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Título: | Characterization of Carbonyl-Phenol Adducts Produced by Food Phenolic Trapping of 4-Hydroxy-2-hexenal and 4-Hydroxy-2-nonenal |
Autor: | Hidalgo, Francisco J. CSIC ORCID ; Zamora, Rosario CSIC ORCID | Palabras clave: | Reactive carbonyls Phenolics Maillard reaction Lipid oxidation HHE 4-hydroxy-2-alkenals HNE Carbonyl–phenol reactions |
Fecha de publicación: | 2019 | Editor: | American Chemical Society | Citación: | Journal of agricultural and food chemistry 67: 2043- 2051 (2019) | Resumen: | 4-Hydroxy-2-alkenals disappear in the presence of food phenolics (i.e., cathechin or quercetin), and the corresponding carbonyl–phenol adducts are produced. In an attempt to identify structure(s) of formed adducts, the reactions between model phenolics (resorcinol, 2-methylresorcinol, orcinol, and 2,5-dimethylresorcinol) and hydroxyalkenals (4-hydroxy-2-hexenal and 4-hydroxy-2-nonenal) were studied and the produced adducts were isolated by column chromatography and unambiguously characterized by one- and two-dimensional nuclear magnetic resonance and mass spectrometry as dihydrobenzofuranols (1), chromane-2,7-diols (2), and 2H-chromen-7-ols (3). These compounds were mainly produced at slightly basic pH values and moderate temperatures. Their activation energies (Ea) of formation were ∼25 kJ mol–1 for adducts 1, ∼32 kJ mol–1 for adducts 2, and ∼38 kJ mol–1 for adducts 3. A reaction pathway that explains their formation is proposed. All of these results confirm that, analogously to other lipid-derived carbonyl compounds, phenolics can trap 4-hydroxy-2-alkenals in an efficient way. Obtained results provide the basis for the potential detection of carbonyl–phenol adducts derived from hydroxyalkenals in food products. | URI: | http://hdl.handle.net/10261/182379 | DOI: | 10.1021/acs.jafc.8b07091 | Identificadores: | doi: 10.1021/acs.jafc.8b07091 issn: 1520-5118 |
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