Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/25/2006
Publication Date: 9/1/2006
Citation: Compton, D.L., Laszlo, J.A., Berhow, M.A. 2006. Identification and quantification of feruloylated mono-, di-, and triacylglycerols from vegetable oils. Journal of the American Oil Chemists' Society 83(9):753-758.
Interpretive Summary: The goal of our project is to develop new, environmentally benign methods to help convert a portion of the 800,000 lbs of excess soybean oil produced in the U.S. to new, value-added uses, such as nutritional, industrial, and cosmetic ingredients. We have developed a new, patented material that we make from the combination of soybean oil and ferulic acid, a compound of the cinnamon family, found in plants. The ferulic acid portion absorbs ultraviolet (UV) A and B radiation while the oil portion is water insoluble. These characteristics make the new material, SoyScreen(TM), an ideal all natural replacement for petroleum-based UVA and UVB absorbers currently used in sunscreens, cosmetics, agricultural sprays, and other industrial uses such as paints and coatings. The work done in this study improves the analytical methods used to identify and quantify the amount of SoyScreen(TM) made during our "green," biocatalytic process. These new analytical methods will be used by industrial partners that have licensed the SoyScreen(TM) technology from the USDA to set and monitor quality control standards during SoyScreen(TM) production and process improvements.
Technical Abstract: The use of high performance liquid chromatography-mass spectroscopy (HPLC-MS) to separate and identify the feruloylated acylglycerols formed during the transesterification of ethyl ferulate with triacylglycerols was examined. The transesterifications were catalyzed by Candida antartica lipase B. The feruloylated acylglycerols were separated by HPLC using a phenyl-hexyl reverse phase column developed with a water/methanol gradient. MS was used to successfully identify the feruloyl oleoylglycerol species formed during the transesterification of triolein with ethyl ferulate. The distribution of hydrolysis products from the reaction of the feruloylated oleoylglycerols with excess water catalyzed by Burkholderia cepacia, which showed no reactivity towards the feruloyl moiety, allowed for the assignment of the feruloyl oleoylglycerol positional isomers.