Novel surface-active oligofructose fatty acid mono-esters by enzymatic esterification

• Published in: Food chemistry Vol. 138; no. 2-3; pp. 1884 - 1891
• Main Authors: van Kempen, Silvia E.H.J., Boeriu, Carmen G., Schols, Henk A., de Waard, Pieter, van der Linden, Erik, Sagis, Leonard M.C.
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 01.06.2013; Elsevier
• Subjects: Biological and medical sciences; Candida - enzymology; Enzymatic esterification; Esterification; Esters - chemistry; Fatty acid chain length; Fatty Acids - chemistry; Food industries; Food-grade surfactant; Fundamental and applied biological sciences. Psychology; Fungal Proteins - chemistry; Lipase; Lipase - chemistry; Molecular Structure; Oligofructose; Oligosaccharides - chemistry; Surface-Active Agents - chemical synthesis; Surface-Active Agents - chemistry; Fatty acid chain length; Food-grade surfactant; Lipase; Enzymatic esterification; Oligofructose; Enzyme; Chain length; Fatty ester; Triacylglycerol lipase; Lipids; Esterases; Surfactant; Fatty acids; Esterification; Carboxylic ester hydrolases; Surface; Hydrolases; Dietary fiber; Food; Enzymatic reaction
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2012.09.133

► Lipase catalysed esterification of oligofructose with different fatty acids. ► Mono-esters were the main reaction products. ► Pure products were obtained by reverse phase solid phase extraction. ► Esters of longer fatty acids had better surface properties. This article describes the synthesis of a series of oligofructose monoesters with fatty acids of different chain length (C8, C12, C16 and C18) to obtain food-grade surfactants with a range of amphiphilicity. Reactions were performed in a mixture of DMSO/ButOH (10/90 v/v) at 60°C and catalysed by immobilised Candida antarctica lipase B. MALDI-TOF-MS analysis showed that the crude reaction products were mixtures of unmodified oligofructose and mostly mono-esters. The conversion into mono-esters increased with the length of the fatty acid chain, reflecting the specificity of the lipase towards more lipophilic substrates. Reverse phase solid phase extraction was used to fractionate the products, which lead to sufficient purity (>93%) of the fatty acid esters for functionality testing. It was shown that derivatives of longer (C16 and C18) fatty acids were more efficient in lowering surface tension and gave a much higher dilatational modulus than derivatives of the shorter (C8 and C12) fatty acids.