The Formation of Acrylamide from and Its Reduction by 3-Aminopropanamide Occur Simultaneously During Thermal Treatment.

3-Aminopropanamide (3-APA) is the direct precursor of acrylamide produced in the Maillard reaction between asparagine and reducing sugars. In this research, we found that 3-APA could reduce acrylamide by the formation of adducts between acrylamide and 3-APA via Michael addition. The effects of temperature, heating duration and 3-APA/acrylamide ratio on the reduction of acrylamide were investigated. Addition of 3-APA to acrylamide at a molar ratio of 5:3 at 160 °C for 20 min reduced acrylamide by up to 47.29%. The major adduct was identified as 3,3',3'-nitrilotris, and its cytotoxicity on Caco-2 cells was evaluated to be much lower than acrylamide. The viability of Caco-2 cells retained at 88.31% and 86.43% after incubation with 16 mM 3,3',3'-nitrilotris for 24 and 48 hr, respectively, while those incubated with the same concentration of acrylamide were 23.33% and 19.12%, respectively.

PRACTICAL APPLICATION: The current study reported 3-APA could reduce acrylamide through the Micheal addition reaction between 3-APA and acrylamide. The adduct showed significantly reduced cytotoxicity compared to acrylamide. The research is critical in evaluation and control of food contaminants. The results brought new insights in the area of food safety, especially in the mechanism researches on formation and mitigation of endogenous contaminants in thermal-processed foods.