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Influence of Solid Supports on Acyl Migration in 2-Monoacylglycerols: Purification of 2-MAG via Flash Chromatography

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Journal of the American Oil Chemists' Society

Abstract

Soybean oil 2-monoacylglycerol (2-MAG) was synthesized via the Novozym 435-catalyzed ethanolysis of triacylglycerols and purified by conventional liquid–liquid extraction. The 2-MAG was subjected to incubation at 20 and 40 °C in the presence of five solid commercial support materials, Lewatit, Silica Gel 60, Alumina–Neutral Brockman Activity 1, Amberlyst-15, and SBA-15, to determine their effects on acyl migration rates. Lewatit and SBA-15 did not catalyze acyl migration rates after 144 h, while silica gel slightly increased migration rates. The more polar alumina and the cationic Amberlyst 15 significantly increased migration rates. Flash chromatography purification of 2-MAG using silica gel as the immobile phase developed with an acetone/hexane binary gradient proved to be a comparable purification method to liquid–liquid extraction, resulting in 60 % 2-MAG yield, no residual triacylglycerol, diacylglycerol, or glycerol co-products, and a 95 mol% 2-MAG purity vs. 1-MAG, demonstrating that flash chromatography did not catalyze acyl migration.

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Authors and Affiliations

  1. Renewable Product Technology Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, Peoria, IL, 61604, USA

    David L. Compton, Joseph A. Laszlo & Kervin O. Evans

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  1. David L. Compton
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  2. Joseph A. Laszlo
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  3. Kervin O. Evans
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Correspondence to David L. Compton.

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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.

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Compton, D.L., Laszlo, J.A. & Evans, K.O. Influence of Solid Supports on Acyl Migration in 2-Monoacylglycerols: Purification of 2-MAG via Flash Chromatography. J Am Oil Chem Soc 90, 1397–1403 (2013). https://doi.org/10.1007/s11746-013-2274-4

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  • DOI: https://doi.org/10.1007/s11746-013-2274-4

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