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2,4-Alkadienal trapping by phenolics

AuthorsHidalgo, Francisco J. CSIC ORCID ; Zamora, Rosario CSIC ORCID
Carbonyl-phenol reactions
Lipid oxidation
Maillard reaction
Reactive carbonyls
Issue Date15-Oct-2018
CitationFood Chemistry 263: 89-95 (2018)
AbstractPhenolics can trap lipid-derived reactive carbonyls as a protective function that diminishes the broadcasting of the lipid oxidative damage to food macromolecules. In an attempt to clarify the trapping of 2,4-alkadienals by phenolics, this study analyzes the reactions of 2,4-hexadienal, 2,4-heptadienal, and 2,4-decadienal with 2-methylresorcinol. These reactions produced (E)-4-(alk-1-en-1-yl)-8-methyl-2,7-bis(prop-1-en-2-yloxy)chromanes, which were isolated and characterized by 1D and 2D NMR and MS. Carbonyl-phenol adduct formation was favored at pH > 7 and moderate temperatures (25–80 °C). Adducts were quantified and shown to be produced as a mixture of diastereomers. Diastereomers 2R,4S plus 2S,4R were formed to a higher extent than diastereomers 2R,4R plus 2S,4S under the different conditions assayed, although activation energies (Ea) for the formation of all of them was mostly the same (∼62 kJ·mol−1). These results show that phenolics can trap 2,4-alkadienals and provide the basis for the later detection of the formed adducts in food pro[ducts.
Description30 Páginas.-- 6 Figuras.-- 3 Figuras suplementarias
Publisher version (URL)http://dx.doi.org/10.1016/j.foodchem.2018.04.121
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