Physical characterization of oleanolic acid nonsolvate and solvates prepared by solvent recrystallization

Oleanolic acid is a naturally occurring compound used clinically in China for the treatment of hepatitis B. The solid-state chemistry of oleanolic acid recrystallized from a variety of solvents was investigated. Glassy materials were prepared from dichloromethane and chloroform solvents. The oleanolic acid non-solvate prepared from acetone (OA-acetone), and the two oleanolic acid solvates prepared from methanol (OA-methanol) and ethanol (OA-ethanol) were physicochemically characterized. Upon desolvation, both the methanol and ethanol solvates were found to undergo phase transformation to a crystalline phase similar to OA-acetone around 190-195 °C. The PXRD patterns of commercial pharmaceutical grade OA and the OA-methanol were similar, so the commercial form is probably desolvated oleanolic acid methanol solvate.