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Vitamin E


DATA No : VVE0004 INFORMANT : Fumiko Hirahara

NAME : 2RS-(4'RS,8'RS,12'-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol

COMMON NAME: all-rac-a-tocopherol
SYMBOL: all-rac-a-toc
FORMULA: C29H50O2 MOL.WT (average) : 430.706


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BIOLOGICAL ACTIVITY
The true biological activity of vitamin E is determined by its ability to prevent or reverse specific vitamin E deficiency symptoms in animal in vivo (e.g., fatal resorption, muscular dystrophy, and encephlomalacia). Other tests, such as the erythrocyte hemolysis test and elevation of plasma tocopherol, have been used. RRR-a-tocopherol has been reported as 135-194% more than all-rac-a-tocopherol when evaluated by the rat resorption-gestation test , about 200% in terms of tissue retention of deuterated tocopherols in rat and human. The relationship between a-tocopherol and its derivatives was announced by USP.
[Tables 0008/0009) RRR-a-tocopherol has been assigned an activity of 1 mg a-TE per milligram.
[Table 0010] (Ref. 0034/0035/0036)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

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OPTICAL ROTATION:

DENSITY:

SOLUBILITY:practically insol in water , freely sol in acetone, in ethanol, in ether, in methylene chloride and in fatty oils (Ref. 0002)
SPECTRAL DATA
UV SPECTRA:

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OTHER SPECTRA:
CHROMATOGRAM DATA
Many analytical methods (colorimetric, fluorometric,TLC,GC,HPLC) have been reported for the determination of Tocopherols and tocotrienols. At the present time, HPLC methods are popular for the analysis of vitamin E.
[Chromatogram 0005] (Ref. 0038)
SOURCE

CHEMICAL SYNTHESIS
(2RS,4'RS,8'RS)-a-tocopherol was synthesized from trimethylhydroquinone and racemic phytol.
[Table 0002] (Ref. 0008)
METABOLISM
The apparent absorption of RRR-a-tocopherol in human is found to be similar whether administered as the free phenol, the acetyl ester, or the succinyl ester.(Ref. 0044) All-rac-a-tocopherol compared with RRR-a-tocopherol is preferentially metabolized to a-CEHC and excreted.(Ref. 0044)
GENETIC INFORMATION

NOTE

REFERENCES
[0002]
AUTHOR:RRR-a-tocopherol,all-rac-a-tocopherol(1998), in European Pharmacopoeia-Supplement (Council of Europe eds.) , pp486-489
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[0008]
AUTHOR:Isler, O., Mayer,H.(1971) [227]Synthesis of Vitamin E , in Methods in Enzymnology vol.18 (McCormick, D,B.,Wright,L. D eds.),pp241-348, Academic Press, New York and London
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[0034]
AUTHOR:Kijima,S. (1993) Chemistry of Vitamin E, in Vitamin E, Its Usefulness in Health and in Curing Disease (Mino,M., Nakmura,H., Diplock,A. and Kayden,H.J. eds),pp3-11,Japan Scientific Societies Press
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[0035]
AUTHOR:Burton, G. W., Traber, M. G., Acuff, R. V., Walters, D. N., Kayden, H., Hughes, L., and Ingold, K. U.
TITLE:Human plasma and tissue alpha-tocopherol concentrations in response to supplementation with deuterated natural and synthetic vitamin E PubMed ID:9537614
JOURNAL:Am J Clin Nutr.
VOL:67 PAGE : 669-684 (1998)
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[0036]
AUTHOR:Sheppard,A.J., Pennington,A.T. and Weihrauch,J.L.(1993) Analysis and Distribution of Vitamin E in Vegetable Oils and Foods in Vitamin E in Health and Disease (Packer,L. and Fuchs,J. eds) ,pp9-31,Marcel Dekke,Inc., New York,Basel,Hong Kong
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[0038]
AUTHOR:Abe,K. and Matsumoto,A.(1993) Quantitative Determination of Tocopherols, Its Usefulness in Health and in Curing Disease (Mino,M., Nakmura,H., Diplock,A. and Kayden,H.J. eds),pp13-19,Japan Scientific Societies Press
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[0044]
AUTHOR:Traber, M. G., and Sies, H.
TITLE:Vitamin E in humans: demand and delivery PubMed ID:8839930
JOURNAL:Annu Rev Nutr.
VOL:16 PAGE : 321-347 (1996)
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