Synthesis and properties of natural occurring α-hydroxyaldehydes

Article abstract of DOI:10.1016/0040-4020(96)00089-0

A synthesis for aliphatic α-acetoxyaldehydes 18 is presented. These were converted to free aldehydes 9 by action of hog liver esterase. Aliphatic α-hydroxyaldehydes, recently recognized to be produced in the course of lipid-peroxidation of linoleic and other unsaturated fatty acids, are only stable for short time in solution. They react with amines to give Schiff bases. These are instable, but can be trapped after reduction with NaBH₄ to the corresponding amines. Since α-hydroxyaldehydes are produced in the case of lipid peroxidation and were found to stimulate oxidative stress, Schiff base formation might be a physiological important process. α-Hydroxyaldehydes form under physiological conditions mercaptals by reaction with thiols.