Isosorbide as a novel polar head derived from renewable resources. Application to the design of short-chain amphiphiles with hydrotropic properties

Abstract

The potential use of isosorbide, an original diol readily obtained by the double dehydration of sorbitol, has been investigated for the synthesis of novel amphiphilic species. The hydrophilicity of this polar head has been assessed via the synthesis and evaluation of three short-chain monoalkyl derivatives. The isosorbide polar head appears to have an unexpectedly low hydrophilicity, comparable to a diethylene oxide unit and it exhibits similar sensitivity to temperature changes. The monobutyl and monopentyl ethers of isosorbide have been found to be very efficient for the solubilisation of a model hydrophobic compound in water, giving promising hints on the use of isosorbide for the design of hydrotropic compounds.