Formation of acrylamide in the presence of quinones

The degradation of asparagine by either hydroxytyrosol quinone or caffeic acid quinone was studied to clarify the ability of phenolics, and their corresponding quinones, in the promotion/inhibition of acrylamide production. Formed acrylamide increased at pH 4-6, in the presence of oxygen and a small amount of water, and with increased reaction times and temperatures. The activation energy for the reaction was 56.5-61.5 kJ/mol. The amount of acrylamide produced by both carbohydrate-derived reactive carbonyls and quinones was similar when starting from both asparagine and 3-aminopropionamide. Obtained results suggested that acrylamide was produced by quinones analogously to other reactive carbonyls and a reaction pathway was proposed. Additional experiments showed that the ability of phenolics to produce acrylamide was related to their ability to be transformed into quinones (their oxidability). In addition, when other carbonyls were present, significant changes were observed and the phenolic carbonyl-trapping ability also played a major role.