Highly Efficient Synthesis of an Emerging Lipophilic Antioxidant: 2-Ethylhexyl Ferulate

Molecules. 2016 Apr 12;21(4):478. doi: 10.3390/molecules21040478.

Abstract

Ferulic acid in ester form has shown a stronger ability in ameliorating certain pathological conditions and inhibiting lipid oxidation. In present study, a solvent-free and reduced pressure evaporation system was developed for lipase-catalyzed synthesis of 2-ethylhexyl ferulate (2-EF) from ferulic acid and 2-ethylhexanol. A Box-Behnken design with response surface methodology (RSM) and artificial neural network (ANN) was selected to model and optimize the process. Based on the yields of 2-EF, reaction temperature was shown to be the most important process factor on the molar conversion among all variables. The residual values and the coefficient of determination (R²) calculated from the design data indicated that ANN was better than RSM in data fitting. Overall, the present lipase-catalyzed approach for 2-EF synthesis at low reaction temperature in a reduced pressure evaporation system shows high 2-EF production efficiency. Notably, this approach can reduce the enzyme denaturation and ferulic acid oxidation that usually occur during long-term biosynthetic operations at high temperature.

Keywords: 2-ethylhexyl ferulate; artificial neural network; lipase; reduced pressure evaporation system; response surface methodology.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Coumaric Acids / chemical synthesis*
  • Coumaric Acids / chemistry
  • Esters / chemical synthesis
  • Hexanols / chemistry*
  • Lipase / chemistry
  • Lipid Peroxidation / drug effects
  • Neural Networks, Computer
  • Solvents / chemistry

Substances

  • Antioxidants
  • Coumaric Acids
  • Esters
  • Hexanols
  • Solvents
  • ferulic acid
  • Lipase
  • 2-ethylhexanol