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Role of bioactive carbonyl compounds on the conversion of asparagine into acrylamide during heating

Hamzalıoğlu, Aytül, Gökmen, Vural
European food research & technology 2012 v.235 no.6 pp. 1093-1099
Maillard reaction, acrylamides, ascorbic acid, asparagine, bioactive properties, carbonyl compounds, curcumin, dehydroascorbic acid, fructose, mass spectrometry, melting point, models, silymarin, vanillin
Role of bioactive carbonyls on the conversion of asparagine into acrylamide during heating under low moisture conditions was investigated using different binary and ternary models. Ascorbic acid, dehydroascorbic acid, curcumin, silymarin, vanillin, and as well as fructose were used to understand their efficiency on acrylamide formation and to identify key intermediates formed in the Maillard reaction during heating at 180 °C. All carbonyls generated significant amounts of acrylamide from asparagine. Their efficiency were in the order of vanillin > fructose > silymarin > ascorbic acid > curcumin > dehydroascorbic acid. High-resolution mass spectrometry analyses of heated reaction mixtures confirmed the presence of Schiff bases of asparagine with given carbonyl and their decarboxylated forms with very high mass accuracy (∆ < 2.0 ppm). There was an inverse relationship between the melting point of carbonyls and the conversion ratio of asparagine. Vanillin having a melting point of 84 °C formed the highest amount of acrylamide. Presence of 1.0 % of vanillin increased acrylamide formation more than 2 times in a crust resembling model system.