-NMR and HPLC-MS investigation of antimicrobial constituents in Cystophora monilifera and Cystophora subfarcinata. Phytochemistry. 2015 Sep;117:200-208. doi: 10.1016/j.phytochem.2015.06.014. Epub 2015 Jun 18. [PubMed:26093325 ]
- Ji X, Wang Z, Geamanu A, Sarkar FH, Gupta SV: Inhibition of cell growth and induction of apoptosis in non-small cell lung cancer cells by delta-tocotrienol is associated with notch-1 down-regulation. J Cell Biochem. 2011 Oct;112(10):2773-83. doi: 10.1002/jcb.23184. [PubMed:21598300 ]
- Asakawa Y, Ludwiczuk A, Harinantenaina L, Toyota M, Nishiki M, Bardon A, Nii K: Distribution of drimane sesquiterpenoids and tocopherols in liverworts, ferns and higher plants: Polygonaceae, Canellaceae and Winteraceae species. Nat Prod Commun. 2012 Jun;7(6):685-92. [PubMed:22816285 ]
- Singh VK, Wise SY, Scott JR, Romaine PL, Newman VL, Fatanmi OO: Radioprotective efficacy of delta-tocotrienol, a vitamin E isoform, is mediated through granulocyte colony-stimulating factor. Life Sci. 2014 Mar 11;98(2):113-22. doi: 10.1016/j.lfs.2014.01.065. Epub 2014 Jan 28. [PubMed:24486300 ]
- Li XH, Ghosh SP, Ha CT, Fu D, Elliott TB, Bolduc DL, Villa V, Whitnall MH, Landauer MR, Xiao M: Delta-tocotrienol protects mice from radiation-induced gastrointestinal injury. Radiat Res. 2013 Dec;180(6):649-57. doi: 10.1667/RR13398.1. Epub 2013 Dec 2. [PubMed:24294967 ]
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