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    Polymorphs of Curcumin and Its Cocrystals With Cinnamic Acid

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    Publication date
    2019-08
    Author
    Rathi, N.
    Paradkar, Anant R.
    Gaikar, V.G.
    Keyword
    Curcumin
    Cinnamic acid
    Eutectic
    Cocrystal
    Polymorphs
    Antisolvent precipitation
    Rights
    (c) 2019 Elsevier. Reproduced in accordance with the publisher's self-archiving policy. This manuscript version is made available under the CC-BY-NC-ND 4.0 license (http://creativecommons.org/licenses/by-nc-nd/4.0/)
    Peer-Reviewed
    Yes
    
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    Abstract
    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.
    URI
    http://hdl.handle.net/10454/17014
    Version
    Accepted manuscript
    Citation
    Rathi N, Paradkar AR and Gaikar VG (2019) Polymorphs of Curcumin and Its Cocrystals With Cinnamic Acid. Journal of Pharmaceutical Sciences. 108(8): 2505-2516.
    Link to publisher’s version
    https://doi.org/10.1016/j.xphs.2019.03.014
    Type
    Article
    Collections
    Life Sciences Publications

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