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Issue 1, 2009
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Ionic liquids with dual biological function: sweet and anti-microbial, hydrophobic quaternary ammonium-based salts

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Abstract

The dual nature of ionic liquids has been exploited to synthesize materials that contain two independent biological functions by combining anti-bacterial quaternary ammonium compounds with artificial sweetener anions. The synthesis and physical properties of eight new ionic liquids, didecyldimethylammonium saccharinate ([DDA][Sac]), didecyldimethylammonium acesulfamate ([DDA][Ace]), benzalkonium saccharinate ([BA][Sac]), benzalkonium acesulfamate ([BA][Ace]), hexadecylpyridinium saccharinate ([HEX][Sac]), hexadecylpyridinium acesulfamate ([HEX][Ace]), 3-hydroxy-1-octyloxymethylpyridinium saccharinate ([1-(OctOMe)-3-OH-Py][Sac]), and 3-hydroxy-1-octyloxymethylpyridinium acesulfamate ([1-(OctOMe)-3-OH-Py][Ace]), are reported, as well as the single crystal structures for [HEX][Ace] and [1-(OctOMe)-3-OH-Py][Sac]. Determination of anti-microbial activities is described for six of the ILs. While some exhibited decreased anti-microbial activity others showed a dramatic increase. For two of the ionic liquids, [DDA][Sac] and [DDA][ACE], oral toxicity, skin irritation, and deterrent activity was also established. Unfortunately, both ILs received a Category 4 (harmful) rating for oral toxicity and skin irritation. However, deterrent activity experiments point to use as an insect deterrent, as both ILs scored either “very good” or “good” against several types of insects.

Graphical abstract: Ionic liquids with dual biological function: sweet and anti-microbial, hydrophobic quaternary ammonium-based salts

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Publication details

The article was received on 30 Jul 2008, accepted on 29 Aug 2008 and first published on 22 Oct 2008


Article type: Paper
DOI: 10.1039/B813213P
New J. Chem., 2009,33, 26-33

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    Ionic liquids with dual biological function: sweet and anti-microbial, hydrophobic quaternary ammonium-based salts

    W. L. Hough-Troutman, M. Smiglak, S. Griffin, W. Matthew Reichert, I. Mirska, J. Jodynis-Liebert, T. Adamska, J. Nawrot, M. Stasiewicz, R. D. Rogers and J. Pernak, New J. Chem., 2009, 33, 26
    DOI: 10.1039/B813213P

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