Alkyl glycosides and polyglycosides

Surface Activity and Critical Aggregation Concentration of Pure Sugar Esters with Different Sugar Headgroups

“…In addition, the possibility of the existence of charged impurities in the surfactant sample (e.g., fatty acids) is therefore also unlikely. Work done on alkyl glucosides, however, has shown a dependency of the cloud point of these surfactants on the salt concentration (43,44). This has been attributed to the presence of a low number of charges on the surfactant molecules.…”

Synthesis, preliminary characterization, and application of novel surfactants from highly branched xyloglucan oligosaccharides

“…Furthermore, carbohydrates are attractive starting materials for chemical elaboration due to their status as a renewable resource (Holmberg, 2001;Von Rybinski, 1996). When conjugated with fatty acids, long-chain alkanols, or other natural hydrophobic species (Johansson and Svensson, 2001;Piispanen et al, 2002), the resulting compounds are appealing alternatives to surfactants of petrochemical origin.…”

“…When conjugated with fatty acids, long-chain alkanols, or other natural hydrophobic species (Johansson and Svensson, 2001;Piispanen et al, 2002), the resulting compounds are appealing alternatives to surfactants of petrochemical origin. In particular, the alkylglycosides find widespread use in the food, hygiene, and cosmetics industries (Biermann et al, 1993;Hill and Rhode, 1999;Von Rybinski, 1996), as well as in research applications, such as membrane protein extraction (Garavito and Ferguson-Miller, 2001;Jones, 1999;Le Maire et al, 2000), due to their biological compatibility.…”

“…The diversity of reactions that can be used to modify the polyhydroxylated sugar ring, as well as the ability to control the regio-and stereoselectivity of those reactions, has resulted in the synthesis of a tremendous range of carbohydrate-based surfactants based on glucose alone (Augé and Lubin-Germain, 2000;Stubenrauch, 2001). Indeed, the industrial synthesis of octyl-glucoside, which is carried out using specific acid catalysis, gives rise to a mixture of glucose derivatives: glucosides of both anomeric configurations, α and β, as well as longer octyl-glucooligosaccharides with mixed sugar linkages (Von Rybinski, 1996), each of which possesses unique surfactant properties (Persson et al, 2000).…”

Interglycolipid Membrane Interactions: pH-Dependent Aggregation of Nonionic Synthetic Glycolipid Vesicles

“…Glycolipids are one of the major components of cell membranes and are believed to be involved in variety of physiological events (1, 2) such as molecular recognition at cell surfaces (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12). From a technical view point, glycolipids synthesized from renewable resources, like oligosaccharides and fatty alcohol, are less environmentally damaging than many other synthetic surfactants (13,14). Moreover, possible biological functions involved in certain oligosaccharide headgroups may make glycolipids particularly attractive as a new type of lipids for liposomal drug delivery systems (15) and various aspects of biotechnology (16).…”