ALPHA-TOCOPHEROL

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. 

CAS:    59-02-9
MF:    C29H50O2
MW:    430.71
EINECS:    200-412-2

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.
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: 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.

Uses    
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    
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. 

Health Hazard    
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.

Biochem/physiol Actions    
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.

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 2556
Pheryl-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*))-(+-)-