Quick Search
α-Tocopherol (alpha-tocopherol) is synthesized from γ-tocopherol by the action of enzyme γ-tocopherol methyltransferase.
α-Tocopherol (alpha-tocopherol) is the major form of Vitamin E in human plasma.
α-Tocopherol (alpha-tocopherol) is present in sunflower seed oil.
CAS: 59-02-9
MF: C29H50O2
MW: 430.71
EINECS: 200-412-2
α-Tocopherol (alpha-tocopherol) that has R,R,R configuration.
The naturally occurring stereoisomer of α-Tocopherol (alpha-tocopherol), it is found particularly in sunflower and olive oils.
α-Tocopherol (alpha-tocopherol) is a type of vitamin E.
α-Tocopherol (alpha-tocopherol)'s E number is "E307".
α-Tocopherol (alpha-tocopherol) 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 which allows for penetration into biological membranes.
Compared to the others, α-Tocopherol (alpha-tocopherol) is preferentially absorbed and accumulated in humans.
α-Tocopherol (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, α-Tocopherol (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 α-Tocopherol (alpha-tocopherol) homeostasis in a variety of oxidative stress-related disease conditions in humans."
One of these disease conditions is the α-Tocopherol (alpha-tocopherol) role in the use by malaria parasites to protect themselves from the highly oxidative environment in erythrocytes.
α-Tocopherol (alpha-tocopherol) is a potent antioxidant and the most biologically active form of vitamin E.
Because α-Tocopherol (alpha-tocopherol) is the form of vitamin E most essential to biological functioning, α-Tocopherol (alpha-tocopherol) is often used synonymously with vitamin E.
α-Tocopherol (alpha-tocopherol) is the form of vitamin E that is preferentially absorbed and accumulated in humans.
The measurement of "vitamin E" activity in international units (IU) was based on fertility enhancement by the prevention of miscarriages in pregnant rats relative to α-tocopherol.
Although the mono-methylated form ddd-γ-tocopherol is the most prevalent form of vitamin E in oils, there is evidence that rats can methylate this form to the preferred α-Tocopherol (alpha-tocopherol), since several generations of rats retained α-Tocopherol (alpha-tocopherol) tissue levels, even when those generations were fed only γ-tocopherol through their lives.
There are three stereocenters in α-Tocopherol (alpha-tocopherol), so this is a chiral molecule.
The eight stereoisomers of α-Tocopherol (alpha-tocopherol) differ in the arrangement of groups around these stereocenters.
In the image of α-Tocopherol (alpha-tocopherol) below, all three stereocenters are in the R form.
However, if the middle of the three stereocenters were changed (so the hydrogen was now pointing down and the methyl group pointing up), this would become the structure of α-Tocopherol (alpha-tocopherol).
These stereoisomers also may be named in an alternative older nomenclature, where the stereocenters are either in the d or l form.
α-Tocopherol (alpha-tocopherol) is a type of vitamin E which is accumulated and absorbed in humans.
α-Tocopherol (alpha-tocopherol) has an E number, E307, and is used as an antioxidant.
Ungraded products supplied are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use.
α-Tocopherol (alpha-tocopherol) is a brownish red or transparent light yellow oily liquid with a mild, special odor and taste.
Soluble in ethanol, acetone, ether, chloroform or vegetable oil, almost insoluble in water.
High boiling point (250 ° C), stable to heat.
α-Tocopherol (alpha-tocopherol) becomes dark red when exposed to air and light.
α-Tocopherol (alpha-tocopherol) has no heat and does not participate in human metabolism.
α-Tocopherol (alpha-tocopherol) is widely found in plants and animals in nature, and can be extracted from a variety of plant oils, leafy vegetables, animal organs and substances relatively rich in α-Tocopherol (alpha-tocopherol) and Tocotrienols are extracted.
At present, α-Tocopherol (alpha-tocopherol) mainly comes from vegetable oils and their products.
α-Tocopherol (alpha-tocopherol) is the orally bioavailable alpha form of the naturally-occurring fat-soluble vitamin E, with potent antioxidant and cytoprotective activities.
Upon administration, α-Tocopherol (alpha-tocopherol) neutralizes free radicals, thereby protecting tissues and organs from oxidative damage.
α-Tocopherol (alpha-tocopherol) gets incorporated into biological membranes, prevents protein oxidation and inhibits lipid peroxidation, thereby maintaining cell membrane integrity and protecting the cell against damage.
In addition, α-Tocopherol (alpha-tocopherol) inhibits the activity of protein kinase C (PKC) and PKC-mediated pathways.
α-Tocopherol (alpha-tocopherol) also modulates the expression of various genes, plays a key role in neurological function, inhibits platelet aggregation and enhances vasodilation.
Compared with other forms of tocopherol, α-Tocopherol (alpha-tocopherol) is the most biologically active form and is the form that is preferentially absorbed and retained in the body.
α-Tocopherol (alpha-tocopherol) is a naturally-occurring form of vitamin E, a fat-soluble vitamin with potent antioxidant properties.
Considered essential for the stabilization of biological membranes (especially those with high amounts of polyunsaturated fatty acids), α-Tocopherol (alpha-tocopherol) is a potent peroxyl radical scavenger and inhibits noncompetitively cyclooxygenase activity in many tissues, resulting in a decrease in prostaglandin production.
α-Tocopherol (alpha-tocopherol) also inhibits angiogenesis and tumor dormancy through suppressing vascular endothelial growth factor (VEGF) gene transcription.
α-Tocopherol (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.
pka: 11.40±0.40(Predicted)
Form: oil
Color: clear yellow
Water Solubility: INSOLUBLE
Merck: 14,9495
BRN: 4712525
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: α-Tocopherol (alpha-tocopherol) (59-02-9)
EPA Substance Registry System: α-Tocopherol (alpha-tocopherol) (2R)- (59-02-9)
α-Tocopherol (alpha-tocopherol) is sometimes referred to as the antisterility vitamin, factor X (an earlier designation), chemically vitamin E is alphatocopherol.
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.
Light green yellow or light yellow viscous liquid, basically tasteless, the relative density of 0.947~0.955.
Insoluble in water, but soluble in ethanol, gasoline, ethyl esters and vegetable oils.
α-Tocopherol (alpha-tocopherol) is stable to heat and almost does not decompose when heated to 200 ℃; α-Tocopherol (alpha-tocopherol) is stable to oxygen in air, but α-Tocopherol (alpha-tocopherol) undergoes slow oxidation, and the oxidation resistance of the synthesized product is weaker than that of the natural product.
The color of the visible light gradually darkened.
Physiological Function and Role
α-Tocopherol (alpha-tocopherol) including α, β, δ, gamma tocopherol and the corresponding tocotrienols and other 8 kinds of substances, belonging to the fat-soluble vitamins, with anti-free radicals, anti-aging, prevention of skin keratinization, improve human and animal physical immune function and cellular immune function, prevention and treatment of cardiovascular and cerebrovascular diseases and other important physiological functions.
α-Tocopherol (alpha-tocopherol) has two major sources of natural vitamin E and synthetic VE.
Natural α-Tocopherol (alpha-tocopherol) is a mixed tocopherol containing a variety of monomers, but α-Tocopherol (alpha-tocopherol) is superior to synthetic α-Tocopherol (alpha-tocopherol) in both physiological activity and antioxidant capacity, and natural α-Tocopherol (alpha-tocopherol) on the human body non-toxic side effects, so in food, nutrition and health products and cosmetics and other industries, α-Tocopherol (alpha-tocopherol) by the majority of consumers of all ages.
Stereoisomers
α-Tocopherol (alpha-tocopherol)l has three stereocenters, so it is a chiral molecule.
The eight stereoisomers of α-Tocopherol (alpha-tocopherol) differ in the configuration of these stereocenters.
RRR-α-tocopherol is the natural one.
The older name of RRR-α-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 tocopherol is defined as 2⁄3 milligram of RRR-α-tocopherol (formerly named d-α-tocopherol).
1 IU 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.
Uses
α-Tocopherol (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.
α-Tocopherol (alpha-tocopherol) use in insect cell culture applications as an antioxidant.
α-Tocopherol (alpha-tocopherol) is used for the Prevention of abortion, habitual abortion and threatened abortion caused by vitamin E deficiency, and also for the treatment of infertility and infant nutritional giant cell anemia.
α-Tocopherol (alpha-tocopherol) is used in the following products: pharmaceuticals and cosmetics and personal care products.
α-Tocopherol (alpha-tocopherol) is used in the following areas: health services.
Release to the environment of α-Tocopherol (alpha-tocopherol) can occur from industrial use: in processing aids at industrial sites and of substances in closed systems with minimal release.
α-Tocopherol (alpha-tocopherol) is used in the following products: cosmetics and personal care products and pharmaceuticals.
Other release to the environment of α-Tocopherol (alpha-tocopherol) is likely to occur from: indoor use as processing aid.
α-Tocopherol (alpha-tocopherol) has a strong reduction, in the human body metabolism in the process of antioxidant and thus prevent the role of aging, can maintain the normal function of reproductive organs.
α-Tocopherol (alpha-tocopherol) may also be used as a nutrient enhancer.
China's provisions can be used to strengthen sesame oil, salad oil, margarine and dairy products.
The dosage was 100 ~ 180mg/kg, the dosage was 40 ~ 70ug/kg in fortified infant food, and the maximum dosage was 20~40mg/L in fortified tocopherol beverage; the amount used in the fortified milk drink is 10-20ug/kg.
α-Tocopherol (alpha-tocopherol) is widely distributed in animal and vegetable fats, egg yolk, milk, fruit, lettuce leaves and other foods.
Wheat germ oil, corn oil, peanut oil and cottonseed oil are also rich in α-Tocopherol (alpha-tocopherol).
Health Hazard
The physiological functions of α-Tocopherol (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 α-Tocopherol (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.
Biochem/physiol Actions
α-Tocopherol (alpha-tocopherol) is essential for the photosynthesis in Synechocystis sp. strain PCC 6803.
Supplementation with α-Tocopherol (alpha-tocopherol) decreases lipid peroxidation and platelet aggregation.
α-Tocopherol (alpha-tocopherol) inhibits protein kinase C and may play key role in gene regulation.
Synonyms
VITAMIN E
alpha-Tocopherol
D-alpha-Tocopherol
59-02-9
5,7,8-Trimethyltocol
(+)-alpha-Tocopherol
2074-53-5
Aquasol E
TOCOPHEROL
(R,R,R)-alpha-Tocopherol
Phytogermine
Eprolin
a-Tocopherol
(2R,4'R,8'R)-alpha-Tocopherol
dl-a-Tocopherol
Denamone
Viteolin
Esorb
alpha-Tocopherol, D-
Tocopherol alpha
alpha-Vitamin E
alpha Tocopherol
D-alpha tocopherol
(2R)-2,5,7,8-TETRAMETHYL-2-[(4R,8R)-4,8,12-TRIMETHYLTRIDECYL]CHROMAN-6-OL
(R)-2,5,7,8-Tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-ol
Vitamin Ea
Syntopherol
Tocopherol (R,S)
1406-18-4
CHEBI:18145
Vitamin-E
Evitaminum
Profecundin
Waynecomycin
Almefrol
Emipherol
Epsilan
Etamican
Tokopharm
Vascuals
Vitayonon
Etavit
Ilitia
Evion
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
BPBio1_000362
18920-62-2
Vitaplex E
DTXSID0026339
Eprolin S
Spavit E
ido-E
Endo E
N9PR3490H9
Vita E
Lan-E
Med-E
Antisterility vitamin
a-Vitamin E
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-
Vi-E
E307
(+/-)-alpha-Tocopherol
2,5,7,8-Tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanol
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-rel-
DTXCID706339
Viprimol
alpha-Tokoferol
d-a-tocopherol
MFCD00072045
rel-alpha-Vitamin E
RRR-alpha-tocopherol
Vitamin E alpha
Viterra E
E Prolin
CAS-59-02-9
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*)]]-
SMR000471844
VIV
alpha-Tocopherol acid
Tenox GT 1
Rhenogran Ronotec 50
Covitol F 1000
3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
E 307 (tocopherol)
(all-R)-alpha-Tocopherol
Phytogermin
Palmvtee
alpha-Tocoferol
(+-)-Med-E
UNII-N9PR3490H9
Vitamin Ealpha
CCRIS 3588
NSC-20812
a-D-Tocopherol
.ALPHA.-TOCOPHEROL, D-
HSDB 2556Pheryl-E
DL--Tocopherol
Vita plus E
rel--Vitamin E
d-..-Tocopherol
Vitamin e d-alpha
NCGC00016688-02
(+)--tocopherol
Prestwick_653
EINECS 200-412-2
EINECS 215-798-8
EINECS 218-197-9
.alpha.-Vitamin E
(+)-a-Tocopherol
NSC 20812
NSC 82623
RRR-alpha-tocopheryl
Vitamin E [USP]
()-alpha-Tocopherol
delta-alpha-tocopherol
alpha-delta-Tocopherol
Tocopherol, d-alpha-
Vitamin E (D-form)
CHEMBL47
(R,R,R)-a-Tocopherol
Prestwick3_000404
E 307
(+)- alpha -Tocopherol
(+)-.alpha.-Tocopherol
bmse000600
R,r,r-.alpha.-tocopherol
EC 200-412-2
SCHEMBL3097
UNII-H4N855PNZ1
BIDD:PXR0174
BSPBio_000328
MLS001066396
MLS001335981
MLS001335982
BIDD:ER0562
INS NO.307A
T1539_SIGMA
H4N855PNZ1
INS-307A
(+)-ALPHA-TOCOPHEROL-
ALPHA-TOCOPHEROL [HSDB]
(2R,4'R,8'R)-a-Tocopherol
.ALPHA.-TOCOPHEROL [MI]
(+)--Tocopherol; D--Tocopherol
HMS2096A10
HMS2231G08
C29H50O2 (D-alpha-tocopherol)
D-ALPHA TOCOPHEROL [MART.]
HY-N0683
ZINC4095858
Tox21_110563
Tox21_113208
Tox21_202081
BDBM50458513
E-307A
LMPR02020001
AKOS004910417
CS-8161
DB00163
(2R)-2-((4R,8R)-4,8,12-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol
NCGC00142625-01
NCGC00142625-04
NCGC00142625-05
NCGC00142625-06
NCGC00142625-07
NCGC00142625-10
NCGC00259630-01
(2R*(4R*,8R*))-(1)-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
AS-13990
J24.260H
rel-(+)--Tocopherol; rel-D--Tocopherol
T2309
C02477
F82497
d-alpha, d-beta, d-gamma & d-delta tocopherols
EN300-7417123
Q158348
Q-201932
W-107596
W-109164
Z2235811339
07AA93F0-3339-4EEC-B50B-ADB70F657087
(2R,4'R,8'R)-2,5,7,8-Tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanol
3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1- -benzopyran-6-ol
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
(2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol
(R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromen-6-ol
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*))-(+-)-
