Glycolipid surfactants, comprised of sugar headgroups and lipid tails, offer high biodegradability and low toxicity while maintaining excellent surfactant performance. Their potential as greener alternatives to commonly used surfactants requires systematic study of the structure-function relationship of various glycolipid surfactants. This type of study has been precluded previously by costly and difficult synthesis; however, recent advancements in facile synthesis of highly pure glycolipid surfactants enable the analysis of a diverse set of glycolipids. This paper investigates the solution phase properties of two suites of glycolipid surfactants, O-n-alkylmelibiosides and O-n-alkylcellobiosides, which are composed of melibiose or cellobiose headgroups and varying straight-chain alkyl tails of 8-12 carbons. Surface tensiometry shows CMC values of 0.1-40 mM and molecular areas of 48-70 Å<sup>2</sup>/molecule. Dynamic light scattering documents multiple aggregate populations with a predominant micelle population of R<sub>h</sub> ~2 nm with an aggregation number of 50-100 molecules/micelle determined by fluorescence spectroscopy. The comparatively larger headgroup size of melibiose and greater hydrophobicity and tail length of longer alkyl chains greatly affect the principal surfactant properties.

Properties of novel bioinspired glycolipid surfactants: Tailoring function by disaccharide headgroup and alkyl tail length

249th National Meeting (2015)

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