H2 THE SIMPLER NATURAL BASES 



Funk [1911] in England, and Suzuki with Shimamura and 

 Odake [1912] in Japan, showed independently and about the same 

 time that the substance is a base, is present in very small amount, and 

 has great curative action. To Funk belongs the further credit of 

 having been the first to analyse the substance and to isolate the same 

 or a similar body from yeast. Chemical work in this direction has 

 also been done by Schaumann [1912, I], Moore and his collaborators 

 [1912], Cooper [1913] and others. 



In spite of the discrepancies which exist between the statements of 

 various authors, it seems fairly well established that the curative sub- 

 stance in rice polishings, for which Funk has suggested the name 

 vitamine and which Suzuki and his collaborators call oryzanine, is a 

 base which can be extracted by water and by alcohol, but not by 

 acetone or ether. It is precipitated by phosphotungstic acid, by 

 tannin, by mercuric chloride in alcoholic solution and by silver nitrate 

 and baryta. The latter property indicates the presence of an imino- 

 group. The mercurichloride is soluble in boiling water. 



Suzuki, Shimamura and Odake describe a crystalline picrate of 

 their substance, which they did not however analyse. Funk, by 

 utilising the properties indicated above, obtained from rice polishings 

 a minute yield of a crystalline substance, to which he assigned the 

 formula C 17 H 2o O 7 N 2 , but more recently [1913], by fractional crystal- 

 lisation, he separated it into two substances ; one of these was found 

 to give the following average analytical results: C = 58*85 percent., 

 H = 3-9 per cent, N = 10*6 per cent. ; it melted at 233. The other 

 gave on the average C = 58*4 per cent, H = 4*0 per cent, N = 1 1*05 

 per cent, and melted at 234. The latter was identified as nicotinic 

 acid, C 6 H 5 O 2 N, which, in the pure state, is inactive and had already 

 been obtained from rice by Suzuki. To the former substance Funk 

 gave the formula C 26 H 20 O 9 N 4 and he stated that it is a tetrabasic acid. 

 It is considered by Funk to be the chief curative substance in rice 

 polishings. Funk separated the " vitamine " fraction of yeast, which 

 he at first considered to be identical with that of rice, into nicotinic 

 acid and an active principle melting at 229 (corr.) which when dried in 

 vacuo at room temperature has the formula C 26 H 21 O 9 N 6 , but dried at 

 1 00 changes to C 24 H 19 O 9 N 5 , implying the somewhat unusual loss of 

 two carbon and two hydrogen atoms. 



It will be seen that the substance C 26 H 20 O 9 N 4 obtained from rice 

 has a very close resemblance to nicotinic acid, both as regards melting 

 point and chemical composition, and at present the possibility does not 

 seem completely excluded, that this body is merely nicotinic acid con- 



