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Acrylamide Formation Mechanism in Heated Foods

Zyzak, David V., Sanders, Robert A., Stojanovic, Marko, Tallmadge, Daniel H., Eberhart, B. Loye, Ewald, Deborah K., Gruber, David C., Morsch, Thomas R., Strothers, Melissa A., Rizzi, George P., Villagran, Maria D.
Journal of agricultural and food chemistry 2003 v.51 no.16 pp. 4782-4787
acrylamides, ammonia, asparaginase, asparagine, cooking, decarboxylation, foods, heat, isotopes, mass spectrometry, schiff bases, temperature
Recent findings of a potential human carcinogen, acrylamide, in foods have focused research on the possible mechanisms of formation. We present a mechanism for the formation of acrylamide from the reaction of the amino acid asparagine and a carbonyl-containing compound at typical cooking temperatures. The mechanism involves formation of a Schiff base followed by decarboxylation and elimination of either ammonia or a substituted imine under heat to yield acrylamide. Isotope substitution studies and mass spectrometric analysis of heated model systems confirm the presence of key reaction intermediates. Further confirmation of this mechanism is accomplished through selective removal of asparagine with asparaginase that results in a reduced level of acrylamide in a selected heated food.