Polymorphs of Curcumin and Its Cocrystals With Cinnamic Acid
| Autor: | Noopur Rathi, Vilas G. Gaikar, Anant Paradkar |
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| Rok vydání: | 2019 |
| Předmět: |
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Molecular Curcumin Pharmaceutical Science Infrared spectroscopy Antineoplastic Agents 02 engineering and technology Mole fraction 030226 pharmacology & pharmacy Cocrystal Cinnamic acid 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Differential scanning calorimetry X-Ray Diffraction Chemical Precipitation Hydrogen bond Enthalpy of fusion 021001 nanoscience & nanotechnology chemistry Cinnamates Solvents Thermodynamics Crystallization 0210 nano-technology Powder Diffraction Nuclear chemistry |
| Zdroj: | Journal of Pharmaceutical Sciences. 108:2505-2516 |
| ISSN: | 0022-3549 |
| DOI: | 10.1016/j.xphs.2019.03.014 |
| Popis: | We report formation of polymorphs and new eutectics and cocrystals of curcumin, a sparingly water-soluble active component in turmeric, structurally similar to cinnamic acid. The curcumin polymorphs were formed using liquid antisolvent precipitation, where acetone acted as a solvent and water was used as the antisolvent. The metastable form 2 of curcumin was successfully prepared in varied morphology over a wide range of solvent-to-antisolvent ratio and under acidic pH conditions. We also report formation of new eutectics and cocrystals of curcumin with cinnamic acid acting as a coformer. The binary phase diagrams were studied using differential scanning calorimetry and predicted formation of the eutectics at the curcumin mole fraction of 0.15 and 0.33, whereas a cocrystal was formed at 0.3 mole fraction of curcumin in the curcumin-cinnamic acid mixture. The formation of the cocrystal was supported with X-ray powder diffraction, the enthalpy of fusion values, Fourier-transform infrared spectroscopy, and scanning electron microscopy. The hydrogen bond interaction between curcumin and cinnamic acid was predicted from Fourier-transform infrared spectra, individually optimized curcumin and cinnamic acid structures by quantum mechanical calculations using Gaussian-09 and their respective unit cell packing structures. |
| Databáze: | OpenAIRE |
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