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Synthesis and comparative study of emulsifying and biological properties of triazolated glucolipids

Year: 2020

Journal: Tetrahedron, Volume 76, OCT 16

Authors: Zhao, Shuang; Zhang, Shixin; Xu, Jintao; Hu, Lei

Organizations: Natural Science Foundation of Jiangsu ProvinceNatural Science Foundation of Jiangsu Province [BK20180853]; China Postdoc Science Foundation [2019M651717]; Six Talent peaks Project in Jiangsu Province [SWYY-162]; senior Talent Program of Jiangsu University [17JDG003]

Keywords: Emulsifier; Glucolipid; Structure-property profiles; Cytotoxicity

Glycolipids represent an attractive type of nonionic emulsifiers (surfactants) due to their abundant renewable resources and good biocompatibility. General preparation methods for glycolipids include enzymatic esterification or Lewis acid-catalyzed glycosylation. In this study, we report the synthesis of a novel series of triazolated alkyl glucolipids as emulsifiers by copper(I)-catalyzed click reactions, with side-chain length ranging from 4 to 10 carbons. The surface-active properties, foaming properties, emulsion properties, thermal stability as well as cytotoxicity of the synthesized compounds are evaluated to establish a comprehensive structure-property profiles, and results suggest the potential utility of medium sized glucolipids in, for example, pharmaceutical and food industries as they show superior performance than the tested commercial references. (C) 2020 Elsevier Ltd. All rights reserved.