Alpha Tocopherol



Alpha tocopherol is a natural product. The PhEur 6.0 describes alpha-tocopherol as a clear, colorless or yellowish-brown, viscous, oily liquid.

Nonproprietary Names
  • BP: RRR-Alpha-Tocopherol
  • JP: Tocopherol
  • PhEur: RRR-a-Tocopherol
  • USP: Vitamin E
Antioxidant; therapeutic agent.



Synonyms

Copherol F1300; (+_)-3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12- trimethyltridecyl)-2H-1-benzopyran-6-ol; E307; RRR-a-tocopherolum; synthetic alpha tocopherol; all-rac-a-tocopherol; dl-a-tocopherol; 5,7,8-trimethyltocol.

Chemical Name and CAS Registry Number

(+_)- (2RS, 40RS, 80RS)-2, 5, 7, 8-Tetramethyl-2-(40, 80,120-trimethyltridecyl)-6-chromanol [10191-41-0]

Note that alpha tocopherol has three chiral centers, giving rise to eight isomeric forms. The naturally occurring form is known as dalpha tocopherol or (2R, 40R, 80R)-alpha-tocopherol. The synthetic form, dl-alpha tocopherol or simply alpha tocopherol, occurs as a racemic mixture containing equimolar quantities of all the isomers.
Similar considerations apply to beta, delta, and gamma tocopherol and tocopherol esters.

Empirical Formula and Molecular Weight
  • C29H50O2 430.72


Functional Category
  • Antioxidant; therapeutic agent.

Typical Properties
  • Boiling point 2358C
  • Density 0.947–0.951 g/cm3
  • Flash point 2408C
  • Ignition point 3408C
  • Refractive index n D 20 = 1.503–1.507
  • Solubility: Practically insoluble in water; freely soluble in acetone, ethanol, ether, and vegetable oils.

Method of Manufacture

Naturally occurring tocopherols are obtained by the extraction or molecular distillation of steam distillates of vegetable oils; for example, alpha tocopherol occurs in concentrations of 0.1–0.3% in corn, rapeseed, soybean, sunflower, and wheat germ oils. Beta and gamma tocopherol are usually found in natural sources along with alpha tocopherol. Racemic synthetic tocopherols may be prepared by the condensation of the appropriate methylated hydroquinone with racemic isophytol




Reference
https://www.cancer.gov/publications/dictionaries/cancer-terms/def/alpha-tocopherol
https://pubchem.ncbi.nlm.nih.gov/compound/alpha-Tocopherol
https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/alpha-tocopherol
https://www.drugbank.ca/drugs/DB14002
https://www.news-medical.net/health/Vitamin-E-ce91-Tocopherol.aspx
https://www.ahajournals.org/doi/10.1161/CIRCRESAHA.119.314944
https://med.libretexts.org/Bookshelves/Nutrition/Book%3A_Intermediate_Nutrition_(Lindshield)/09%3A_Antioxidant_Micronutrients/9.02%3A_Vitamin_E/9.2E%3A_Alpha-Tocopherol-_Natural_vs._Synthetic
https://academic.oup.com/carcin/article/27/11/2308/2391446

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