Abstract
O. Bessey (J. Biol. Chem. 195,453,1952) inactivated thiamine in its alkaline solution with benzenesulfonyl chloride for the purpose of estimating thiamine in biological materials. We isolated 4.3g crystals of mp. 97° after standing the reaction mixture of 10g thiamine-hydrochloride in 40cc of 30% NaOH-solution with 10.5g benzenesulfonyl chloride for a night. After its recrystallization from acetone or alcohol, prisms of mp. 113-114°(I) were obtained and they lost 2 moles of crystalline water on drying in vacuum. The analysis shows its empirical formula (anbydrous) as C_<12>H_<16>ON_4S and the substance can not be carried back to thiamine by cysteine treatment or any other means. (I) is easily hydrolysed by HCl into 2-methyl-4-amino-5-aminomethyl-pyrimidine (II) and oily substances of bp_4 41〜42° (III)and bp_4 121〜125°. (III) agrees with C_5H_6OS. (I) is oxidized its sulfoxide (IV) by hydrogen peroxide in 50% acetic acid. We tentatively designate (I) as thiamine-anhydride ; its chemical structure and the degradation schema by HCl will be shown as follows
