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Vitamin E


DATA No : VVE0001 INFORMANT : Fumiko Hirahara

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

COMMON NAME: RRR-a-tocopherol d-a-tocopherol
SYMBOL: RRR-a-Toc/d-a-Toc
FORMULA: C29H50O2 MOL.WT (average) : 430.706


Download ChemDraw structure data
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.
[Table 0008]
[Table 0009] RRR-a-tocopherol has been assigned an activity of 1 mg a-TE per mg.
[Table 0010] (Ref. 0034/0035/0036)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:a5461-25.gif" HEIGHT="16" WIDTH="22" ALT="546.1-25">=+0.32deg in ethanol/d5461-25.gif" HEIGHT="16" WIDTH="22" ALT="546.1-25">=-3.0deg in benzene (Ref. 0001)

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:292nm, E1%1cm=75.8(ethanol)

IR SPECTRA:3310,2930,1620,1590,1460,1375,1270,1160,850cm-1

NMR SPECTRA:NMR spectrometry(60 MHz:CDCl3)
[Spectrum 0001] (Ref. 0032)

MASS SPECTRA:

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
1.High linoleic acid type margarine 2.Sunflower oil 3.Cottonseed oil 4.Wheat germ 5.Roasted and salted sweet almond 6.Safflower oil 7.Rice bran oil 8.Roasted hazelnuts 9.Dried sunflower seeds 10.Anglerfish liver 11.Roasted Pine nuts 12.Virginia type dried peanuts 13.Spanish type dried peanuts 14.Salted roe 15.Uncooked and salted pollack roe 16.Palm oil 17.Cultured fish 18.Olive oil 19.Fried potato chips 20.Black karinto 21.Age-senbei 22.Raw roe (Ref. 0003/0004/0005/0006/0007/0033/0034)
CHEMICAL SYNTHESIS
The positively rotating formylchroman compound is condensed with the C15-phosphonium bromide to give (2S,4'R,8'R)-1',2'-dehydro-a-tocopherol acetate. After catalytic hydrogenation of the double bond and hydrolysis of the acetate grouping, (2R,4'R,8'R)-a-tocopherol is produced.
[Table 0003] (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. 0043)
GENETIC INFORMATION
Ataxia with vitamin E deficiency (AVED), or familial isolated vitamin E deficiency, is a rare autosomal recessive neurodegenerative disease characterized clinically by symptoms with often striking resemblance to those of Friedreich ataxia. (Ref. 0042)
NOTE

REFERENCES
[0001]
AUTHOR:Kasparek,S.(1980)Chemistry of Tocopherols and Tocotrienols, in Vitamin E, a comprehensive Treasure (Machlin, L.J. ,eds.), PP7-65, Marcel Dekker, INC., New York and Basel
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0002]
AUTHOR:RRR-a-tocopherol,all-rac-a-tocopherol(1998), in European Pharmacopoeia-Supplement (Council of Europe eds.) , pp486-489
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0003]
AUTHOR:Standard Tables of Fat-soluble Food Composition in Japan (1995) Fatty Acid,Cholesterol,Vitamin E( the Science and Technology Agency,eds),,pp13-103, Ishiyaku Press Ltd. (Japan),Tokyo
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0004]
AUTHOR:Sheppard, A.J., Pennington,A.T.(1993) Analysis and Distribution of Vitamin E in Vegetable Oils and Foods, in Vitamin E in Health and Disease (Packer, L. , Fuchs, J. eds.),pp9-31,Marcel Dekker Inc , New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0005]
AUTHOR:Goh S. H. , Choo, Y. M. and Ong, S. H.
TITLE:
JOURNAL:J. Amer. Oil Chem. Soc.
VOL:62 PAGE : 237 -240 (1985)
[TOP]

[0006]
AUTHOR:Leth, T., and Sondergaard, H.
TITLE:Biological activity of vitamin E compounds and natural materials by the resorption-gestation test, and chemical determination of the vitamin E activity in foods and feeds PubMed ID:925769
JOURNAL:J Nutr.
VOL:107 PAGE : 2236-2243 (1977)
[TOP]

[0007]
AUTHOR: Evans H.M., Emerson,O.H. and Emerson,G.A.
TITLE:The Isolation from Wheat Germ Oil of an Alcohol, a-Tocopherol, having the Properties of Vitamin E.
JOURNAL:J. Biol. Chem.
VOL:113 PAGE : 319 -332 (1936)
[TOP]

[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
TITLE:
JOURNAL:
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[0032]
AUTHOR:Katui,G.(1980) Chemistry of Vitamin E and Its Related Compounds, in Vitaminology [1], Fat-soluble Vitamins (Japanese Vitamin Society eds.), pp183-193, Tokyo Kagaku Dojin,Tokyo
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0033]
AUTHOR:Ong,A.S.H.(1993) Natural Sources of Tocotrienols, in Vitamin E in Health and Disease (Packer,L. and Fuchs,J. eds) ,pp3-8,Marcel Dekke,Inc., New York,Basel,Hong Kong
TITLE:
JOURNAL:
VOL: PAGE : - ()
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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
TITLE:
JOURNAL:
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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)
[TOP]

[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
TITLE:
JOURNAL:
VOL: PAGE : - ()
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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
TITLE:
JOURNAL:
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[0042]
AUTHOR:Cavalier, L., Ouahchi, K., Kayden, H. J., Di Donato, S., Reutenauer, L., Mandel, J. L., and Koenig, M.
TITLE:Ataxia with isolated vitamin E deficiency: heterogeneity of mutations and phenotypic variability in a large number of families PubMed ID:9463307
JOURNAL:Am J Hum Genet.
VOL:62 PAGE : 301-310 (1998)
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[0043]
AUTHOR:Traber, M. G., Elsner, A., and Brigelius-Flohe, R.
TITLE:Synthetic as compared with natural vitamin E is preferentially excreted as alpha-CEHC in human urine: studies using deuterated alpha-tocopheryl acetates PubMed ID:9804189
JOURNAL:FEBS Lett.
VOL:437 PAGE : 145-148 (1998)
[TOP]

[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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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.