Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2007-05-23 00:55:35 UTC |
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Update Date | 2022-03-07 02:49:31 UTC |
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HMDB ID | HMDB0006335 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | beta-Tocopherol |
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Description | beta-Tocopherol is an antioxidant which is synthesized by photosynthetic organisms and plays an important role in human and animal nutrition. beta-Tocopherols can be oxidized in dry CH2Cl2 or CH3CN by one electron to form cation radicals that deprotonate to form the neutral phenoxyl radicals, which are then immediately further oxidized by one electron to the phenoxonium cations (an ECE electrochemical mechanism, where E signifies an electron transfer and C represents a chemical step, with the electrochemical mechanism having been determined by in situ spectroscopic analysis). The phenoxonium cation of beta-tocopherol is stable for several minutes (PMID: 16771430 ). beta-Tocopherol has been identified in the human placenta (PMID: 32033212 ). |
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Structure | CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(O)=CC(C)=C2O1 InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1 |
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Synonyms | Value | Source |
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(2R)-2,5,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol | ChEBI | (2R)-3,4-Dihydro-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol | ChEBI | (2R,4'r,8'r)-beta-Tocopherol | ChEBI | (R,R,R)-beta-Tocopherol | ChEBI | 5,8-Dimethyltocol | ChEBI | RRR-beta-Tocopherol | ChEBI | (2R,4'r,8'r)-b-Tocopherol | Generator | (2R,4'r,8'r)-Β-tocopherol | Generator | (R,R,R)-b-Tocopherol | Generator | (R,R,R)-Β-tocopherol | Generator | RRR-b-Tocopherol | Generator | RRR-Β-tocopherol | Generator | b-Tocopherol | Generator | Β-tocopherol | Generator | beta Tocopherol | HMDB | 3,4-Dihydro-2,5,8-trimethyl-2-(4,8,12- trimethyltridecyl)-2H-1-benzopyran-6-ol | HMDB | b-Tocopherol skeleton | HMDB | Β-tocopherol skeleton | HMDB | Cumotocopherol | HMDB | DL-beta-Tocopherol | HMDB | DL-Β-tocopherol | HMDB | Neotocopherol | HMDB | p-Xylotocopherol | HMDB | beta-Tocopherol | MeSH | 2,5,8-Trimethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol | HMDB |
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Chemical Formula | C28H48O2 |
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Average Molecular Weight | 416.6795 |
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Monoisotopic Molecular Weight | 416.36543078 |
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IUPAC Name | (2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol |
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Traditional Name | β-tocopherol |
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CAS Registry Number | 148-03-8 |
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SMILES | CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(O)=CC(C)=C2O1 |
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InChI Identifier | InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1 |
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InChI Key | WGVKWNUPNGFDFJ-DQCZWYHMSA-N |
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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 | |
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Substituents | - Tocopherol
- Diterpenoid
- 1-benzopyran
- Benzopyran
- Chromane
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Benzenoid
- Oxacycle
- Organoheterocyclic compound
- Ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Biological locationSourceExogenousFoodAnimal originHerb and spiceVegetableFruitNutCereal and cereal productPulseGourdCoffee and coffee productSoyDishTeaBaking goodBeverageAquatic originMilk and milk productOther milk productFermented milk productFermented milkUnfermented milk- Milk (Cow) (FooDB: FOOD00618)
- Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
- Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
- Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
- Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)
Fat and oilEggBaby foodUnclassified food or beverageCocoa and cocoa productSnackConfectionery |
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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 | < 25 °C | 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 | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - beta-Tocopherol GC-MS (1 TMS) | splash10-00di-1490200000-f75de727e16d87c65fba | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - beta-Tocopherol GC-MS (Non-derivatized) | splash10-00di-1490200000-f75de727e16d87c65fba | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - beta-Tocopherol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0lyo-6954200000-ffcf92e6a6e2f34dd922 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - beta-Tocopherol GC-MS (1 TMS) - 70eV, Positive | splash10-00di-5644900000-b5341f1bdc151c1a796b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - beta-Tocopherol 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - beta-Tocopherol EI-EBEB (JMS-HX/HX 110A, JEOL) , Positive-QTOF | splash10-0gb9-3900600000-10f458ddcb7e7aa4df84 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - beta-Tocopherol n/a 29V, negative-QTOF | splash10-0f6t-0900600000-9a11a437c645252a72a5 | 2020-07-21 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Tocopherol 10V, Positive-QTOF | splash10-014i-0842900000-82c505b0548997aace83 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Tocopherol 20V, Positive-QTOF | splash10-0udi-1910000000-1b1a0fe2f352daa49e2c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Tocopherol 40V, Positive-QTOF | splash10-0pb9-4920000000-b63881a7743c06bdea15 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Tocopherol 10V, Negative-QTOF | splash10-014i-0100900000-2345f13b44d6c70d81e5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Tocopherol 20V, Negative-QTOF | splash10-014j-0912800000-4e68210f69fcd3f6c374 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Tocopherol 40V, Negative-QTOF | splash10-00kk-0914000000-f6f5255b874c4fc7f4f3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Tocopherol 10V, Negative-QTOF | splash10-014i-0000900000-a74b65a822c3cc7625b7 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Tocopherol 20V, Negative-QTOF | splash10-014i-0201900000-2dcdf4f502cc6e57342d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Tocopherol 40V, Negative-QTOF | splash10-024m-2913100000-fb9e3e53715df460db95 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Tocopherol 10V, Positive-QTOF | splash10-014i-3113900000-16d3b372ee248c26f313 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Tocopherol 20V, Positive-QTOF | splash10-0aor-9213100000-65be5213a11752835e85 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - beta-Tocopherol 40V, Positive-QTOF | splash10-052g-9400000000-947da441c6df0de93bed | 2021-09-25 | Wishart Lab | View Spectrum |
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Disease References | Colorectal cancer |
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- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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General References | - Wilson GJ, Lin CY, Webster RD: Significant differences in the electrochemical behavior of the alpha-, beta-, gamma-, and delta-tocopherols (vitamin E). J Phys Chem B. 2006 Jun 15;110(23):11540-8. [PubMed:16771430 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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