title: Novel surface-active oligofructose fatty acid mono-esters by enzymatic esterification.
abstract: 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/Bu(t)OH (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.
authors: Laboratory of Physics and Physical Chemistry of Foods, Wageningen University and Research Center, Bomenweg 2, 6703 HD Wageningen, The Netherlands.
authors: Silvia E H J
authors: SE
authors: van Kempen
authors: Carmen G
authors: CG
authors: Boeriu
authors: Henk A
authors: HA
authors: Schols
authors: Pieter
authors: P
authors: de Waard
authors: Erik
authors: E
authors: van der Linden
authors: Leonard M C
authors: LM
authors: Sagis
mesh_terms: D002175:Candida / Q000201:enzymology*; D004951:Esterification; D004952:Esters / Q000737:chemistry*; D005227:Fatty Acids / Q000737:chemistry*; D005656:Fungal Proteins / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry*; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D004952:Esters; D005227:Fatty Acids; D005656:Fungal Proteins; D009844:Oligosaccharides; D013501:Surface-Active Agents; C120489:oligofructose; D008049:Lipase