Submitted to: Soybean Research World Conference Proceedings
Publication Type: Proceedings
Publication Acceptance Date: August 10, 2009
Publication Date: August 15, 2009
Citation: Compton, D.L., Laszlo, J.A. 2009. Biocatalytic refining of soybean oil into cosmeceutical ingredients. Proceedings of Soybean Research World Conference. CD G5-005. Interpretive Summary: Our group has developed and patented a soybean oil based sunscreen, antioxidant ingredient, called Feruloyl Soy Glycerides (FSG), which is now being used in several commercial retail products available from Elizabeth Arden and Peter Thomas Roth cosmetic companies. Efforts to assist our commercial partners to improve production methods and capacities have led to the discovery of an additional all-natural product that could be used by the cosmetic industry. Feruloyl glycerol is a byproduct from the patented FSG manufacturing process that can be easily isolated from the FSG product. Feruloyl glycerol has good sunscreen and antioxidant properties and, unlike FSG, is more water soluble. This research could lead to a range of new water-based cosmetic products. The current research fulfills our congressional mission to develop new, value-added uses for agricultural products and transfer the new technologies to the market place.
Technical Abstract: Our mission is to develop new, value-added uses for commodity crops and oils. We chose to fulfill this mission while adhering as closely as possible to the tenants of “green” chemistry. We have developed patented, all-natural oils called Feruloyl Soy Glycerols (FSG) from the biocatalytic transesterification of soybean oil and ferulic acid ethyl ester (ethyl ferulate). FSG is currently being used as an ultraviolet (UV) absorbing and antioxidant ingredient in several retail skin care formulations. FSG is produced on a pilot plant scale by passing solutions of ethyl ferulate dissolved in soybean oil—no other solvent is employed—at 60°C over packed-bed columns of a commercial, immobilized lipase. The solution is slowly converted to FSG over days and is harvested after >50% conversion and requires no additional purification. Current capacity allows for the production of several metric tons of FSG per year. The rate of FSG production was significantly increased using mono- and diacylglycerols from soybean oil instead of soybean oil. Partially deacylating the soybean oil via lipase-catalyzed propanolysis or glycerolysis prior to the transesterification with ethyl ferulate results in >50% conversion to FSG within 24 h. The higher water content of the modified process, due to the greater hygroscopic nature of the mono- and diacylglycerols, resulted in the formation of significant quantities of diferuloyl glycerol, which contain no fatty acid moieties, in ~4% yield. The white solid was easily collected by filtration from the FSG and provides a more hydrophilic alternative to FSG.