CHEBI:47771 - β-tocopherol

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ChEBI Name β-tocopherol
ChEBI ID CHEBI:47771
ChEBI ASCII Name beta-tocopherol
Definition A tocopherol in which the chroman-6-ol core is substituted by methyl groups at positions 5 and 8. While it is found in low concentrations in many vegetable oils, only cottonseed oil contains significant amounts.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:35069, CHEBI:22855
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Formula C28H48O2
Net Charge 0
Average Mass 416.67952
Monoisotopic Mass 416.36543
InChI 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
InChIKey WGVKWNUPNGFDFJ-DQCZWYHMSA-N
SMILES CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCc2c(C)c(O)cc(C)c2O1
Metabolite of Species Details
Quercus rubra (NCBI:txid3512) See: DOI
Quercus robur (NCBI:txid38942) See: DOI
Panax ginseng (NCBI:txid4054) From MetaboLights See: MetaboLights Study
Helianthus annuus (NCBI:txid4232) Found in seed (PO:0009010). See: DOI
Homo sapiens (NCBI:txid9606) See: DOI
Homo sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
(via vitamin E )
(via tocol )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
food component
A physiological role played by any substance that is distributed in foodstuffs. It includes materials derived from plants or animals, such as vitamins or minerals, as well as environmental contaminants.
fat-soluble vitamin (role)
Any vitamin that dissolves in fats and are stored in body tissues. Unlike the water-soluble vitamins, they are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess.
(via vitamin E )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing β-tocopherol (CHEBI:47771) has role food component (CHEBI:78295)
β-tocopherol (CHEBI:47771) has role plant metabolite (CHEBI:76924)
β-tocopherol (CHEBI:47771) is a tocopherol (CHEBI:27013)
β-tocopherol (CHEBI:47771) is a vitamin E (CHEBI:33234)
IUPAC Name
(2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol
Synonyms Sources
(2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol IUPAC
(2R)-3,4-dihydro-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol ChemIDplus
(2R,4'R,8'R)-β-tocopherol ChEBI
(R,R,R)-β-tocopherol ChEBI
5,8-dimethyltocol ChEBI
beta-Tocopherol KEGG COMPOUND
β-tocopherol UniProt
RRR-β-tocopherol ChEBI
Manual Xrefs Databases
5256784 ChemSpider
Beta-Tocopherol Wikipedia
BETA-TOCOPHEROL MetaCyc
C00007364 KNApSAcK
C14152 KEGG COMPOUND
ES2232276 Patent
FDB012381 FooDB
HMDB0006335 HMDB
LMPR02020059 LIPID MAPS
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Registry Numbers Types Sources
148-03-8 CAS Registry Number KEGG COMPOUND
16698-35-4 CAS Registry Number ChemIDplus
93070 Beilstein Registry Number Beilstein
93070 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11390183 PubMed citation Europe PMC
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9920007 PubMed citation Europe PMC
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IND606272494 Agricola citation Europe PMC
IND607266641 Agricola citation Europe PMC
PMC7258573 PubMed Central citation Europe PMC
Last Modified
04 August 2021