Enzymatic synthesis and application of fatty acid ascorbyl esters

Abstract

Fatty acid ascorbyl esters are liposoluble substances that possess good antioxidative properties. These compounds could be synthesized by using various acyl donors for acylation of vitamin C in reaction catalyzed by chemical means or lipases. The enzymatic process is preferred since it is regioselective, performed under mild reaction conditions, with the obtained product being environmentally friendly. Polar organic solvents, ionic liquids, and supercritical fluids have been successfully used as a reaction media, since commonly used solvents with high log P values are inapplicable due to ascorbic acid high polarity. Acylation of vitamin C using fatty acids, their methyl-, ethyl-, and vinyl esters, as well as triglycerides has been performed, whereas application of the activated acyl donors enabled higher molar conversions. In each case, the majority of authors reported that using excessive amount of the acyl donor had positive effect on yield of product. Furthermore, several strategies have been employed for shifting the equilibrium towards the product by water content control. These include adjusting the initial water activity by pre-equilibration of reaction mixture, enzyme preparation with water vapor of saturated salt solutions, and the removal of formed water by the addition of molecular sieves or salt hydrate pairs. The aim of this article is to provide a brief overview of the procedures described so far for the lipase-catalyzed synthesis of fatty acid ascorbyl esters with emphasis on the potential application in food, cosmetics, and pharmaceutics. Furthermore, it has been pointed out that the main obstacles for process commercialization are long reaction times, lack of adequate purification methods, and high costs of lipases. Thus, future challenges in this area are testing new catalysts, developing continuous processes for esters production, finding cheaper acyl donors and reaction mediums, as well as identifying standard procedures for purification of products which will not require consumption of large amounts of non-biocompatible organic solvents.

Askorbil-estri masnih kiselina su liposolubilna antioksidativna jedinjenja koja se pod blagim reakcionim uslovima mogu dobiti u reakcijama acilovanja vitamina C pomoću lipaza. Kao reakcione sredine do sada su bili uspešno korišćeni polarni organski rastvarači, jonske tečnosti i natkritični fluidi. Na ravnotežnu konverziju, pozitivan efekat pokazala je kontrola sadržaja vode kao i upotreba aktiviranih acil donora, a negativan efekat je poskupljenje i/ili smanjenje produktivnosti procesa. U ovom radu prikazan je kratak pregled do sada opisanih postupaka enzimske sinteze askorbil-estara masnih kiselina sa navođenjem njihove potencijalne primene kao aditiva u prehrambenoj, kozmetičkoj i farmaceutskoj industriji.