2-Methylimidazole (2-MI) and 4-methylimidazole (4-MI) can be formed via the Maillard reaction during dairy thermal treatment. In this study, different reactions between α-dicarbonyl compounds (methylglyoxal, glyoxal) and aldehydes (formaldehyde, acetaldehyde) in the presence of ammonium sulfate were performed to investigate the formation of 2-MI and 4-MI. Two formation pathways of 2-MI and 4-MI were proposed. One pathway is that α-dicarbonyl compound reacts with equivalent ammonia to form an intermediate, while aldehyde reacts with equivalent ammonia to form another intermediate, then the 2 intermediates react together to generate 2-MI or 4-MI. Alternatively, α-dicarbonyl compound can react with double ammonia to form an intermediate, and subsequently reacts with aldehyde to form 2-MI or 4-MI. Additionally, possible mechanisms were also proposed to explain the phenomenon that the 2-MI content was much lower than 4-MI in Maillard reaction.
Keywords: 2-methylimidazole; 4-methylimidazole; glyoxal; methylglyoxal.
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