CHEBI:22470 - α-tocopherol

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name α-tocopherol
ChEBI ID CHEBI:22470
ChEBI ASCII Name alpha-tocopherol
Definition A tocopherol that is chroman-6-ol substituted by methyl groups at positions 2, 5, 7 and 8 and a 4,8,12-trimethyltridecyl group at position 2.
Stars This entity has been manually annotated by the ChEBI Team.
Wikipedia License
α-Tocopherol (alpha-tocopherol) is a type of vitamin E. Its E number is "E307". Vitamin E exists in eight different forms, four tocopherols and four tocotrienols. All feature a chromane ring, with a hydroxyl group that can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain, along with an aromatic ring is situated near the carbonyls in the fatty acyl chains of the phospholipid bilayer, allows for penetration into biological membranes. It is found most in the membrane's non-raft domains, associated with omega-3 and 6 fatty acids, to partially prevent oxidation. The most prevalent form, α-tocopherol, is involved in molecular, cellular, biochemical processes closely related to overall lipoprotein and lipid homeostasis. Compared to the others, α-tocopherol is preferentially absorbed and accumulated in humans. Vitamin E is found in a variety of tissues, being lipid-soluble, and taken up by the body in a wide variety of ways. Ongoing research is believed to be "critical for manipulation of vitamin E homeostasis in a variety of oxidative stress-related disease conditions in humans." One of these disease conditions is the α-tocopherol role in the use by malaria parasites to protect themselves from the highly oxidative environment in erythrocytes. A second of these disease conditions is the α-tocopherol antioxidant properties' role cardiovascular heart disease. In preventing LDL (low-density lipoprotein) oxidation, it is able to decrease chances of atherosclerosis and arterial build-up.
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Formula C29H50O2
Net Charge 0
Average Mass 430.707
Monoisotopic Mass 430.38108
Roles Classification
Chemical Role(s): food antioxidant
An antioxidant that used as a food additives to help guard against food deterioration.
antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
(via tocol )
(via vitamin E )
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 antioxidant
An antioxidant that used as a food additives to help guard against food deterioration.
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 )
Application(s): food antioxidant
An antioxidant that used as a food additives to help guard against food deterioration.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing α-tocopherol (CHEBI:22470) has role food antioxidant (CHEBI:77962)
α-tocopherol (CHEBI:22470) has role plant metabolite (CHEBI:76924)
α-tocopherol (CHEBI:22470) is a tocopherol (CHEBI:27013)
α-tocopherol (CHEBI:22470) is a vitamin E (CHEBI:33234)
Incoming (R,R,R)-α-tocopherol (CHEBI:18145) is a α-tocopherol (CHEBI:22470)
(R,R,S)-α-tocopherol (CHEBI:177081) is a α-tocopherol (CHEBI:22470)
(R,S,R)-α-tocopherol (CHEBI:177084) is a α-tocopherol (CHEBI:22470)
(R,S,S)-α-tocopherol (CHEBI:177085) is a α-tocopherol (CHEBI:22470)
(S,R,R)-α-tocopherol (CHEBI:177086) is a α-tocopherol (CHEBI:22470)
(S,R,S)-α-tocopherol (CHEBI:177090) is a α-tocopherol (CHEBI:22470)
(S,S,R)-α-tocopherol (CHEBI:177089) is a α-tocopherol (CHEBI:22470)
(S,S,S)-α-tocopherol (CHEBI:46430) is a α-tocopherol (CHEBI:22470)
IUPAC Name
rel-(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol
Synonyms Sources
(±)-alpha-tocopherol ChEBI
(±)-α-tocopherol ChemIDplus
2,5,7,8-tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanol ChemIDplus
all-rac-α-tocopherol ChEBI
dl-α-tocopherol ChemIDplus
E 307 ChEBI
E-307 ChEBI
E307 ChEBI
Manual Xrefs Databases
Alpha-Tocopherol Wikipedia
D02332 KEGG DRUG
View more database links
Registry Numbers Types Sources
10191-41-0 CAS Registry Number ChemIDplus
8176170 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
23949732 PubMed citation Europe PMC
24683365 PubMed citation Europe PMC
Last Modified
31 May 2023
General Comment
2021-08-04 Please note: The totally synthetic vitamin E, obtained without any control of stereochemistry, is a mixture in unspecified proportions of four racemates or pairs of enantiomers (i.e. eight diastereoisomers). It should be called all-rac-α-tocopherol (it was formerly known as dl-α-tocopherol, although this designation was previously used for 2-ambo-α-tocopherol).