The Bioenhancer Piperine is at Least Trimorphic

Polymer-induced heteronucleation
(PIHn), a powerful crystalline
polymorph discovery method, has revealed two novel polymorphs of the
low solubility bioenhancer piperine. Both of these forms exhibit enhanced
solubility when compared to the commercial polymorph, thereby potentially
improving the efficacy of piperine as a bioenhancer. Structural comparison
of the three forms reveals that π–π interactions
are only present in the two newly discovered forms. Combined with
the stability data, this reveals that despite the extended conjugation
present in the molecule such interactions are not preferred in the
solid state.