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Formation of 3-hydroxypyridines by lipid oxidation products in the presence of ammonia and ammonia-producing compounds

AuthorsHidalgo, Francisco J. CSIC ORCID ; Lavado-Tena, Cristina M.; Zamora, Rosario CSIC ORCID
KeywordsCarbonyl-amine reactions
Lipid oxidation
Maillard reaction
Reactive carbonyls
Issue Date30-Oct-2020
CitationFood Chemistry 328: 127100 (2020)
AbstractPyridines are produced during food processing and are important flavor compounds. In spite of that, their formation pathways are still poorly understood, in particular those related to 3-hydroxypyridines. In an attempt to fill this gap, this study describes, for the first time, precursors and reaction pathways leading to 3-hydroxypyridine formation. 3-Hydroxypyridines are produced by reaction of lipid-derived reactive carbonyls and ammonia-producing compounds and were studied by using gas chromatography coupled to mass spectrometry. Their main precursors resulted to be 4,5-epoxy-2-alkenals and 2,4-alkadienals. 3-Hydroxypyridines were produced at temperatures higher than 100 °C, at slightly basic pH values, and with an activation energy of about 50 kJ/mol. A reaction pathway that explains their formation in the course of the lipid oxidation pathway is proposed. The role of lipid oxidation on the production of 3-hydroxypyridines was confirmed by studying their formation in oxidized linseed and menhaden oils heated in the presence of glutamine.
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