Novel co-crystals of the nutraceutical sinapic acid

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dc.contributor.authorSinha, Abhijeet S.
dc.contributor.authorKhandavilli, Udaya Bhaskara Rao
dc.contributor.authorO'Connor, Emma L.
dc.contributor.authorDeadman, Benjamin J.
dc.contributor.authorMaguire, Anita R.
dc.contributor.authorLawrence, Simon E.
dc.contributor.funderScience Foundation Irelanden
dc.date.accessioned2016-01-12T16:41:21Z
dc.date.available2016-01-12T16:41:21Z
dc.date.issued2015-05-29
dc.description.abstractSinapic 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.sponsorshipScience Foundation Ireland (SFI Grant 12/RC/2275, SFI Grant 05/PICA/B802/EC07); University College Cork (UCC 2013 Strategic Research Fund)en
dc.description.statusPeer revieweden
dc.description.versionPublished Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationSINHA, 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/C5CE00777Aen
dc.identifier.doi10.1039/C5CE00777A
dc.identifier.endpage4841en
dc.identifier.issn1466-8033
dc.identifier.issued26en
dc.identifier.journaltitleCrystEngCommen
dc.identifier.startpage4832en
dc.identifier.urihttps://hdl.handle.net/10468/2180
dc.identifier.volume17en
dc.language.isoenen
dc.publisherThe Royal Society of Chemistryen
dc.rights© 2015, the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.en
dc.rights.urihttp://creativecommons.org/licenses/by/3.0/en
dc.subjectHydrogen bondsen
dc.subject3,5-Dimethoxy-4-hydroxycinnamic aciden
dc.subjectCocrystalsen
dc.subjectDerivativesen
dc.subjectSolubilityen
dc.subjectPropylthiouracilen
dc.subjectArchitecturesen
dc.subjectStabilityen
dc.subjectPhenolsen
dc.titleNovel co-crystals of the nutraceutical sinapic aciden
dc.typeArticle (peer-reviewed)en
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