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 °C for 2 h. A major decomposition product was isolated by column chromatography and structurally identified by spectrometric techniques (1H NMR, 13C NMR, 2D NMR, and MS) as 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl...

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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, Jin-Woo, Lin, Ming-Chi, Sang, Shengmin, Cheng, Xiaofang, Zhu, Nanqun, Stark, Ruth E, Ho, Chi-Tang
Format: Article
Language:English
Subjects:
Aroma and flavouring agent industries
Biological and medical sciences
Buffers
Food industries
Fundamental and applied biological sciences. Psychology
Hot Temperature
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Mass Spectrometry
Phosphates
Pyrimidines - chemistry
Pyrimidines - isolation & purification
Thiamine - chemistry
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Summary:Thiamin hydrochloride was thermally degraded in phosphate buffer (pH 6.5) at 110 °C for 2 h. A major decomposition product was isolated by column chromatography and structurally identified by spectrometric techniques (1H NMR, 13C 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. Keywords: Thiamin; thermal degradation; 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine
ISSN:0021-8561
1520-5118
DOI:10.1021/jf011591v