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.