Synthesis of fatty alcohol esters of alpha-hydroxy carboxylic acids and their use as percutaneous absorption enhancers

摘要

The present invention provides a novel approach for the preparation of fatty alcohol esters of α-hydroxy carboxylic acids. In one form of the invention, the target fatty alcohol ester of α-hydroxy carboxylic acid is produced by converting a lower alkyl ester of α-hydroxy carboxylic acid into a fatty alcohol ester of α-hydroxy carboxylic acid via alcoholysis (i.e., transesterification). The transesterification process is an equilibrium reaction, catalyzed chemically (i.e., with acids or bases) or enzymatically, that is shifted in the desired direction to produce the desired product. One way of shifting the reaction in the direction of the desired product is by reducing the concentration of one of the products (e.g., distillation of a lower-boiling alcohol as it is formed). Another preferred way of shifting the reaction in the direction of the desired product is by increasing the concentration of one of the reactants.

主权项

1. A method for synthesizing a fatty alcohol ester of α-hydroxy carboxylic acid, comprising:
converting a lower alkyl ester of α-hydroxy carboxylic acid into a fatty alcohol ester of α-hydroxy carboxylic acid via transesterification, wherein the transesterification process is an equilibrium reaction that is shifted in the desired direction to produce the desired product by reducing the concentration of one of the products of the transesterification process; wherein one of the products of the transesterification process is an alcohol, and further wherein the concentration of that alcohol is reduced by distillation.