Characterization of 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine from thermal degradation of thiamin

J Agric Food Chem. 2002 Jul 3;50(14):4055-8. doi: 10.1021/jf011591v.

Abstract

Thiamin hydrochloride was thermally degraded in phosphate buffer (pH 6.5) at 110 degrees C for 2 h. A major decomposition product was isolated by column chromatography and structurally identified by spectrometric techniques ((1)H NMR, (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.

MeSH terms

  • Buffers
  • Hot Temperature*
  • Hydrogen-Ion Concentration
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Phosphates
  • Pyrimidines / chemistry*
  • Pyrimidines / isolation & purification*
  • Thiamine / chemistry*

Substances

  • 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimdiine
  • Buffers
  • Phosphates
  • Pyrimidines
  • Thiamine