A Simple Procedure To Detect Lipid-Derived Carbonyl-Phenol Adducts

Abstract

Carbonyl-phenol adducts produced in the reactions of (E)-2-alkenals and (E,E)-2,4-alkadienals with phenolics were derivatized with methyl chloroformate and studied by gas chromatography–mass spectrometry to create a database that could be employed for their detection in complex mixtures of lipids and phenolics, in particular reactions involving lipid hydroperoxides. The obtained results showed that hydroperoxides produced adducts derived from acrolein, crotonaldehyde, and 2-pentenal when the 13-hydroperoxide of methyl linolenate was used, and acrolein and 2-octenal when the 13-hydroperoxide of methyl linoleate was employed. On the contrary, adducts derived from (E,E)-2,4-alkadienals could not be detected in these mixtures. Although only two types of lipid-derived aldehydes have been studied, the obtained results support that this methodology can be extended to other lipid oxidation products and phenolics and employed to quantitatively determine carbonyl-phenol adduct content. Therefore, this methodology may constitute a powerful tool to investigate the formation of carbonyl-phenol adducts in complex systems.