Characterization of 2-Methyl-4-amino-5-(2-methyl-3-furylthiomethyl) pyrimidine from Thermal Degradation of Thiamin

Thiamin hydrochloride was thermally degraded in phosphate buffer (pH 6.5) at 110 degree C for 2 h. A major decomposition product was isolated by column chromatography and structurally identified by spectrometric techniques ( super(1)H NMR, super(13)C NMR, 2D NMR, and MS) as 2-methyl-4-amino-5-(2-met...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2002-07, Vol.50 (14), p.4055-4058
Main Authors: Jhoo, J-W, Lin, M-C, Sang, S, Cheng, X, Zhu, N, Stark, R E, Ho, C-T
Format: Article
Language:English
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Summary:Thiamin hydrochloride was thermally degraded in phosphate buffer (pH 6.5) at 110 degree C for 2 h. A major decomposition product was isolated by column chromatography and structurally identified by spectrometric techniques ( super(1)H NMR, super(13)C NMR, 2D NMR, and MS) as 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine (MAMP). The possible formation pathway of MAMP was studied using two model systems. It is proposed that MAMP is formed by nucleophilic attack of 2-methyl-3-furanthiol on the thiamin.
ISSN:0021-8561
DOI:10.1021/jf011591vS0021-8561(01)01591-6