Chapter XD 



THIAMINE* 



Introduction 



Between 1884 and 1912, it was established that beriberi in man 1 > 2 - 3 

 and polyneuritis (beriberi) in fowls 4 and in rats 5 are deficiency diseases 

 caused by the lack of some substance which is present only in certain 

 foods, and it was shown that rice bran is a relatively rich source of this 

 necessary substance. The isolation of this substance (which in the Euro- 

 pean literature is known as aneurine and in the American literature is 

 called thiamine) presented many difficulties; it was not until 1926 to 1934 

 that crystalline preparations approaching purity were obtained 6 ~ 10 and 

 the empirical formula was established beyond reasonable doubt. In 1936, 

 Williams u and, independently, Grewe 12 showed that thiamine has the 

 structure represented by the following formula: 



ci- 



CH 2 N+ C— CH 3 



CH 3 — '^ ^J— NH 2 HC C— CH 2 CH 2 OH 



* \/ 



S 



thiamine 



Synthesis of this compound was achieved in the same year by Williams 

 and Cline 13 and by Andersag and Westphal. 14 



Specificity 



The results of tests on pigeons and on rats indicate that on a molar 

 basis, the hydrochloride, hydrobromide, 13 hydroiodide, 15 the sulfate and 

 nitrate salts as well as the acetate, benzoate, chaulmoograte and phos- 

 phate esters 17 of thiamine possess substantially the same antineuritic 

 activity. 



Thiamine in the form of the pyrophosphate ester (cocarboxylase) is 

 involved in tissue oxidation of carbohydrates, particularly in reactions 

 involving decarboxylation of pyruvic acid; 18 consequently, it might be 

 expected that thiamine would be capable of reversible oxidation and 



* By A. D. Barton and Lorene L. Rogers. 



684 



