(e)-2-hexadecenal

Sphingosine-1-phosphate (S1P), a bioactive lipid crucial in numerous signaling pathways, undergoes irreversible degradation by membrane-bound S1P lyase, producing (E)-2-Hexadecenal, a derivative of sphingolipid breakdown. This compound can be oxidized to (2E)-hexadecenoic acid by long-chain fatty aldehyde dehydrogenase before being activated through linkage to coenzyme A. Notably, (E)-2-Hexadecenal induces cytoskeletal reorganization, leading to cell rounding, detachment, activation of JNK pathway targets, and ultimate apoptosis in a variety of cell types. Furthermore, it readily forms aldehyde-derived DNA adducts through reactions with deoxyguanosine and DNA.

"(E)-2-Hexadecenal alkyne is a click chemistry probe derivative of the sphingolipid degradation product (E)-2-hexadecenal. This compound has demonstrated the ability to induce cytoskeletal reorganization, leading to cell rounding, detachment, activation of downstream JNK targets, and apoptosis in various cell types. Furthermore, it readily reacts with deoxyguanosine and DNA, forming aldehyde-derived DNA adducts."