Vitamin E

Vitamin E Chemical Properties
Melting point 2.5-3.5 °C
Boiling point 200-220 °C0.1 mm Hg(lit.)
alpha 24 º (c=2, in isooctane 25 ºC)
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.
pka11.40±0.40(Predicted)
form oil
color clear yellow
Odorlt. yel. to red visc. oil, nearly odorless
Water Solubility INSOLUBLE
Merck 14,9495
BRN 4712525
Stability:Stable. Combustible. May be sensitive to light and air. Incompatible with strong oxidizing agents.
LogP10.962 (est)
CAS DataBase Reference59-02-9(CAS DataBase Reference)
NIST Chemistry ReferenceVitamin e(59-02-9)
EPA Substance Registry System2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)- (59-02-9)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 23-24/25-37/39-26
WGK Germany 1
RTECS DJ2900000
8-10-23
HS Code 29362800
Hazardous Substances Data59-02-9(Hazardous Substances Data)
Vitamin E Usage And Synthesis
Chemical Propertieslight yellow liquid
Chemical PropertiesVITAMIN E 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.
OriginatorDoppelherz,Queisser Pharma,Germany
Usesvitamin E, antioxidant
Usesα-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.
UsesUse in insect cell culture applications as an antioxidant.
DefinitionChEBI: 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.
Manufacturing ProcessManufacturing process for Vitamin E, 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 reaction is well known and has been practiced for many years (StallaBourdillon, Ind. Chim. Belg., 35, 13 (1970); "The Vitamins" Vol. 5, pages 168- 223, Academic Press, New York, 1967). The Synthesis of Vitamin E includes these steps as follows: Rearrangement to C15 Acetylene; Saponification of the C20 Dienol Acetate to Dehydrophytol;Condensation of Dehydrophytol with TMHQ to yield Dehydro-Vitamin E.
Therapeutic FunctionAntioxidant
General Descriptionα-Tocopherol is synthesized from γ-tocopherol by the action of enzyme γ-tocopherol methyltransferase. It is the major form of Vitamin E in human plasma. It is present in sunflower seed oil.
Health HazardThe physiological functions of vitamin E 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 vitamin E 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 Actionsα-Tocopherol is essential for the photosynthesis in Synechocystis sp. strain PCC 6803. Supplementation with α-Tocopherol decreases lipid peroxidation and platelet aggregation. It inhibits protein kinase C and may play key role in gene regulation.
Safety ProfileExperimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Purification MethodsVitamin E is a viscous yellow oil which is distilled at high vacuum. It has max at 294nm (E1cm 1% 71). It is oxygen and light sensitive and is best stored as its stable D--acetate [58-95-7] which is purified by evaporative distillation at b 180-200o(bath temperature)/0.7mm, and has [] D 25 +3.3o (c 5.1, EtOH). It forms needles at -30o and has m 26.5-27.5o, [] D 25 +0.25o (c 10, CHCl3). [NMR: Cohen et al. Helv Chim Acta 6 4 1158 1981, Burton & Ingold Acc Chem Res 1 9 194 1986, Karrer et al. Helv Chim Acta 2 1 520 1938, Robeson J Am Chem Soc, 64 1487 1942, 65 1660 1943.] Of the eight isomers the D--isomer is the most active. [See W. Friedrich “Vitamins” Walter de Guyter Publ, Berlin 1988.] [Beilstein 17/4 V 168.]
TOCORRETINATE Alkyl polyglucoside MULTIVITAMIN (±)-α-Tocopherol nicotinate DL-ALPHA-TOCOPHEROL HYDROGEN SUCCINATE 3-Bromoisonicotinic acid D-Α-TOCOPHEROL D-alpha-Tocopheryl acetate Petroleum sodium sulfonate alkyl phenyl polyoxyethylene ether ALPHA-TOCOPHEROL DL-ALPHA-TOCOPHEROL ACETATE Tocopherol (+/-)-ALPHA-TOCOPHEROL PHOSPHATE DISODIUM SALT DL-Α-TOCOPHEROL ACETATE Tocoretinate Natural vitamin E oil TOCOPHERYL LINOLEATE Vitamin E Oil Vitamine E

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