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 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.
Jhoo
Jin-Woo
JW
Department of Food Science, Rutgers University, 65 Dudley Road, New Brunswick, New Jersey, 08901, USA.
Lin
Ming-Chi
MC
Sang
Shengmin
S
Cheng
Xiaofang
X
Zhu
Nanqun
N
Stark
Ruth E
RE
Ho
Chi-Tang
CT
D002021:Buffers; D006358:Hot Temperature; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010710:Phosphates; D011743:Pyrimidines / Q000737:chemistry* / Q000302:isolation & purification*; D013831:Thiamine / Q000737:chemistry*
C463488:2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimdiine; D002021:Buffers; D010710:Phosphates; D011743:Pyrimidines; D013831:Thiamine