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Conformational Trimorphism in an Ionic Cocrystal of Hesperetin

[Image: see text] We report the existence of conformational polymorphism in an ionic cocrystal (ICC) of the nutraceutical compound hesperetin (HES) in which its tetraethylammonium (TEA(+)) salt serves as a coformer. Three polymorphs, HESTEA-α, HESTEA-β and HESTEA-γ, were characterized by single-crys...

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Autores principales: Jin, Shasha, Haskins, Molly M., Andaloussi, Yassin H., Ouyang, Ruiling, Gong, Junbo, Zaworotko, Michael J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9634790/
https://www.ncbi.nlm.nih.gov/pubmed/36345389
http://dx.doi.org/10.1021/acs.cgd.2c00861
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author Jin, Shasha
Haskins, Molly M.
Andaloussi, Yassin H.
Ouyang, Ruiling
Gong, Junbo
Zaworotko, Michael J.
author_facet Jin, Shasha
Haskins, Molly M.
Andaloussi, Yassin H.
Ouyang, Ruiling
Gong, Junbo
Zaworotko, Michael J.
author_sort Jin, Shasha
collection PubMed
description [Image: see text] We report the existence of conformational polymorphism in an ionic cocrystal (ICC) of the nutraceutical compound hesperetin (HES) in which its tetraethylammonium (TEA(+)) salt serves as a coformer. Three polymorphs, HESTEA-α, HESTEA-β and HESTEA-γ, were characterized by single-crystal X-ray diffraction (SCXRD). Each polymorph was found to be sustained by phenol···phenolate supramolecular heterosynthons that self-assemble with phenol···phenol supramolecular homosynthons into C(3)(2)(7) H-bonded motifs. Conformational variability in HES moieties and different relative orientations of the H-bonded motifs resulted in distinct crystal packing patterns: HESTEA-α and HESTEA-β exhibit H-bonded sheets; HESTEA-γ is sustained by bilayers of H-bonded tapes. All three polymorphs were found to be stable upon exposure to humidity under accelerated stability conditions for 2 weeks. Under competitive slurry conditions, HESTEA-α was observed to transform to the β or γ forms. Solvent selection impacted the relationship between HESTEA-β (favored in EtOH) and HESTEA-γ (favored in MeOH). A mixture of the β and γ forms was found to be present following H(2)O slurry.
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spelling pubmed-96347902022-11-05 Conformational Trimorphism in an Ionic Cocrystal of Hesperetin Jin, Shasha Haskins, Molly M. Andaloussi, Yassin H. Ouyang, Ruiling Gong, Junbo Zaworotko, Michael J. Cryst Growth Des [Image: see text] We report the existence of conformational polymorphism in an ionic cocrystal (ICC) of the nutraceutical compound hesperetin (HES) in which its tetraethylammonium (TEA(+)) salt serves as a coformer. Three polymorphs, HESTEA-α, HESTEA-β and HESTEA-γ, were characterized by single-crystal X-ray diffraction (SCXRD). Each polymorph was found to be sustained by phenol···phenolate supramolecular heterosynthons that self-assemble with phenol···phenol supramolecular homosynthons into C(3)(2)(7) H-bonded motifs. Conformational variability in HES moieties and different relative orientations of the H-bonded motifs resulted in distinct crystal packing patterns: HESTEA-α and HESTEA-β exhibit H-bonded sheets; HESTEA-γ is sustained by bilayers of H-bonded tapes. All three polymorphs were found to be stable upon exposure to humidity under accelerated stability conditions for 2 weeks. Under competitive slurry conditions, HESTEA-α was observed to transform to the β or γ forms. Solvent selection impacted the relationship between HESTEA-β (favored in EtOH) and HESTEA-γ (favored in MeOH). A mixture of the β and γ forms was found to be present following H(2)O slurry. American Chemical Society 2022-10-04 2022-11-02 /pmc/articles/PMC9634790/ /pubmed/36345389 http://dx.doi.org/10.1021/acs.cgd.2c00861 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Jin, Shasha
Haskins, Molly M.
Andaloussi, Yassin H.
Ouyang, Ruiling
Gong, Junbo
Zaworotko, Michael J.
Conformational Trimorphism in an Ionic Cocrystal of Hesperetin
title Conformational Trimorphism in an Ionic Cocrystal of Hesperetin
title_full Conformational Trimorphism in an Ionic Cocrystal of Hesperetin
title_fullStr Conformational Trimorphism in an Ionic Cocrystal of Hesperetin
title_full_unstemmed Conformational Trimorphism in an Ionic Cocrystal of Hesperetin
title_short Conformational Trimorphism in an Ionic Cocrystal of Hesperetin
title_sort conformational trimorphism in an ionic cocrystal of hesperetin
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9634790/
https://www.ncbi.nlm.nih.gov/pubmed/36345389
http://dx.doi.org/10.1021/acs.cgd.2c00861
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