Novel Pseudoceramides And Their Synthesis Using Alkyl Ketene Dimer

Nowadays, ceramides have been found to be an important component in the outermost layer of the skin - the stratum corneum. It is undersrood that ceramides play an important role in structure and maintenance of the interellular lipid lamella structure in the SC layer. Thus, many efforts have been made by the cosmetics and pharmaceutical industries to get human skin-identical ceramides or pseudoceramides which show similar performance with natural ceramides. The purpose of our study was to systhesize new pseudoceramides via an effective and economical systhetic pathway and to show their performance of skin restoratio. Four kinds of the new pseudoceramides were synthesized by the reaction of alcoholic amine and alkyl ketene dimer. First of all, PC-4 and PC-5 were synthesized by the reaction of 3-amino-1,2-propanidiol and serinol with alkyl ketene dimer respectively. After that, PC-4R and PC-5R were produced by changign kitone group at $\beta$-position to amide bond of above synthesized PC-4 and PC-5 into hydroxyl group using NaBH4 respectively. Their expected structures were conformed by the NMR, IR spectra, and elemental analysis. A study to show the restoration effectiveness was performed in which human skin was pretreated with high concentration of SDS surfactant solution. Using 0.5% solution of above synthesized pseudoceramides, there was the significantly faster restoration of the damaged than that of placebe itself treatment.