Cocrystals and a Salt of the Bioactive Flavonoid: Naringenin
| Autor: | Nuala M. Maguire, Anita R. Maguire, Simon E. Lawrence, Balakrishna R. Bhogala, U. B. Rao Khandavilli, Abhijeet S. Sinha, Eliška Skořepová |
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| Rok vydání: | 2018 |
| Předmět: |
Naringenin
chemistry.chemical_classification 010405 organic chemistry Hydrogen bond Dimer Flavonoid food and beverages Salt (chemistry) General Chemistry 010402 general chemistry Condensed Matter Physics 01 natural sciences Cocrystal Medicinal chemistry 0104 chemical sciences 3. Good health chemistry.chemical_compound Solubility chemistry Intramolecular force General Materials Science Piperazinium salt |
| Zdroj: | Crystal Growth & Design. 18:4571-4577 |
| ISSN: | 1528-7505 1528-7483 |
| DOI: | 10.1021/acs.cgd.8b00557 |
| Popis: | 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) OH···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. |
| Databáze: | OpenAIRE |
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