Synthesis and physico-chemical properties of novel biocompatible alkyl D-mannopyranosiduronate surfactants derived from alginate

The present article describes the preparation and the physico-chemical properties of novel biocompatible surfactants derived from alginate for applications in detergents and cosmetics. Controlled acid hydrolysis of commercially available alginate from Laminaria digitata gives saturated oligo-mannuronates on a multigram scale. Subsequent one-pot acid glycosidic bond hydrolysis, esterification and stereocontrolled Fischer glycosylation in butanol with the related oligouronates efficiently provides n-butyl (n-butyl alpha-D-manno-pyranosiduronate) (3). Double-tailed amphiphiles were next obtained from this key intermediate 3 by transesterification/ trans glycosylation processes in fatty alcohols. Aqueous basic and acid treatments furnished anionic or neutral single-tailed surfactants. These original alginate-derived amphiphiles exhibit attractive surface-tension and foaming properties. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.