Esterification of Fructose-oleic Acid by tert-Butanol/Dimethyl Sulfoxide and by 2-Methyl-2-butanol/Dimethyl Sulfoxide

J Oleo Sci. 2020 Oct 7;69(10):1281-1285. doi: 10.5650/jos.ess20142. Epub 2020 Sep 10.

Abstract

In this study two different strategy were followed to obtain a D-fructose-oleic acid ester. One of the strategies has been well established enzymatic synthesis of an ester bond. The other strategy excluded the biocatalyst and only used a mixture of two organic solvents as the reaction media, 2-methyl-2-butanol / dimethyl sulfoxide or tert-butanol / dimethyl sulfoxide for the production of D-fructose-oleic acid ester. Ester products obtained were characterised by using FT-IR, NMR, by MS. Product yield was also assessed by HPLC. Results of structural analyses and yield measurement indicated that two approaches produced almost identical ester products.

Keywords: 2-methyl-2-butanol; dimethyl sulfoxide; fructose; oleic acid; sugar-fatty acid esterification; tert-butanol.

MeSH terms

  • Animals
  • Biocatalysis
  • Cells, Cultured
  • Chromatography, High Pressure Liquid
  • Dimethyl Sulfoxide / chemistry*
  • Esterification
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Esters / toxicity
  • Fructose / chemical synthesis*
  • Fructose / chemistry
  • Fructose / toxicity
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Oleic Acid / chemical synthesis*
  • Oleic Acid / chemistry
  • Oleic Acid / toxicity
  • Pentanols / chemistry*
  • Spectroscopy, Fourier Transform Infrared
  • tert-Butyl Alcohol / chemistry*

Substances

  • Esters
  • Pentanols
  • Oleic Acid
  • Fructose
  • tert-amyl alcohol
  • tert-Butyl Alcohol
  • Dimethyl Sulfoxide