Synthesis and physical properties of EOE and EEO, triacylglycerols containing elaidic and oleic fatty acids

Symmetrical and non-symmetrical triacylglycerols (TAG) containing oleic (O; 9c-18:1) and elaidic (E; 9t-18:1) acids were required as part of a study relating the physical characteristics and functionality of trans-containing TAG with the mouth feel, taste characteristics and related characteristics desired by consumers in frying oils and pastries. To replace the trans isomers in frying oils-a significant part of frying oils prepared by partial hydrogenation of vegetable oils-without loss of the sensory properties desired by consumers, required the initiation of a study relating the structure of trans-containing TAG with such characteristics as melting range, drop points, and other crystalline properties. Elaidic acid was esterified to trielaidin (EEE), and the EEE partially converted (glycerol/p-toluenesulfonic acid) to a mixture containing ca. 40% DAG (the 1,3- and 1,2-isomers). The DAG fraction was separated by silica gel chromatography, the 1,3-dielaidylglycerol (1,3EE-DAG) isomer isolated (structural purity >99%) by crystallization from acetone and esterified with oleic acid (O) to yield EOE. The 1(3)O-MAG was purchased commercially and esterified with E acid to prepare OEE. Both syntheses yielded multi-gram quantities of EOE and EEO, in 80-85% yields, and with structural purities >99%. Thus, by careful selection of the thermodynamically more-stable MAG or DAG precursors, the symmetrical EOE and non-symmetrical EEO isomers could be readily synthesized, and their drop point and melting point values determined.