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Ethyl ferulate was transesterified with Enova Oil (a soy-based vegetable oil containing 80&#8722;85% diacylglycerol) using Novozym 435 at 60 &#176;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-<i>sn</i>-glycerol (F₂G) and 1-feruloyl-<i>sn</i>-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, and 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 &#177; 0.052 g, 39.6 &#177; 1.7%) and FG (0.313 &#177; 0.038 g, 10.4 &#177; 1.3%) from 3.0 g of the transesterification precipitate, <i>n</i> = 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 process ~100 g of material in a timely, efficient manner.