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Formation of Carcinogenic 4(5)-methylimidazole in Maillard Reaction Systems

Formation of Carcinogenic 4(5)-methylimidazole in Maillard Reaction Systems

Joon-Kwan Moon, Takayuki Shibamoto

J Agric Food Chem. 2011 Jan 26;59(2):615-8.

PMID: 21186780

Abstract:

4(5)-Methylimidazole has received the attention of federal and state regulatory agencies because of its carcinogenicity and common presence in foods and beverages. In the present study, the formation of 4(5)-methylimidazole in Maillard reaction model systems consisting of D-glucose/NH(3), L-rhamnose/NH(3), methylglyoxal/NH(3), and methylglyoxal/formaldehyde/NH(3) was investigated. 4(5)-Methylimidazole was formed at levels ranging from 0.49 to 0.71 mg/mL in the d-glucose/NH(3) model system. The formation of 4(5)-methylimidazole was slightly higher in the L-rhamnose/NH(3) system (0.91 mg/mL) than in the d-glucose/NH(3) system (0.71 mg/mL) under the conditions used in the present study. A methylglyoxal/NH(3) system produced significantly higher levels of 4(5)-methylimidazole (5.70 mg/mL), suggesting that methylglyoxal is an important precursor of 4(5)-methylimidazole. Ammonolysis of methylglyoxal, which is one of the glucose degradation products, was proposed to form formamide, which subsequently reacted with 2-aminopropanal (α-aminocarbonyl intermediate) formed from methylglyoxal to give 4- or 5-methylimidazole. The levels of 4(5)-methylimidazole found in commercial cola soft drinks range from 0.30 μg/mL (brand 3) to 0.36 μg/mL (brands 1 and 5).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP822366	4(5)-Methylimidazole		822-36-6	Price

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