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Molecules 2011, 16(11), 9357-9367; doi:10.3390/molecules16119357

Stigmasterol-Based Novel Low Molecular Weight/Mass Organic Gelators

1 Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Faculty of Food and Biochemical Technology, Technická 5, 166 28 Prague 6, Czech Republic 2 Isotope Laboratory, Institute of Experimental Botany AS CR, v.v.i., Vídeňská 1083, 142 20 Prague 4, Czech Republic 3 Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
* Author to whom correspondence should be addressed.
Received: 25 October 2011 / Revised: 31 October 2011 / Accepted: 2 November 2011 / Published: 8 November 2011
(This article belongs to the Special Issue Steroids)
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Conjugates consisting of stigmasterol and L-phenylalanine, interconnected through short-chained dicarboxylic acyls by ester and amide bonds, respectively, were synthesized as potential low molecular weight/mass organic gelators (LMWGs/LMMGs). Their physico-chemical properties were subjected to investigation, especially their ability to form gels reversibly based on changes of the environmental conditions. Other self-assembly properties detectable by UV-VIS traces were measured in systems consisting of two miscible solvents (water/acetonitrile) with varying solvent ratios and using constant concentrations of the studied compounds. Partition and diffusion coefficients and solubility in water were calculated for the target conjugates. The conjugate 3a was the only compound from this series capable of forming a gel in 1-octanol. All three conjugates 3a–3c displayed supramolecular characteristics in the UV-VIS spectra.
Keywords: stigmasterol; L-phenylalanine; ester; amide; supramolecule; low molecular weight/mass organic gelators stigmasterol; L-phenylalanine; ester; amide; supramolecule; low molecular weight/mass organic gelators
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Šusteková, J.; Drašar, P.; Šaman, D.; Wimmer, Z. Stigmasterol-Based Novel Low Molecular Weight/Mass Organic Gelators. Molecules 2011, 16, 9357-9367.

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