Identification of acrolein as the reactive carbonyl responsible for the formation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx)

Reaction mixtures of reactive carbonyls and creatinine were submitted to high temperature and studied to identify the reactive carbonyl(s) responsible for 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) formation. MeIQx was produced by reaction of acrolein and creatinine within a wide pH range and with an activation energy of 81.1 +/- 1.4 kJ/mol. No additional reactants were required, although methylglyoxal, ammonia, and formaldehyde also participated in the reaction. Nevertheless, these additional reactants were produced in situ from either acrolein or creatinine. A reaction pathway that both explains the formation of MeIQx and is valid for the formation of other heterocyclic aromatic amines (HAAs) with the structure of quinoxaline is proposed. Obtained results demonstrate the key role of reactive carbonyls present in foods (the food carbonylome) on HAA formation. Because creatinine is ubiquitous in proteinaceous foods, the control of the food carbonylome seems to be the key point to control HAA formation in foods.

Automated summary

The reaction of acrolein and creatinine was found to produce MeIQx without the need for additional reactants. A reaction pathway explaining the formation of MeIQx and other heterocyclic aromatic amines with the structure of quinoxaline was proposed. The presence of reactive carbonyls in foods was demonstrated to play a key role in the formation of HAAs.