ARS | Publication request: Purification of 2-monoacylglycerols using liquid CO2 extraction

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: February 2, 2012
Publication Date: July 27, 2012
Citation: Compton, D.L., Eller, F.J., Laszlo, J.A., Evans, K.O. 2012. Purification of 2-monoacylglycerols using liquid CO2 extraction. Journal of the American Oil Chemists' Society. 89(8):1529-1536.

Interpretive Summary: This research details the eco-friendly production and purification of chemical intermediates made from vegetable oils. Our mission is to develop new, value added uses for commodity crops and crop oils by developing bio-based chemicals and products that replace those made from petroleum. Much of today’s health and nutritional research investigates how the body uses and processes fats from food. This research has led to the development of naturally-derived synthetic fats, for example synthetic fats that mimic human milk fat. The manufacturing of these biomimetic fats depends on a particular unstable intermediate called a 2-monoacylglycerol (2-MAG). Our research shows how to make 2-MAG in excellent yield and high purity by a simple, environmentally benign method and purification. This new purification method will be of use to other scientists and researchers trying to design new, healthier, and more nutritious synthetic fats.

Technical Abstract: The fatty acid moiety of 2-monoacyl-sn-glycerol (2-MAG) undergoes spontaneous acyl migration to the sn-1(3) position, resulting in a thermodynamic equilibrium of approximately 1:9 of 2-MAG to 1-monoacyl-sn-glycerol (1-MAG). Spontaneous acyl migration is an impediment to synthesizing and isolating specific 2-MAG for use as intermediates in the synthesis of structured triacylglycerols (TAG). 2-Monooleoyl-sn-glycerol was synthesized by the enzymatic ethanolysis of triolein and isolated by liquid CO2 extraction. The resultant MAG, diacylglycerol (DAG), and fatty acid ethyl esters (FAEE) were quantified by **1H NMR and supercritical fluid chromatography (SFC). The low polarity of the CO2 and mild extraction temperature (25°C) resulted in very low spontaneous acyl migration rates, allowing the MAG to be isolated in 80% yield and in a very high 2-MAG:1-MAG ratios of = 93%.