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

S.E.H.J. van Kempen, C.G. Boeriu, H.A. Schols, P. de Waard, E. van der Linden, L.M.C. Sagis

Research output: Contribution to journalArticleAcademicpeer-review

39 Citations (Scopus)

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/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.
Original languageEnglish
Pages (from-to)1884-1891
JournalFood Chemistry
Volume138
Issue number2-3
DOIs
Publication statusPublished - 2013

Keywords

  • lipase-catalyzed synthesis
  • candida-antarctica lipase
  • solid-phase synthesis
  • regioselective acylation
  • fructose esters
  • chain-length
  • disaccharides
  • inulin
  • oligosaccharides
  • ingredients

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