Graduation Year

2009

Document Type

Thesis

Degree

M.S.

Degree Granting Department

Chemistry

Major Professor

Michael J. Zaworotko, Ph.D.

Keywords

Supramolecular chemistry, Bioavailability, Hydrogen bond, Bcs classification, Solubility

Abstract

The cocrystallization of two or more pure compounds by crystal engineering to create a new functional material is of a great academic and industrial interest. Pharmaceutical cocrystallization has allured a lot of attention by means of altering the physicochemical properties of Active Pharmaceutical Ingredient (API) such as solubility, stability and bioavailability. Crystal engineering of nutraceuticals can produce novel compounds such as pharmaceutical cocrystals. To establish the importance of nutraceutical cocrystallization and its use; polyphenols, a major class of nutraceuticals and potential disease preventing agents, are the appropriate targets. The work herein focuses on two polyphenols, protocatechuic acid and quercetin, which are strong antioxidants. The cocrystals of quercetin have been synthesized, aiming to modify its poor water solubility and bioavailability which limits its usage. On the other hand, cocrystals of water soluble protocatechuic acid are also prepared to establish its use as a cocrystal former. Seven novel cocrystals of protocatechuic acid and two novel cocrystals of quercetin are obtained and are characterized by FTIR, DSC (Differential Scanning Calorimetry), PXRD (Powder X-Ray Diffraction), single crystal x-ray diffraction and TGA (Thermo Gravimetric Analysis). The new crystal forms have also been studied via dissolution. Dissolution studies show alteration in solubility of a target molecule by its cocrystal irrespective of solubility of the cocrystal former. Overall, the study helps in understanding the role of crystal engineering and its utility.

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