On the Structure of Allithiamine

Abstract

Recently, Dr. Fujiwara and H. watanabe found that when thiamine is mixed with the extract of the common garlic (Allzum sativum), its thiochrome reaction, a reaction characteristic of thiamine, becomes negative. This phenomenon seems not to be caused by the decomposition of thiamine, because the reaction mixture not only regenerates thiamine by treating with a reducing agent such as cysteine or sodium hyposulfite, but also still possesses an antineuritic activity similar to that of thiamine.Therefore, it is a$sumed that in this reaction a new thiamine-like compound is produced, which was named "Allithiamine" by Dr . Fujiwara.Studies have been made on the isolation and chemical structure of allithiamine in close cooperation with Dr. Fujiwara, the result of which is described here.

Allylthiamindisulfide and Related Compounds Enhance Thermogenesis with Increasing Noradrenaline and Adrenaline Secretion in Rats.

“…Thiamin used in the present study was thiamin hydrochloride (purity 99.8%) purchased from Wako Chemical Ind., Osaka, Japan. Allylthiamindi sulfide and related compounds were prepared by Takeda Chemical Industries , Osaka, Japan (11,12), and the purity of each of these compounds was 99 .9%. The related compounds are four forms of thiamin derivatives as follows:…”

“…In contrast, allylthiamindisulfide is not water soluble but fat soluble, and the nutritional effects presumably last longer than thiamin. Matsukawa and Yurugi (11) reported that allylthiamindisulfide could be produced by the reaction between thiamin and allicin by adding thiamin directly to garlic extracts. Since that time, many related compounds have been chemically synthesized (11)(12)(13)(14).…”

“…Matsukawa and Yurugi (11) reported that allylthiamindisulfide could be produced by the reaction between thiamin and allicin by adding thiamin directly to garlic extracts. Since that time, many related compounds have been chemically synthesized (11)(12)(13)(14). Additionally, allylthiamindisulfide has been believed to have a favorable effect on human health (e. g., nutritional supply for good health and refreshment from physical fatigue), and a commercially available preparation of this compound has been used in Japan.…”

Biological Properties of a New Thiamine Derivative, Cyclocarbothiamine

“…Allithiamine is a typical example which has overcome this difficulty by modify ing the chemical structure of thiamine (8,9). Several similar compounds have been developed so far and their biological advantages may be summarized as follows.…”

Therapeutic Strategies in HTLV-I-Associated Myelopathy/Tropical Spastic Paraparesis (HAM/TSP)

“…For the stability in the blood and the efficient access of vitamin B1 to the tissues, prosultiamine was developed after allyl disulfide derived from allicin was substituted to propyl disulfide in the structure of allithiamine (Fig. (2)) [77]. Thus, Prosultiamine has a disulfide moiety in its structure as same as allicin (Fig.…”