Formation of 4(5)‐Methylimidazole in Aqueous d‐Glucose‐Amino Acids Model System

The International Agency for Research on Cancer (IRAC) has classified 4(5)‐methylimidazole (4‐MeI) as a group 2B possible human carcinogen. Thus, how 4‐MeI forms in a d ‐glucose (Glu) amino acids (AA) model system is important, as it is how browning is affected. An aqueous solution of Glu was mixed individually in equimolar amounts at 3 concentrations (0.05, 0.1, and 0.15 M) with aqueous solutions of l ‐Alanine (Ala), l ‐Arginine (Arg), Glycine (Gly), l ‐Lysine (Lys), and l ‐Serine (Ser). The Glu‐AA mixtures were reacted at 60, 120, and 160 °C for 1 h. The 4‐MeI levels were measured by gas chromatography‐mass spectrometry after derivatization with isobutylchloroformate. No 4‐MeI was formed at 60 °C for any treatment combination; however, at 120 °C and 0.05 M, Glu‐Arg and Glu‐Lys produced 0.13 and 0.14 mg/kg of 4‐MeI. At 160 °C and 0.05 M all treatment combinations formed 4‐MeI. At 160 °C and 0.15 M, the observed levels of Glu‐Ala, Glu‐Arg, Glu‐Gly, Glu‐Lys, and Glu‐Ser were 0.21, 1.00, 0.15, 0.22, and 0.16 mg/kg. The AA type, reactant concentrations, and temperature significantly affected (P < 0.001) formation of 4‐MeI as well as browning. Glu‐Lys treatment in all combinations produced the most browning, but Glu‐Arg produced the most 4‐MeI. This method showed that foods processed using low temperatures may have reduced levels of 4‐MeI.