Experimental and theoretical study of the influence of water on hydrolyzed product formation during the feruloylation of vegetable oil

Authors: Compton, David - Dave; Evans, Kervin; Appell, Michael

Submitted to: Journal of the Science of Food and Agriculture
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 11/15/2016
Publication Date: 12/26/2016
Citation: Compton, D.L., Evans, K.O., Appell, M. 2016. Experimental and theoretical study of the influence of water on hydrolyzed product formation during the feruloylation of vegetable oil. Journal of the Science of Food and Agriculture. 97(9):3022-3029. doi: 10.1002/jsfa.8145.

Interpretive Summary: This research describes the theoretical study of reaction mechanisms that could explain the formation of unwanted side products in the industrial bioreactor process of making soybean oil-based personal care ingredients. Our mission is to develop new, value added, bio-based chemicals and products that replace those made from petroleum and reduce the effects of climate change. The ARS patented technology that attaches a natural plant component, ferulic acid, to soybean oil is being used by industry partners to make soy-based ingredients that absorb UVA and UVB radiation and have antioxidative properties comparable to commercially used petroleum-based ingredients. This research explains the influence of water in the commercial bioreactor processes on the formation of unwanted side products and offers insight into ways to optimize the industrial process and adapting the process to produce a wider variety of commodity vegetable oil-based products. Agricultural research to support the development of value-added, commodity oil-based commercial products is an essential component of establishing a bio-based economy to combat climate change and expand markets for agricultural producers.

Technical Abstract: Feruloylated vegetable oil is a valuable green bioproduct that has several cosmeceutical applications associated with its inherent anti-oxidant and UV-absorption properties. Hydrolyzed vegetable oil by-products can influence product quality and consistency. The formation of by-products by residual water in the enzymatic synthesis of feruloylated vegetable oil was investigated using chemical theory and experimental studies by monitoring the reaction over a 22 day period. The hydrolysis of vegetable oil is thermodynamically favored over the hydrolysis of the ethyl ferulate starting material. These results suggest that hydrolyzed vegetable oil products will be experimentally observed in greater concentrations compared to hydrolyzed ethyl ferulate products. The quantum chemical studies identified several reaction mechanisms that explain the formation of side products by water, suggesting residual water influences product quality. Efforts to reduce residual water can improve product consistency and reduce purification costs.