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Antagonism between lipid-derived reactive carbonyls and phenolic compounds in the Strecker degradation of amino acids

AuthorsDelgado, Rosa M. CSIC ORCID; Hidalgo, Francisco J. CSIC ORCID ; Zamora, Rosario CSIC ORCID
KeywordsCarbonyl–amine reactions
Carbonyl–phenol reactions
Lipid oxidation
Maillard reaction
Phenolic compounds
Strecker degradation
Issue Date1-Mar-2016
CitationFood Chemistry 194: 143–1148 (2016)
AbstractThe Strecker-type degradation of phenylalanine in the presence of 2-pentanal and phenolic compounds was studied to investigate possible interactions that either promote or inhibit the formation of Strecker aldehydes in food products. Phenylacetaldehyde formation was promoted by 2-pentenal and also by o- and p-diphenols, but not by m-diphenols. This is consequence of the ability of phenolic compounds to be converted into reactive carbonyls and produce the Strecker degradation of the amino acid. When 2-pentenal and phenolic compounds were simultaneously present, an antagonism among them was observed. This antagonism is suggested to be a consequence of the ability of phenolic compounds to either react with both 2-pentenal and phenylacetaldehyde, or compete with other carbonyl compounds for the amino acids, a function that is determined by their structure. All these results suggest that carbonyl–phenol reactions may be used to modulate flavor formation produced in food products by lipid-derived reactive carbonyls.
Description25 Páginas: 1 Tabla; 5 Figuras
Publisher version (URL)http://dx.doi.org/10.1016/j.foodchem.2015.07.126
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