Cocrystals and a salt of the bioactive flavonoid: naringenin

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Khandavilli, Udaya Bhaskara Rao
Skořepová, Eliška
Sinha, Abhijeet S.
Bhogala, Balakrishna R.
Maguire, Nuala M.
Maguire, Anita R.
Lawrence, Simon E.
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American Chemical Society
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Cocrystallization studies on Naringenin with 27 coformers have led to the formation of five new solid forms: a piperazinium salt (PIP+-NR-) and four cocrystals with the coformers flavone (FLV), 4-hydroxypyridine (4-HP), anthranilamide (ATA), and 4,4′-bipyridine (Bipy). Structural characterization reveals that the hydrogen bonded head to tail dimer motif in naringenin is maintained only in the cocrystal with flavone (NR-FLV). All four neutral cocrystals maintain the S(6) OH···O=C intramolecular hydrogen bond seen in naringenin with this carbonyl oxygen atom bifurcated. The piperazinium salt is the only structure in which the ether oxygen is involved in hydrogen bonding. Some of the structures display disorder in the chiral center of naringenin, making them anomalous racemic solid solutions. The solubility study revealed that the salt formation has significantly enhanced the solubility of naringenin, for example the piperazinium salt has enhanced solubility of >3,000 times that of the neutral parent compound.
Solubility , Naringenin , Piperazinium salt
Khandavilli, U. B. R., Skořepová, E., Sinha, A. S., Bhogala, B. R., Maguire, N. M., Maguire, A. R. and Lawrence, S. E. (2018) 'Cocrystals and a salt of the bioactive flavonoid: naringenin', Crystal Growth and Design. doi:10.1021/acs.cgd.8b00557
© 2018, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Crystal Growth and Design, © American Chemical Society, after peer review and technical editing by the publisher. To access the final edited and published work see