New pharmaceutical salts containing pyridoxine

Cvetkovski, Aleksandar and Ferretti, Valeria and Bertolasi, Valerio (2017) New pharmaceutical salts containing pyridoxine. Acta Crystallographica Section C: Structural Chemistry, Acta Cryst. C, C (73). pp. 1064-1070. ISSN 2053-2296

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Two mixed crystals were obtained by crystallizing the active pharmaceutical ingre­dient pyridoxine [systematic name: 4,5-bis­(hy­droxy­meth­yl)-2-methyl­pyri­din-3-ol, PN] with (E)-3-(4-hy­droxy-3-meth­oxy­phen­yl)prop-2-enoic acid (feru­lic acid) and 4-hy­droxy-3,5-di­meth­oxy­benzoic acid (syringic acid). PN and the coformers crystallize in the form of pharmaceutical salts in a 1:1 stoichiometric ratio, namely 3-hy­droxy-4,5-bis­(hy­droxy­meth­yl)-2-methyl­pyridin-1-ium (E)-3-(4-hy­droxy-3-meth­oxy­phen­yl)prop-2-enoate, C8H12NO3+·C9H9O5−, and 3-hy­droxy-4,5-bis­(hy­droxy­meth­yl)-2-methyl­pyridin-1-ium 4-hy­droxy-3,5-di­meth­oxy­benzoate monohydrate, C8H12NO3+·C10H11O5−·H2O, the proton exchange between PN and the acidic partner being supported by the differences of the pKa values of the two components and by the C—O bond lengths of the carb­oxy­late groups. Besides complex hydrogen-bonding networks, π–π inter­actions between aromatic moieties have been found to be important for the packing architecture in both crystals. Hirshfeld surface analysis was used to explore the inter­molecular inter­actions in detail and compare them with the inter­actions found in similar pyridoxine/carb­oxy­lic acid salts.

Item Type: Article
Subjects: Medical and Health Sciences > Basic medicine
Natural sciences > Chemical sciences
Divisions: Faculty of Medical Science
Depositing User: Aleksandar Cvetkovski
Date Deposited: 24 Jan 2018 14:34
Last Modified: 24 Jan 2018 14:34

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