Novel co-crystals of the nutraceutical sinapic acid

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dc.contributor.author Sinha, Abhijeet S.
dc.contributor.author Khandavilli, Udaya Bhaskara Rao
dc.contributor.author O'Connor, Emma L.
dc.contributor.author Deadman, Benjamin J.
dc.contributor.author Maguire, Anita R.
dc.contributor.author Lawrence, Simon E.
dc.date.accessioned 2016-01-12T16:41:21Z
dc.date.available 2016-01-12T16:41:21Z
dc.date.issued 2015-05-29
dc.identifier.citation SINHA, A. S., KHANDAVILLI, U. B. R., O'CONNOR, E. L., DEADMAN, B. J., MAGUIRE, A. R. & LAWRENCE, S. E. 2015. Novel co-crystals of the nutraceutical sinapic acid. CrystEngComm, 17, 4832-4841. http://dx.doi.org/10.1039/C5CE00777A en
dc.identifier.volume 17 en
dc.identifier.issued 26 en
dc.identifier.startpage 4832 en
dc.identifier.endpage 4841 en
dc.identifier.issn 1466-8033
dc.identifier.uri http://hdl.handle.net/10468/2180
dc.identifier.doi 10.1039/C5CE00777A
dc.description.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[middle dot]NIA and SA[middle dot]PYC). In these cases, co-crystallization occurs via intermolecular phenol O-H[three dots, centered]Naromatic hydrogen bonds between the co-formers. In the SA[middle dot]PTU[middle dot]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[middle dot]INC (5 weeks), SA[middle dot]NIA (8 weeks) and SA[middle dot]PYC (5 weeks) were found to be stable under accelerated humidity conditions (40 [degree]C, 75% RH), whereas SA[middle dot]PTU[middle dot]2MeCN decomposed after one week into individual components due to solvent loss. en
dc.description.sponsorship Science Foundation Ireland (SFI Grant 12/RC/2275, SFI Grant 05/PICA/B802/EC07); University College Cork (UCC 2013 Strategic Research Fund) en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher The Royal Society of Chemistry en
dc.rights © 2015, the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. en
dc.rights.uri http://creativecommons.org/licenses/by/3.0/ en
dc.subject Hydrogen bonds en
dc.subject 3,5-Dimethoxy-4-hydroxycinnamic acid en
dc.subject Cocrystals en
dc.subject Derivatives en
dc.subject Solubility en
dc.subject Propylthiouracil en
dc.subject Architectures en
dc.subject Stability en
dc.subject Phenols en
dc.title Novel co-crystals of the nutraceutical sinapic acid en
dc.type Article (peer-reviewed) en
dc.internal.authorcontactother Simon Lawrence, Chemistry, University College Cork, Cork, Ireland. +353-21-490-3000 Email: simon.lawrence@ucc.ie en
dc.internal.availability Full text available en
dc.description.version Published Version en
dc.internal.rssid 303734685
dc.contributor.funder Science Foundation Ireland en
dc.description.status Peer reviewed en
dc.identifier.journaltitle CrystEngComm en
dc.internal.IRISemailaddress simon.lawrence@ucc.ie
dc.internal.IRISemailaddress simon.lawrence@ucc.ie en


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© 2015, the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Except where otherwise noted, this item's license is described as © 2015, the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
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