Preparation of Diacid 1,3‐Diacylglycerols

Abstract A complete methodology (including synthesis, purification and analysis) for the preparation of 1,3‐DAG is described. For a successful synthesis project, the strengths and weaknesses of each particular process should be taken into account and measures taken to offset or balance potential weaknesses. To this end, we describe some of the challenges associated with: chemically and enzymatically catalyzed acylglycerol syntheses; recrystallization and flash chromatography for purification of partial acylglycerols; and thin‐layer chromatography (TLC) separation of DAG. For this work, 1‐MAG intermediates and subsequent diacid 1,3‐DAG were prepared using non‐enzymatic methods, whereas, monoacid 1,3‐DAG were prepared by enzymatic methods. It was not always possible to obtain pure samples of target compounds—in recrystallizations this is due to solid solution formation and co‐crystallization and in chromatographic separations it is due to co‐elution of components with similar R f . Furthermore, TLC R f of DAG is determined by two main factors: acyl chain length and positional isomerism. Interestingly, while the role of positional isomerism is well‐known, the role of acyl chain length in these separations has only recently come to light.