Production and purification of natural phenylpropenoids

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

Submitted to: American Chemical Society National Meeting
Publication Type: Abstract Only
Publication Acceptance Date: 3/11/2021
Publication Date: 4/13/2021
Citation: Compton, D.L., Appell, M.D., Kenar, J.A., Evans, K.O. 2021. Production and purification of natural phenylpropenoids. [abstract]. American Chemical Society. Virtual Meeting. Paper No. 3551779.

Interpretive Summary:

Technical Abstract: Ethyl ferulate was transesterified with a soy-based vegetable oil containing 80 – 85% diacylglycerol using Novozym 435 at 60°C. The resultant feruloylated vegetable oil reaction product produced a precipitate (96.4g, 4.02wt.%) after 7d of standing at room temperature. Preliminary characterization of the precipitate identified the natural phenylpropenoids 1,3-Diferuloyl-sn-glycerol (F2G) and 1-Feruloyl-sn-glycerol (FG) as the major components. A flash chromatography method was developed and optimized (e.g., mass of sample load, flow rate, binary solvent gradient slope, separation run length) using a binary gradient of hexane and acetone mobile phase and silica gel stationary phase to separate and isolate F2G and FG. The optimized parameters afforded F2G (1.188 ± 0.052g, 39.6 ± 1.7%) and FG (0.313 ± 0.038g, 10.4 ± 1.3%) from 3.0g of the transesterification precipitate, n = 10 trials. Overall, all flash chromatography separations combined, F2G (39.1 g, 40.6%) and FG (9.4g, 9.8%) were isolated in a combined yield of 48.5g (51.4%), relative to the 96.4g of transesterification precipitate collected. The optimized flash chromatography method was a necessary improvement over previously reported preparative HPLC and column chromatography methods used to purify milligram to low gram quantities of F2G and FG to be able to processes ~ 100g of material in a timely, efficient manner.