Synthesis of water-soluble retinol derivatives by enzymatic method.
Retinoids (vitamin A and derivatives) are of great commercial potential in cosmetics and pharmaceuticals such as skin care products. However, the clinical effectiveness of these retinoids is limited by skin irritation, water insolubility, and except for retinyl-esters, extreme instability. In this paper, an enzymatic method for preparing water-soluble retinol derivatives catalyzed by immobilized lipase is described. The synthesis is based on a unique strategy of two-step enzymatic acylation. Among the different synthesized compounds, the most water-soluble are the disaccharide derivatives such as saccharose retinyl adipate (nonionic water-soluble retinol derivative) and the sodium salt of retinyl diacids such as retinyl succinate sodium salt (ionic water-soluble retinol derivative).
Maugard
Thierry
T
Laboratoire de Génie Protéique et Cellulaire, EA3169, Université de La Rochelle, Avenue Michel Crépeau, 17042 La Rochelle Cedex 1, France. tmaugard@univ-lr.fr
Rejasse
Barbara
B
Legoy
Marie Dominique
MD
D002175:Candida / Q000201:enzymology; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D004800:Enzymes, Immobilized / Q000378:metabolism; D008049:Lipase / Q000378:metabolism; D012995:Solubility; D013056:Spectrophotometry, Ultraviolet; D014801:Vitamin A / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D014867:Water
D004800:Enzymes, Immobilized; D014867:Water; D014801:Vitamin A; D008049:Lipase