Fatty acid ester surfactants derived from raffinose: Synthesis, characterization and structure-property profiles

Abstract

Hypothesis: The development of functional and nutritional surfactants for the food industry remains a subject of great interest. Herein, therefore, we report on the design and synthesis of novel trisaccharide (raffinose) monoester-based surfactants in the expectation that they would display functional properties superior to certain disaccharide-based, commercially-deployed emulsifiers and thus have potential for industrial applications. Experiments: The title esters were prepared by enzymatic methods and their properties as surfactants evaluated through determination of their HLB values, water solubilities, CMCs, foamabilities and foaming stabilities as well as through investigation of their impacts on the stability of oil-in-water emulsions over a range of storage times and under certain other conditions. Findings: The emulsifying properties of 6-O-acylraffinose esters are dictated, in large part, by the length of the associated alkyl chains. The results of storage and environmental stress experiments revealed that the increasing length of alkyl chains enhances the stability of the derived emulsions. All the raffinose ester-stabilized oil-in-water emulsions displayed stratification effects under strongly acidic conditions (pH 4) or at high ionic strength (!300 mM) while possessing reasonable resistance to variations in

Emulsifying Properties of an Homologous Series of Medium- and Long-Chain d-Maltotriose Esters and their Impacts on the Viabilities of Selected Cell Lines

“…Specifically, after treating the cells with 150 μM ester 6 , the level of cyclin D1 decreased by 80%, while that of cyclin E fell by 40%. It is known that cyclin-dependent kinase 2 (CDK 2) combines with cyclin E, while CDK4 combines with cyclin D1 to form complexes that accompany the G1-S phase progression of cells. − As such, ester 6 must decrease the level of CDK4 preferentially over that of CDK2. Overall, then, the observed G1 phase arrest in MCF-7 breast cancer cells by compound 6 occurs via simultaneous downregulation of cyclin E, cyclin D1, and CDK4.…”

Efficient Acylation of Sugars and Oligosaccharides in Aqueous Environment Using Engineered Acyltransferases

“…As shown by thin layer chromatography–mass spectrometry (TLC-MS), wild-type EstCE1 could also catalyze the monoacetylation of maltose and maltotriose (Figure S8). Esters of oligosaccharides have significant potential for applications as, for example, emulsifiers . By comparing wild-type EstCE1 and EstCE1-MAA in reactions of ethyl acetate with glucose/maltose/maltotriose, we observed that EstCE1-MAA outperformed the wild type for all three sugars (Figure ).…”

Enzymatic Methods for the Manipulation and Valorization of Soapstock from Vegetable Oil Refining Processes

“…The use of soapstock as a source of FFAs for the synthesis of fine chemicals is to be further investigated to expand the variety of products that can be obtained. The possibility to prepare other biodegradable surfactants [83], monomers for bio-based biodegradable new-generation polymers [84,85], and additives for the cosmetic industry [86][87][88] has to be carefully investigated.…”