Alpha-tocopherol is a type of vitamin E.
Alpha-tocopherol's E number is "E307".
All feature a chromane ring, with a hydroxyl group that can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain which allows for penetration into biological membranes.
Alpha-tocopherol exists in eight different forms, four tocopherols and four tocotrienols.
Compared to the others, Alpha-tocopherol is preferentially absorbed and accumulated in humans.
Alpha-tocopherol is found in a variety of tissues, being lipid-soluble, and taken up by the body in a wide variety of ways.
The most prevalent form, Alpha-tocopherol, is involved in molecular, cellular, biochemical processes closely related to overall lipoprotein and lipid homeostasis.
Ongoing research is believed to be "critical for manipulation of Alpha-tocopherol homeostasis in a variety of oxidative stress-related disease conditions in humans."
One of these disease conditions is the Alpha-tocopherol role in the use by malaria parasites to protect themselves from the highly oxidative environment in erythrocytes.
Alpha-tocopherol has three stereocenters, so it is a chiral molecule.
The eight stereoisomers of Alpha-tocopherol differ in the configuration of these stereocenters.
Alpha-tocopherol is the natural one.
The older name of Alpha-tocopherol is d-α-tocopherol, but this d/l naming should no longer be used, because whether l-α-tocopherol should mean SSS enantiomer or the SRR diastereomer is not clear, from historical reasons.
The SRR may be named 2-epi-α-tocopherol, the diastereomeric mixture of RRR-α-tocopherol and 2-epi-α-tocopherol may be called 2-ambo-α-tocopherol (formerly named dl-α-tocopherol).
The mixture of all eight diastereomers is called all-rac-α-tocopherol.
One IU of Alpha-tocopherol is defined as 2⁄3 milligram of RRR-α-tocopherol (formerly named d-α-tocopherol).
Alpha-tocopherol is also defined as 0.9 mg of an equal mix of the eight stereoisomers, which is a racemic mixture, all-rac-α-tocopheryl acetate.
This mix of stereoisomers is often called dl-α-tocopheryl acetate.
Starting with May 2016, the IU unit is made obsolete, such that 1 mg of "Vitamin E" is 1 mg of d-alpha-tocopherol or 2 mg of dl-alpha-tocopherol.
An Alpha-tocopherol that has R,R,R configuration.
The naturally occurring stereoisomer of Alpha-tocopherol, it is found particularly in sunflower and olive oils.
Alpha-tocopherol is synthesized from γ-tocopherol by the action of enzyme γ-tocopherol methyltransferase.
Alpha-tocopherol is the major form of Vitamin E in human plasma.
Alpha-tocopherol is present in sunflower seed oil.
A nutrient that the body needs in small amounts to stay healthy and work the way Alpha-tocopherol should.
Alpha-tocopherol is fat-soluble (can dissolve in fats and oils) and is found in seeds, nuts, leafy green vegetables, and vegetable oils.
Alpha-tocopherol boosts the immune system and helps keep blood clots from forming.
Alpha-tocopherol also helps prevent cell damage caused by free radicals (highly reactive chemicals).
Alpha-tocopherol is being studied in the prevention and treatment of some types of cancer.
Alpha-tocopherol is a type of antioxidant.
Also called Alpha-tocopherol.
Alpha-tocopherol is used as a dietary supplement when the amount of Alpha-tocopherol taken in the diet is not enough.
People most at risk for Alpha-tocopherol deficiency are those with a limited variety of food in their diet and people with Crohn's disease (a condition in which the body attacks the lining of the digestive tract, causing pain, diarrhea, weight loss, and fever), cystic fibrosis (an inborn disease that causes problems with breathing, digestion, and reproduction), or who have gastrointestinal (GI) malabsorption problems (problems absorbing food).
Alpha-tocopherol is also used to treat vitamin E deficiency in those at risk due to certain diseases and conditions.
Alpha-tocopherol is in a class of medications called antioxidants.
Alpha-tocopherol is needed by the body to support the immune system and for blood clotting.
Alpha-tocopherol works as an antioxidant to protect your cells against free radicals.
Alpha-tocopherol is the primary form of vitamin E that is preferentially used by the human body to meet appropriate dietary requirements.
In particular, the RRR-alpha-tocopherol (or sometimes called the d-alpha-tocopherol stereoisomer) stereoisomer is considered the natural formation of Alpha-tocopherol and generally exhibits the greatest bioavailability out of all of the alpha-tocopherol stereoisomers.
Moreover, RRR-alpha-tocopherol acetate is a relatively stabilized form of Alpha-tocopherol that is most commonly used as a food additive when needed 6.
Alpha-tocopherol is subsequently most commonly indicated for dietary supplementation in individuals who may demonstrate a genuine deficiency in Alpha-tocopherol.
Alpha-tocopherol itself is naturally found in various foods, added to others, or used in commercially available products as a dietary supplement.
Nevertheless, Alpha-tocopherol is known to be a fat-soluble antioxidant that has the capability to neutralize endogenous free radicals.
This biologic action of Alpha-tocopherol consequently continues to generate ongoing interest and study in whether or not its antioxidant abilities may be used to help assist in preventing or treating a number of different conditions like cardiovascular disease, ocular conditions, diabetes, cancer and more.
At the moment however, there exists a lack of formal data and evidence to support any such additional indications for Alpha-tocopherol use.
Alpha-tocopherol is an antioxidant, Alpha-tocopherol helps to protect cells, tissues, and organs from damaging effects caused by ‘free radicals’, which are responsible for the aging process and can lead to various health conditions such as heart disease, cancer, and inflammatory conditions.
Alpha-tocopherol helps to prevent arteries from clogging by blocking the conversion of cholesterol into plaque that sticks to blood vessel walls.
Numerous clinical studies have reported that a higher intake of Alpha-tocopherol from food and dietary supplementation is associated with a lower risk of heart disease and other types of cardiovascular disease.
Studies have shown that Alpha-tocopherol may help protect against cataracts and age-related macular degeneration because of its antioxidant effects.
Alpha-tocopherol Chemical Properties
Melting point: 2.5-3.5 °C
Alpha: 24 º (c=2, in isooctane 25 ºC)
Boiling point: 200-220 °C0.1 mm Hg(lit.)
Density: 0.95 g/mL at 25 °C(lit.)
Refractive index: n20/D 1.505(lit.)
Fp: 253 °C
Storage temp.: -20°C
Solubility: Practically insoluble in water, freely soluble in acetone, in anhydrous ethanol, in methylene chloride and in fatty oils.
Color: clear yellow
Water Solubility: INSOLUBLE
Stability: Stable. Combustible. May be sensitive to light and air. Incompatible with strong oxidizing agents.
CAS DataBase Reference: 59-02-9(CAS DataBase Reference)
NIST Chemistry Reference: Alpha-tocopherol (59-02-9)
EPA Substance Registry System: Alpha-tocopherol (59-02-9)
Alpha-tocopherol is sometimes referred to as the antisterility vitamin, factor X (an earlier designation), chemically vitamin E is Alpha-tocopherol.
Active analogues and related compounds include: dl-α-Tocopherol; 1-α-tocopherol; esters (succinate, acetate, phosphate), and β, ζ 1, ζ 2- tocopherols.
The principal physiological forms are D-a-tocopherol, tocopheronolactone, and their phosphate esters.
Alpha-tocopherol is the most bioactive of the naturally occurring forms of Vitamin E.
Richest sources are green vegetables, grains, and oils, particularly palm, safflower and sunflower oils.
Alpha-tocopherol use in insect cell culture applications as an antioxidant.
Manufacturing process for Alpha-tocopherol, that is, α-tocopherol (5,7,8-trimethyltocol) in the past has been accomplished primarily by reacting trimethylhydroquinone (TMHQ) with isophytol (3,7,11,15-tetramethylhexadec-1-en-3-ol) or phytol (3,7,11,15-tetramethylhexadec-2-en-1-ol) in a condensation reaction.
The physiological functions of Alpha-tocopherol substances include:
(1) bio logical antioxidant;
(2) normal growth maintenance;
(3) protects unsaturated fatty acids and membrane structures;
(4) aids intestinal absorption of unsaturated fatty acids;
(5) maintains normal muscle metabolism;
(6) maintains integrity of vascular system and central nervous system;
(7) detoxifying agent; and
(8) maintains kidney tubules, lungs, genital structures, liver, and red blood cell membranes.
In livestock and laboratory animals, a deficiency of Alpha-tocopherol substances may cause degeneration of reproductive tissues, muscular dystrophy, encephalomalacia, and liver necrosis.
Considerable research is required to fully determine supplementation of livestock diets unless typical symptoms of a deficiency appear.
Symptoms have appeared where there are selenium deficiencies in the soil and where there are excessive levels of nitrates in the soil.
“White muscle” is the term used to describe a condition of muscular dystrophy in cattle.
Alpha-tocopherol is essential for the photosynthesis in Synechocystis sp. strain PCC 6803.
Supplementation with Alpha-tocopherol decreases lipid peroxidation and platelet aggregation.
Alpha-tocopherol inhibits protein kinase C and may play key role in gene regulation.
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-rel-
Vitamin E alpha
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-, (2R)-
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, (2R-(2R*(4R*,8R*)))-
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, [2R-[2R*(4R*,8R*)]]-
Tenox GT 1
Rhenogran Ronotec 50
Covitol F 1000
E 307 (tocopherol)
Vita plus E
Vitamin e d-alpha
Vitamin E [USP]
Vitamin E (D-form)
(+)- alpha -Tocopherol
D-ALPHA TOCOPHEROL [MART.]
d-alpha, d-beta, d-gamma & d-delta tocopherols
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, 2R- 2R*(4R*,8R*) -
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, (2R*(4R*,8R*))-(+-)-