Use of Nucleophilic Compounds, and Their Combination, for Acrylamide Removal

Acrylamide is characterized by a conjugated structure in which an electron-withdrawing group (the amide group) is linked to a carbon–carbon double bond. Therefore, this conjugated α,β-unsaturated carbonyl structure is an electrophile that forms Michael-type adducts with nucleophiles. This reactivity has been employed for acrylamide removal, although addition of nucleophiles is complex and sometimes acrylamide increases have been observed as a consequence of collateral reactions. This chapter describes the reaction of acrylamide with thiols (cysteine and derivatives), sodium bisulfite, amino compounds (amino acids, peptides, proteins, and phospholipids), and their mixtures. Published results suggest that nucleophile ability for scavenging acrylamide is inversely correlated to the activation energy ( E a ) of the reaction (the lower the E a , the higher the decrease of acrylamide). Furthermore, the best nucleophiles for scavenging acrylamide were those that had simultaneously amino and thiol groups in the molecule. The E a of the acrylamide-scavenging ability of nucleophiles is quite low, and these reactions are produced spontaneously in the digestive tract. These reactions are assumed to be responsible for both a disappearance of acrylamide monomers during digestion and diminishing of acrylamide bioavailability.