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rac-alpha-Tocopherol

CATALOG # 1072

Specifications

  • Catalog #:1072
  • Scientific Name:rac-alpha-Tocopherol
  • Common Name:5,7,8-Trimethyltocol
  • Empirical Formula:C29H50O2
  • CAS#10191-41-0
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:431
  • Unit:50 mg/ml, 1ml
  • Solvent:hexane
  • Source:synthetic
  • Purity:TLC 95%;GC 98%, HPLC 98%
  • Analytical Methods:TLC, GC, HPLC; identity confirmed by MS
  • Solubility:methanol, ethanol, hexane, chloroform
  • Physical Appearance:liquid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:Yes

Description

Application Notes:

Alpha-tocopherol is one of the eight forms of vitamin E and contains three methyl groups attached to the chromonal ring. Of all the forms of vitamin E, alpha-tocopherol is preferentially retained by the liver in animals and undergoes slower catabolism in cells. It has been found that alpha-tocopherol inhibits the activity of protein kinase C, an enzyme involved in cell proliferation and differentiation in smooth muscle cells, platelets, and monocytes. Other functions of alpha-tocopherol include gene regulation, up-regulation of mRNA or protein synthesis, and preventing the uptake of the harmful 7- hydroxycholesterol into cells.1 Although the antioxidant activity of alpha-tocopherol in vitro has long been established it appears that this may not be one of its primary functions in vivo.2 Vitamin E is involved in immune function, cell signaling, regulation of gene expression, and other metabolic processes. Vitamin E also inhibits lipid oxidation by donating its phenolic hydrogen to lipid free radicals.3 Antioxidant activity in vivo is normally alpha>beta>delta>gamma but the antioxidant potency may depend on various chemical and physical situations.4 The ortho-methyl substitution of the chroman head plays a vital role in the antioxidant activity of tocopherols while the phytyl tail is very important for proper positioning in the biomembranes. The antioxidant properties of vitamin E may delay memory loss in Down’s syndrome patients due to their protection from harmful oxidation caused by excess activity of superoxide dismutase. Vitamin E is only naturally produced in plants, algae, and some cyanobacteria and is therefore an important dietary nutrient for humans and animals.

References:
1. R. Brigelius and M. Traber “Vitamin E: Funcion and Metabolism” The FASEB Journal, Vol. 13(10) pp. 1145-1155, 1999
2. A. Azzi “Molecular mechanism of -tocopherol action” Free Radical Biology and Medicine, Vol. 43:1 pp. 16-21, 2007
3. G. W. Burton and K. Ingold Autoxidation of biological molecules. 1. Antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro, U. J. Am. Chem. Soc., 103, 6472-6477, 1981
4. Anchalee Sirikhachornkit, Jai W. Shin, Irene Baroli, and Krishna K. Niyogi Replacement of  -tocopherol by  -tocopherol enhances resistance to photooxidative stress in a xanthophyll-deficient strain of Chlamydomonas reinhardtii, Eukaryotic Cell, doi:10.1128, 2009
Price $145.00

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