Synthesis and Physico‐Chemical Properties of Novel Biocompatible Alkyl<scp>D</scp>‐Mannopyranosiduronate Surfactants Derived from Alginate

Abstract

Abstract 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 α‐ D ‐mannopyranosiduronate) ( 3 ). Double‐tailed amphiphiles were next obtained from this key intermediate 3 by transesterification/transglycosylation 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. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2005)