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2-Alkenal-scavenging ability of m-diphenols

AuthorsHidalgo, Francisco J. CSIC ORCID ; Zamora, Rosario CSIC ORCID
KeywordsCarbonyl–phenol reactions
Lipid oxidation
Carbonyl–phenol adducts
Issue Date2014
CitationFood Chemistry 160: 118- 126 (2014)
AbstractThe reaction between m-diphenols (resorcinol, 2-methylresorcinol, 2,5-dimethylresorcinol, 3-methylphenol, orcinol, and phloroglucinol) and 2-alkenals (2-pentenal and 2-octenal) was studied in an attempt to understand the chemical pathways involved in the scavenging ability of m-diphenols for the 2-alkenals produced as a consequence of lipid oxidation. Phenols reacted chemically with 2-alkenals producing a number of 2H-chromenols, chromandiols, chromanols, and dihydropyrano[3,2-g]chromenes, which were isolated and identified by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). The identification of all these compounds resulted in the construction of a general pathway for these reactions. These results confirm that the 2-alkenal-scavenging ability of m-diphenols is a consequence of their structure. This is a complex reaction in which many different products are formed. The most stable products were the chromandiols. However, the main reaction products were the 2H-chromenols. These products were unstable and disappeared as a consequence of polymerisation and browning reactions. © 2014 Elsevier Ltd. All rights reserved.
Identifiersdoi: 10.1016/j.foodchem.2014.03.071
issn: 1873-7072
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