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acylglycerols (i.e., 1,2- from 1,3-DAG and 2- from
1-MAG) with minimal acyl migration [16]. Evidently, for
DAG, Rf is determined by both positional isomerism and
the length of the shortest acyl chain (Table 2). This is of
little consequence in the analysis of DAG from a typical fat
or oil since they have such a narrow range of FA. In
contrast, the separation of milk fat DAG by boric acid TLC
is exceedingly complex since milk fat has long-, medium-
and short-chains. Thus, milk fat DAG separate into
numerous fractions on the basis of chain-length and posi-
tional isomerism [35].
In retrospect, it is evident that the proportion of reactants
and reaction times can be adjusted to achieve better results
based on the separation technology employed (Table 5).
For example, 1,3-DAG are less soluble in solvent than
either TAG or 1,2-DAG but more soluble than MAG,
therefore, purification by recrystallization will benefit if
TAG rather than MAG is the predominant byproduct.
Likewise, for purification by flash chromatography, 1,2- and
1,3-DAG have similar Rf and consequently, can be difficult
to separate. Therefore, minimizing 1,2-DAG formation (by
reducing reaction times) can be beneficial to chromato-
graphic separation. In addition, MAG tend to be retained
near the origin, whereas, TAG elute before DAG, thus,
MAG would be favored over TAG as byproducts in this
situation. All told, this work contains information critical to
lab-scale production of synthetic acylglycerols and pro-
vides an excellent starting point for optimal production of
1,3-DAG.
Acknowledgments Financial support for this project was provided
by Dairy Farmers of Ontario, Ontario Centres of Excellence and
National Sciences and Engineering Research Council of Canada; we
are grateful for their generosity. Thanks also to Japan VAM &
POVAL Co., Ltd. for their donation of vinyl esters of fatty acids.
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