Spectroscopic and theoretical evaluation of feruloyl derivatives: Insights into their electronic properties

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

Submitted to: Results in Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 3/26/2025
Publication Date: 4/2/2025
Citation: Evans, K.O., Compton, D.L., Appell, M.D. 2025. Spectroscopic and theoretical evaluation of feruloyl derivatives: Insights into their electronic properties. Results in Chemistry. https://doi.org/10.1016/j.rechem.2025.102225.
DOI: https://doi.org/10.1016/j.rechem.2025.102225

Interpretive Summary: ARS researchers in Peoria, Illinois, developed technology to attach vegetable oils (e.g., soybean, coconut) to a natural plant compound, called ferulic acid, that has ultraviolet blocking and antioxidant properties. These unique modified oils are produced commercially for cosmetic applications requiring SPF boosting or protecting UV-sensitive ingredients like vitamins C or E. During the manufacturing process, there are several products and byproducts in the reaction mix that are difficult to quantify. Having the ability to quickly determine the concentration of these compounds allows scientists to assess the efficiency of the conversion so that adjustments can be made to push the reaction towards the final product. In this study, ARS researchers developed a detection technique to easily quantify the reaction products involved in the manufacturing process. This work advances the development of rapid detection methods for similar modified vegetable oils and facilitates further product innovation using ARS technology.

Technical Abstract: he spectroscopic characterization of ferulic acid (FA), ethyl ferulate (EF), 1-feruloyl-glycerol (FG), and 1,3-diferuloyl-glycerol (DFG) was done using absorbance spectrophotometry and fluorescence excitation-emission matrix (EEM) analysis. Absorbance measurements demonstrated that each feruloyl derivative (FA, EF, FG, and DFG) existed in two forms in water at pH 4.6, a fully neutral form (X, X = FA, EF, FG, or DFG) and a mono-deprotonated form (X-). Absorbance and EEM analysis indicated that the primary path of excitation to emission were through the ground state S0 of the neutral forms to the first excited state S1 for the mono-deprotonated forms of FA, EF, FG, and DFG (FA-, EF-, FG-, and DFG-).