Model reactions of acrylamide with selected amino compounds.J Agric Food Chem. 2010 Feb 10; 58(3):1708-13.JA
The reaction of acrylamide with amines, amino acids, and polypeptides was studied in an attempt to understand the role of amino compounds on acrylamide fate. The obtained results showed that amino compounds are added to acrylamide by means of a Michael addition to produce the corresponding 3-(alkylamino)propionamides. Although 3-(alkylamino)propionamides can also be added to a new molecule of acrylamide to produce a new adduct, this last adduct was not detected under the employed conditions in which the concentration of acrylamide was much lower than the concentration of the amino compounds. The produced 3-(alkylamino)propionamides were not stable, and the addition reaction was easily reversed by heating. Thus, acrylamide was produced from 3-(alkylamino)propionamides by means of an elimination reaction. However, the activation energies (E(a)) of both reactions are not the same. In fact, acrylamide seems to be converted into its Michael adduct with a lower activation energy than the elimination reaction of the Michael adduct. For this reason, when acrylamide was stored in the presence of glycine at 60 degrees C, acrylamide disappeared after 14 days. However, when these samples were heated again for 20 min at 180 degrees C, the equilibrium was reestablished and a significant amount of acrylamide was detected. All of these results suggest that amino compounds may play a significant role in the changes observed in acrylamide content in foods upon storage. In addition, they also point to 3-(alkylamino)propionamides as possible compounds in which acrylamide might be potentially hidden.