Alkyl xyloside are of interest as biodegradable surfactants that can be prepared from renewable sources, such as hemicelluloses. In this work, we investigated the effect of linking the alkyl chain to the xyloside with a 1,2,3-triazole linker. The final products were characterized by differential scanning calorimetry (DSC), in vitro toxicology assays and Langmuir monolayer analysis. Their melting points were correlated with hydrocarbon chain length; unlike simple alkyl xylosides, the triazole-containing surfactants did not exhibit any characteristics of liquid crystals. Biocompatibility was assessed in vitro in several cell lines; only the compounds with intermediate-length chains exhibited toxicity. The triazole-linked surfactants were surface-active and formed stable monolayers at the air-water interface. Thus, we have identified a series of novel, triazole-linked alkyl xylosides with biological and physicochemical properties that are distinctively different from simple alkyl xylosides. These compounds are of potential interest for consumer and industrial applications.

Synthesis and characterization of triazole-containing alkyl xyloside surfactants

244th National Meeting (2012)

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