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Enzymatic Synthesis and Flash Chromatography Separation of 1,3-Diferuloyl-sn-Glycerol and 1-Feruloyl-sn-Glycerol

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Renewable Product Technology Research Unit, United States Department of Agriculture, Agricultural Research Service, National Center for Agricultural Utilization Research, 1815 N. University Street, Peoria, IL 61604, USA
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Mycotoxin Prevention and Applied Microbiology, United States Department of Agriculture, Agricultural Research Service, National Center for Agricultural Utilization Research, 1815 N. University Street, Peoria, IL 61604, USA
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Functional Foods Research Unit, United States Department of Agriculture, Agricultural Research Service, National Center for Agricultural Utilization Research, 1815 N. University St., Peoria, IL 61604, USA
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Author to whom correspondence should be addressed.
Mention of trade names or commercial products in this publication is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the United States Department of Agriculture (USDA). USDA is an equal opportunity provider and employer.
Methods Protoc. 2020, 3(1), 8; https://doi.org/10.3390/mps3010008
Received: 20 November 2019 / Revised: 9 January 2020 / Accepted: 14 January 2020 / Published: 16 January 2020
Ethyl ferulate was transesterified with Enova Oil (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, 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 ± 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 process ~100 g of material in a timely, efficient manner. View Full-Text
Keywords: diferuloyl glycerol; feruloyl glycerol; flash chromatography; transesterification diferuloyl glycerol; feruloyl glycerol; flash chromatography; transesterification
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MDPI and ACS Style

Compton, D.L.; Appell, M.; Kenar, J.A.; Evans, K.O. Enzymatic Synthesis and Flash Chromatography Separation of 1,3-Diferuloyl-sn-Glycerol and 1-Feruloyl-sn-Glycerol. Methods Protoc. 2020, 3, 8. https://doi.org/10.3390/mps3010008

AMA Style

Compton DL, Appell M, Kenar JA, Evans KO. Enzymatic Synthesis and Flash Chromatography Separation of 1,3-Diferuloyl-sn-Glycerol and 1-Feruloyl-sn-Glycerol. Methods and Protocols. 2020; 3(1):8. https://doi.org/10.3390/mps3010008

Chicago/Turabian Style

Compton, David L.; Appell, Michael; Kenar, James A.; Evans, Kervin O. 2020. "Enzymatic Synthesis and Flash Chromatography Separation of 1,3-Diferuloyl-sn-Glycerol and 1-Feruloyl-sn-Glycerol" Methods Protoc. 3, no. 1: 8. https://doi.org/10.3390/mps3010008

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