Premium
Synthesis and Physical Properties of EOE and EEO, Triacylglycerols Containing Elaidic and Oleic Fatty Acids
Author(s) -
Adlof R. O.,
List G. R.
Publication year - 2007
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-007-1056-2
Subject(s) - elaidic acid , chemistry , melting point , oleic acid , acetone , organic chemistry , fatty acid , yield (engineering) , crystallization , chromatography , biochemistry , linoleic acid , materials science , metallurgy
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.