The most extensive investigations have dealt with the first type
discovered, namely the vitamine "B" or Funk antineuritic type. In 1911
Cooper and Funk found that the alcoholic extract of rice polishings could
be precipitated with phosphotungstic acid and that this procedure
permitted them to obtain a fraction that was particularly potent and free
from proteins, carbohydrates, and phosphorus. Funk carried this
investigation farther and fractioned the phosphotungstic acid precipitate
with silver nitrate, following the usual procedure for separating
nitrogenous bases. From the silver-nitrate baryta fraction he obtained a
crystalline complex melting at 233°C. to which he gave the formula
C_17H_20O_7N_2. This substance was curative for pigeons and the
fractioning process was applied by him to yeast and other foodstuffs with
similar results. From these results Funk believed the vitamine to belong
to a class of substances known as the pyrimidine bases. Later, when
working with Drummond, Funk was forced to admit that his crystalline
complex was not the pure substance, as analysis showed that it contained
large amounts of nicotinic acid. His product might well be considered as
nicotinic acid contaminated with vitamines.
Suzuki, Shimamura and Odake also used the phosphotungstic precipitation
method and claimed to have prepared the crystalline antineuritic substance
which they called oryzanin in the form of a crystalline picrate. Drummond
and Funk repeated this work, but were unable to confirm the Japanese
results. A group of British chemists (Edie, Evans, Moore, Simpson and
Webster) obtained an active fraction from yeast and succeeded in
separating this into a crystalline basic member belonging to the
pyrimidine group which they called _torulin_.
None of these three preparations have stood the test of analysis however
and their curative properties seem to lie in their greater or less
contamination with the actual substance, whatever it is. Numerous
modifications of the fundamental method for extracting the substance have
been planned and executed. Funk for example has shown that if the
phosphotungstic precipitate is treated with acetone it is possible to
separate it into an acetone soluble and an acetone-insoluble fraction and
that the curative fraction is in the latter. McCollum has reported that
while ether, benzene and acetone cannot be used to extract the B vitamine
from its source, benzene, (and to a slight extent acetone) will dissolve
the vitamine if it is first deposited from an alcohol extract on dextrin.
These observations have not yielded any further clew to the nature of the
substance.
Public-domain text, read in full here on John Shaqi.
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