Separation of the enantiomers of 1-alkyl-2-acyl-rac-glycerol and of 1-alkyl-3-acyl-rac-glycerol by high performance liquid chromatography on a chiral column

High performance liquid chromatographic separations of two enantiomeric pairs of 1-alkyl-2-acyl-rac-glycerol (1-alkyl-2-acyl- and 3-alkyl-2-acyl-sn-glycerols) and 1-alkyl-3-acyl-rac-glycerol (1-alkyl-3-acyl- and 3-alkyl-1-acyl-sn-glycerols) as 3,5-dinitrophenylurethanes (3,5-DNPUs) were carried out on a chiral stationary phase, N-(R)-1-(α-naphthyl)ethylaminocarbonyl-(S)-valine chemically bonded to γ-aminopropyl silanized silica (Sumipax OA-4100). Good separation of the enantiomers of 1-hexadecyl-2-hexadecanoyl-rac-glycerol was easily achieved within 10 min using hexane/ethylene dichloride/ethanol (80∶20∶1, v/v/v) as a mobile phase. Separation of the enantiomers of 1-hexadecyl-3-hexadecanoyl-rac-glycerol was more difficult and required about 80 min to achieve satisfactory peak resolution (0.8) using hexane/ethylene dichloride/ethanol (250∶20∶1, v/v/v) as a mobile phase. Presented at the American Oil Chemists' Society 79th Annual Meeting, Phoenix, AZ, May, 1988.