Crystallization Behavior and Crystallographic Properties of dl-Arabinose and dl-Xylose Diastereomer Sugars.

Abstract

Natural sugar molecules such as xylose and arabinose exhibit sweetness profiles similar to sucrose, which makes them a valuable alternative in low-calorie foods as well as excipients or cocrystallization agents in pharmaceutical formulations. Xylose and arabinose are also chiral diastereomers that can exhibit specific crystallization behavior. In this work, the solid-state landscapes of the chiral pairs of both xylose and arabinose have been investigated to determine whether racemic compounds or conglomerates are formed. Furthermore, single crystals of xylose and arabinose have been grown and characterized by X-ray diffraction and optical microscopy to study their crystallographic properties and relate them to the crystallization behavior. Differential scanning calorimetry (DSC) measurements were used to determine the phase diagrams of the two analyzed chiral systems. The solubilities of the different solid forms of xylose and arabinose were measured in different solvent mixtures by a thermogravimetric method. An analysis was conducted to assess the main thermodynamic parameters and the activity coefficients of the compounds in solution. Finally, slurry experiments in a 50:50 w/w ethanol/water solvent have also been performed to determine the relative stability of each solid form and the kinetics of transformation in this solvent mixture. It was found that dl-arabinose crystallizes as a stable racemic compound, which transforms quickly from its constituent enantiomers when in solution; whereas d- and l-xylose molecules crystallize separately as a conglomerate.