Description
Polyunsaturated fatty acids such as arachidonate and linoeate, while essential to health maintenance, are subject to random peroxidation by ambient oxygen, resulting in fragmented and reactive decomposition products. One prominent autoxidation product of either trilinolein or arachidonic acid is
trans-
4,5-
epoxy-
2(E)-
decenal. This aldehyde is responsible for a pungent metallic flavor of decomposed lipids, with a detection threshold of 1.5 pg/l in air.
trans-
4,5-
epoxy-
2(E)-
Decenal also reacts with nucleophiles (lysine amino groups) on proteins, leading to loss of cell function and viability. This reactive aldehyde is therefore a useful tool in elucidating the effects of peroxidative damage in experimental models.
Uses
trans-4,5-Epoxy-(E)-2-decenal is an oxygenated α,β-unsaturated aldehyde found in mammalian blood that gives blood its characteristic metallic odor. It is used by predators to locate blood or prey[1].
References
[1] Lee SH,et al. 4,5-Epoxy-2(E)-decenal-induced formation of 1,N(6)-etheno-2'-deoxyadenosine and 1,N(2)-etheno-2'-deoxyguanosine adducts. Chem Res Toxicol. 2002 Mar;15(3):300-4. DOI:
10.1021/tx010147j
