Mechanosynthesis of Piperine Cocrystals with an Aromatic Benzoic Acid Analogue and Their Physicochemical Property Study

Cocrystallization of piperine (PIPE), a natural alkaloid with several GRAS coformers, namely, 4HBA, 26DHBA, and PABA, resulted in the formation of new cocrystals. All of the synthesized cocrystals were further characterized using PXRD and single-crystal XRD analysis. Based on our investigation, it was observed that PIPE•PABA monohydrate cocrystal is the most stable form among all the synthesized cocrystals and does not undergo cocrystal dissociation and/or phase transformation under a humid environment. On the other hand, slurry stirring shows possible phase transformation of the PIPE•4HBA cocrystal and dissociation in the case of the PIPE•26DHBA cocrystal. The absence of a hydrogen bond donor group in PIPE might be the reason behind limited reports on PIPE cocrystals.