Lipase-catalyzed synthesis of ferulate esters

  • David L. Compton
  • Joseph A. Laszlo
  • Mark A. Berhow
Article

Abstract

Four commercially available esterases were screened for their ability to esterify ferulic acid (4-hydroxy-3-methoxy cinnamate). Novozym® 435 was found to be the only one of those screened to convert ferulic acid to ethyl and octyl ferulate at 20 and 14% yields, respectively. The highest percentage conversion was obtained using a 1∶1 mole ratio of alcohol to ferulic acid in stirred batch reactions in anhydrous 2-methyl-2-propanol at 60°C using one equivalent (wt/wt based on ferulic acid) of Novozym 435. Increased water content and a higher alcohol/ethyl ferulate ratio had adverse effects on the lipase-catalyzed esterification. The Novozym 435 activity was tested in less polar solvents (anhydrous toluene and hexane) by monitoring the alcoholysis of ethyl ferulate with 1-octanol, which resulted in a 50% yield of octyl ferulate. The alcoholysis was improved to 83% by applying a 16 mm Hg vacuum for 5 min every 24 h to remove the ethanol co-product. The optimal alcoholysis parameters were applied to the alcoholysis of ethyl ferulate with monoolein and the transesterification with triolein. The transesterification of ethyl ferulate with triolein in anhydrous toluene produced a combined 44% yield of ferulyl monoolein and ferulyl diolein, a 20% greater yield than that obtained for alcoholysis using monoolein. The highest yield, 77%, of ferulyl monoolein and ferulyl diolein was achieved using a threefold excess of neat triolein. The lipase-catalyzed transesterification of ethyl ferulate with triolein appears to be a technically feasible route to ferulyl-substituted acylglycerols, which are potentially useful sunscreen ingredients.

Key Words

Alcoholysis cinnamates ethyl ferulate lipase, monoolein Novozym® 435 transesterification triacylglycerols triolein 

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Copyright information

© AOCS Press 2000

Authors and Affiliations

  • David L. Compton
    • 1
  • Joseph A. Laszlo
    • 1
  • Mark A. Berhow
    • 2
  1. 1.Biomaterials Processing Research UnitUSDA, ARS, NCAURPeoria
  2. 2.Bioactive Agents Research UnitUSDA, ARS, NCAURPeoria

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