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Título: | 2,4-Alkadienal trapping by phenolics |
Autor: | Hidalgo, Francisco J. CSIC ORCID ; Zamora, Rosario CSIC ORCID | Palabras clave: | Alka-2,4-dienals Carbonyl-phenol reactions Lipid oxidation Maillard reaction Reactive carbonyls |
Fecha de publicación: | 15-oct-2018 | Editor: | Elsevier | Citación: | Food Chemistry 263: 89-95 (2018) | Resumen: | Phenolics 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. | Descripción: | 30 Páginas.-- 6 Figuras.-- 3 Figuras suplementarias | Versión del editor: | http://dx.doi.org/10.1016/j.foodchem.2018.04.121 | URI: | http://hdl.handle.net/10261/175996 | ISSN: | 0308-8146 |
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