Oxo Thiamine is a thiamine derivative featuring a thiazole ring fused to a pyrimidine moiety via an oxo-substituted methylene bridge. The compound exhibits a 2-methyl-4-amino-5-hydroxymethyl thiazole unit linked to a 4-methyl-5-pyrimidinyl disulfide, with an additional carbonyl group (C=O) oxidized at the methylene bridge compared to the parent thiamine structure. This oxidation introduces a ketone functionality, altering its redox properties and stability. The compound arises as a synthetic byproduct during thiamine oxidation processes, particularly under alkaline or aerobic conditions. Its distinct UV absorption and chromatographic profile enable its identification as a critical impurity in thiamine API batches, serving as an HPLC reference standard for impurity quantification.
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InChI=1S/C12H16N4O2S/c1-7-10(3-4-17)19-12(18)16(7)6-9-5-14-8(2)15-11(9)13/h5,17H,3-4,6H2,1-2H3,(H2,13,14,15)
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