1,3-Diferuloyl-sn-glycerol from the biocatalytic transesterification of ethyl 4-hydroxy-3-methoxy cinnamic acid (ethyl ferulate) and soybean oil

Authors: Compton, David - Dave; Laszlo, Joseph

Submitted to: Biotechnology Letters
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/6/2009
Publication Date: 6/1/2009
Citation: Compton, D.L., Laszlo, J.A. 2009. 1,3-Diferuloyl-sn-glycerol from the biocatalytic transesterification of ethyl 4-hydroxy-3-methoxy cinnamic acid (ethyl ferulate) and soybean oil. Biotechnology Letters. 31(6):889-896.

Interpretive Summary: This research resulted in the discovery of another all-natural product that could lead to the development of new products by the cosmetic industry. Previously our team developed and patented a soybean oil based sunscreen, antioxidant ingredient called Feruloyl Soy Glycerides (FSG). FSG 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, it 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: 1,3-Diferuloyl-sn-glycerol is a natural plant component found ubiquitously throughout the plant kingdom, possessing ultraviolet adsorbing and antioxidant properties. Diferuloyl glycerol was synthesized and isolated as a byproduct in up to 5% yield from the pilot plant scale packed-bed, biocatalytic transesterification of ethyl ferulate with soybean oil or mono- and diacylglycerols from soybean oil. The yield of the diferuloyl glycerol byproduct was demonstrated to be directly proportional to the overall water activity of the bioreactor. The isolated diferuloyl glycerol exhibited good ultraviolet adsorbing properties, 280 to 360 nm with a lambda max 322 nm, and compared well to the efficacy of commercial sunscreen active ingredients. The antioxidant capacity of diferuloyl glycerol (0.25 to 2.50 mM) was determined by its ability to scavenge 2,2-diphenyl-1-picrylhydrazyl radicals and was found comparable to that of ferulic acid. At current pilot plant scale production capacity, 120 kg of diferuloyl glycerol byproduct could be isolated per year.