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 (96.4 g, 4.02 wt%) after 7 d 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 ± 0.052 g, 39.6 ± 1.7 %) and FG (0.313 ± 0.038 g, 10.4 ± 1.3 %) from 3.0 g of the transesterification precipitate, n = 10 trials. Overall, all flash chromatography separations combined, F2G (39.1 g, 40.6 %) and FG (9.4 g, 9.8 %) were isolated in a combined yield of 48.5 g (51.4 %), relative to the 96.4 g 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 ~ 100 g of material in a timely, efficient manner.

Production and purification of natural phenylpropenoids

ACS Spring Meeting 2021

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