YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Studies on Vitamin B1 and Related Compounds. XXXIX
Structure of Allithiamine
Taizo MatsukawaShojiro Yurugi
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1952 Volume 72 Issue 12 Pages 1616-1619

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Abstract
Hydrolysis of allithiamine with hydrochloric acid was found to yield formic acid, 2-methyl-4-amino-5-aminomethylpyrimidine (I), and α-aceto-γ-hydroxypropyl allyl disulfide (II). Reduction of (II) in acetic acid solution with zinc dust yielded allylmercaptan (IV) and γ-aceto-γ-mercaptopropyl alcohol (III). Reduction of allithiamine in alcoholic hydrochloric acid with zinc dust resulted in the formation of allyimercaptan (IV) and vitamin B1 (VI). From these results, the structure of 2-[2′-methyl-4′-amino-pyrimidyl(5′)]-methylformamino-5-hydroxy-Δ2-pentenyl(3) allyl disulfide (VII) can be given to allithiamine. Further examinations were made to find which of the component of garlic bulbs reacted with vitamin B1 to form allithiamine and it was found that the latter was formed by the reaction of allicin (IX) and vitamin B1.
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© by the PHARMACEUTICAL SOCIETY OF JAPAN
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