Stability of acrylamide in model systems and its reactivity with selected nucleophiles

• Published in: Food research international Vol. 43; no. 5; pp. 1517 - 1522
• Main Authors: Adams, An, Hamdani, Samira, Lancker, Fien Van, Méjri, Slah, De Kimpe, Norbert
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.06.2010
• Subjects: Acrylamide; Amino acids; Buffers; Condensation products; Cysteine; Drying; Foods; Lysine; Michael addition; Mitigation; Nucleophiles; Stability; Mitigation; Michael addition; Acrylamide; Cysteine; Stability; Condensation products
• ISSN: 0963-9969; 1873-7145
• DOI: 10.1016/j.foodres.2010.04.033

Since the discovery of relatively high amounts of the carcinogenic acrylamide in heat-processed food products, many studies have been devoted to the formation of acrylamide. However, as acrylamide is an α,β-unsaturated amide, subsequent reactions can provoke the desired removal of this compound. Therefore, the stability of acrylamide and its reactivity with various food-relevant nucleophiles were studied. The results showed that acrylamide was quite stable in aqueous solutions, but much less in dry reaction conditions. Buffer type and pH had a significant influence on the decrease of free acrylamide. The presence of amino acids with a nucleophilic side chain considerably decreased the free acrylamide, due to Michael-type addition reactions. The highest reactivity was noted for cysteine, leading to the formation of the mono-addition product cysteine- S-β-propionamide, as well as to the double addition product. Other nucleophiles, such as lysine, arginine, serine and ascorbic acid, were less reactive, but yielded comparable condensation products.