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Issue 26, 2015
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Novel co-crystals of the nutraceutical sinapic acid

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Abstract

Sinapic acid (SA) is a nutraceutical with known anti-oxidant, anti-microbial, anti-inflammatory, anti-cancer, and anti-anxiety properties. Novel co-crystals of SA were prepared with co-formers belonging to the category of GRAS [isonicotinic acid (INC), nicotinamide (NIA)], non-GRAS [4-pyridinecarbonitrile (PYC)], and active pharmaceutical ingredients (APIs) [6-propyl-2-thiouracil (PTU)] list of compounds. Structural study based on the X-ray crystal structures revealed the intermolecular hydrogen-bonded interactions and molecular packing. The crystal structure of sinapic acid shows the anticipated acid–acid homodimer along with discrete hydrogen bonds between the acid carbonyl and the phenolic moiety. The robust acid–acid homodimer appears to be very stable and is retained in the structures of two co-crystals (SA·NIA and SA·PYC). In these cases, co-crystallization occurs via intermolecular phenol O–H⋯Naromatic hydrogen bonds between the co-formers. In the SA·PTU·2MeCN co-crystal the acid–acid homodimer gives way to the anticipated acid–amide heterodimer, with the phenolic moiety of SA hydrogen-bonded to acetonitrile. Attempts at obtaining the desolvated co-crystal led to lattice breakdown, thus highlighting the importance of acetonitrile in the formation of the co-crystal. Among the co-crystals examined, SA·INC (5 weeks), SA·NIA (8 weeks) and SA·PYC (5 weeks) were found to be stable under accelerated humidity conditions (40 °C, 75% RH), whereas SA·PTU·2MeCN decomposed after one week into individual components due to solvent loss.

Graphical abstract: Novel co-crystals of the nutraceutical sinapic acid

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Supplementary files

Article information


Submitted
21 Apr 2015
Accepted
29 May 2015
First published
29 May 2015

This article is Open Access

CrystEngComm, 2015,17, 4832-4841
Article type
Paper
Author version available

Novel co-crystals of the nutraceutical sinapic acid

A. S. Sinha, U. B. Rao Khandavilli, E. L. O’Connor, B. J. Deadman, A. R. Maguire and S. E. Lawrence, CrystEngComm, 2015, 17, 4832
DOI: 10.1039/C5CE00777A

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