Contribution of Phenolic Compounds to Food Flavors: Strecker-Type Degradation of Amines and Amino Acids Produced by o- and p-Diphenols

Abstract

The ability of 20 phenolic derivatives to produce the Strecker-type degradation of phenylalanine and phenylglycine methyl ester was studied to investigate both the direct degradation of amino acids and amines by phenolic compounds in the absence of added oxidants and the effect of the number and positions of hydroxyl groups in the aromatic ring of the phenolic compound in relation to its ability to produce carbonyl derivatives from amino compounds. The obtained results showed that polyphenols can produce the Strecker degradation of amino acids and amines in the absence of added oxidants. The only requisite for producing the reaction is the presence of two hydroxyl groups in ortho or para positions. However, the presence of two hydroxyl groups in meta position in an additional aromatic ring can inhibit the Strecker-degrading ability of the hydroxyl groups in ortho or para positions. A reaction pathway that explains all of these findings is proposed. In addition, the effect of reaction conditions on the obtained reaction yields was studied. Activation energies (Ea) for phenylacetaldehyde formation from phenylalanine in the presence of hydroquinone, 1,2,4-trihydroxybenzene, and benzoquinone were 32.9, 31.5, and 28.8 kJ/mol, respectively.