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The Isolation from Wheat Germ Oil of an Alcohol, α-Tocopherol, Having the Properties of Vitamin E

Herbert M. Evans, Oliver H. Emerson, Gladys A. Emerson
DOI: http://dx.doi.org/10.1111/j.1753-4887.1974.tb06280.x 80-82 First published online: 1 March 1974

Abstract

We have prepared from the non-saponifiable matter of wheat germ oil thress aflophanates:

1. M.p. 250°. This is a possibly the allophante of β-amyrin. The alcohol regenrated from the allopohante has no vitamin E potency.

2. M.p. 138°, readily crystallizing in long needles. The analysis agree with values required by monollophantes of an alcohol, C39H50O2. The alcohol from this allophante apparenelly has some vitamin E potency, but less than that from the third allophanate.

3. M.p. 158-160°. From this allophanate, the alcohol—for which we propose the name α-tocopherol—when given in a single dose of 3 mg. always enables vitamin E-deficient rats to bear young. α-Tocopherol shows a characteristic absoption band at 2980 Å., E1 per cent1 cm. = 90 ca. Treatment with methyl alcoholic silver nitrate converts it to a substance which has absorption bands at 2710 and 2620 Å respectively, E1 per centcm. = 480 ca., and possesses and some vitamin E activity.

α-Tocopherol yields a crystaline p-nitrophenylurethane melting at 120-131°. Analyses of both the urethane and the allophanate indicate a provisional formula for α-tocopherol of C29H50O2

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