title: Characterization of 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine from thermal degradation of thiamin.
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.
authors.affiliation: Department of Food Science, Rutgers University, 65 Dudley Road, New Brunswick, New Jersey, 08901, USA.
authors.forename: Jin-Woo
authors.initials: JW
authors.lastname: Jhoo
authors.forename: Ming-Chi
authors.initials: MC
authors.lastname: Lin
authors.forename: Shengmin
authors.initials: S
authors.lastname: Sang
authors.forename: Xiaofang
authors.initials: X
authors.lastname: Cheng
authors.forename: Nanqun
authors.initials: N
authors.lastname: Zhu
authors.forename: Ruth E
authors.initials: RE
authors.lastname: Stark
authors.forename: Chi-Tang
authors.initials: CT
authors.lastname: Ho
mesh_terms: 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*
chemical_list: C463488:2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimdiine; D002021:Buffers; D010710:Phosphates; D011743:Pyrimidines; D013831:Thiamine