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

Henry H.Y. Tong, H. B. Wu, Y. Zheng, J. Xi, Albert H.L. Chow, Chak K. Chan

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)195-202
Number of pages8
JournalInternational Journal of Pharmaceutics
Volume355
Issue number1-2
DOIs
Publication statusPublished - 1 May 2008

Keywords

  • Oleanolic acid
  • Solid-state transition
  • Solvates
  • Solvent recrystallization

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