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United States Department of Agriculture

Agricultural Research Service

Title: Lipase-Catalyzed Transesterifications and Glycerolysis of Cinnamic Derivatives with Alcohols and Plant Lipids in Unconventional Solvents

item Compton, David
item Laszlo, Joseph
item King, Jerry

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: April 28, 2000
Publication Date: N/A

Technical Abstract: Attempts have been made to synthesize potential sunscreen reagents that may be used in commercial skin care products from plant products and derivatives of plant products. Several commercial lipases were screened to determine which possessed the greatest propensity to catalyze the esterification of cinnamate derivatives. The stirred batch reactions were performed under inert atmospheres in t-butanol and toluene at temperatures between 25 and 60 deg C. Enzyme activity was determined to be dependent on the water content of the reaction with anhydrous conditions affording the greatest enzyme activity, while > 0.5% water (vol/vol) added to the reaction media inhibited enzyme activity. The glycerolysis of the cinnamate derivatives was accomplished under similar anhydrous reaction conditions using mono, di, and triacylglycerols. The glycerolysis reactions afforded up to a 75% yield of cinnamate-derivatized structured lipids, which exhibited broad absorption properties in the UV region. Efforts to conduct similar experiments using supercritical carbon dioxide as the reaction media were also attempted. The lipase-catalyzed glycerolysis of cinnamate derivatives appears to be a technically feasible route to structured lipids that could potentially be used as sunscreen ingredients.

Last Modified: 5/5/2015
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