(E)-2-Benzylidenebenzocyclanones, part VIII: spectrophotometric determination of pKa values of some natural and synthetic chalcones and their cyclic analogues View Full Text


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Article Info

DATE

2011-09-24

AUTHORS

Ivan Kron, Zuzana Pudychová-Chovanová, Beáta Veliká, Juraj Guzy, Pál Perjési

ABSTRACT

UV–Vis spectrophotometry was used to determine acid dissociation constant (pKa) values of the natural flavonoids phloretin, phlorizin, naringenin, and naringin, as well as 4′-hydroxychalcone, 4′-(dimethylamino)chalcone, and their cyclic analogues. Comparison of the results with those previously reported for the natural flavonoids showed the applied method is a relatively straightforward and easy-to-perform technique for the determination of pKa values of compounds with relatively low solubility. Comparative analysis of the pKa values of the synthetic chalcones showed a strong correlation between the degree of conjugation and the acid strength of the respective compounds with different geometry. Our results provide further evidence that modification of the three-dimensional structure of open-chain bioactive compounds is the method of choice to modify not only their stereochemistry but also their physicochemical properties.Graphical abstract More... »

PAGES

13-17

References to SciGraph publications

  • 2006-04-01. Use of RP-TLC for Determination of log Pof Isomeric Chalcones and Cyclic Chalcone Analogues in JPC – JOURNAL OF PLANAR CHROMATOGRAPHY – MODERN TLC
  • 1983-03. Flavonoids and phylogenetic reconstruction in PLANT SYSTEMATICS AND EVOLUTION
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    http://scigraph.springernature.com/pub.10.1007/s00706-011-0633-0

    DOI

    http://dx.doi.org/10.1007/s00706-011-0633-0

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