Abstract
Triacylglycerols (TAG) are the main component in fats and oils and a major component in many food and consumer products. These compounds are always asymmetric (about the sn-2position), while many diacid and all triacid TAG are chiral. To understand what effect this has on their crystallization behavior, model enantiopure (1,2-bisdecanoyl-3-palmitoyl-sn-glycerol) and racemic (bisdecanoyl-1(3)-palmitoyl-rac-glycerol) TAG were prepared and characterized. In addition, a binary phase diagram was prepared to investigate their phase behavior and the racemate’s crystalline tendency. For the subject compounds, infrared spectroscopy and X-ray powder diffraction data indicate the enantiopure TAG is β′-stable, whereas the racemic mixture is β-stable. In addition, based on the phase diagram, the high-melting form of the racemic mixture is a racemic compound (with a unit cell containing equal quantities of both enantiomers). Racemic (and near-racemic) mixtures also crystallize in a lower-melting metastable conglomerate β′ form. Thus, there are critical differences between the crystallization behavior of enantiopure and racemic TAG, and future investigations of these compounds should reflect these findings.
Published Version
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