The decarboxylation of phenylalanine in the presence of methyl 13-hydroperoxyoctadeca-9,11-dienoate (LOOH), 2,4-decadienal (DD), 4,5-epoxy-2-decenal (ED), 4-hydroxy-2-nonenal (HN), and 4-oxo-2-nonenal (ON) was studied both to explore the potential of lipid oxidation products (LOP) to produce amino acid decarboxylation and to understand the reaction pathways responsible for this degradation. All assayed LOP were able to decarboxylate phenylalanine, but their reactivity decreased in the following order when the reaction was carried out under non-oxidative conditions: DD>ED≈LOOH>HN≈ON.