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Naringenin complexes with copper ions: potentiometric studies

Brodowska K.

Biotechnology and Food Science

2013

Vol. 77, nr 1

45--53

Flavanones belong to the group of active flavonoid compounds, rarely occurring in the plant kingdom and are found in many foodstuffs (naringenin and derivatives) and medicinal plant materials. Many studies have demonstrated a relationship between dietary intake of phenolic compounds and reduced risk of cancer and cardiovascular disease. Accordingly, during over several years, flavonoids have gained increasing interest and numerous studies have shown that they possess beneficial properties having a great influence on human health. Acid dissociation constants are believed to be the most useful physico-chemical parameters which describe the extent of ionization of functional groups as a function of pH. It is very important in research areas such as pharmaceutical drug discovery and development due to vital role in understanding the pharmacodynamic properties of new drug substances. Flavonoids are characterized by insolubility in water while they are soluble in organic solvents. Exploiting mixed solvents, especially organic solvent – water mixtures, enables a good alternative for researching on compounds which are inconspicuously soluble or insoluble in water. In this study the dissociation constant of naringenin and its complex with Cu(II) have been determined in aqueous – DMSO solvent mixtures to examine the dependence of their acid-base equilibria on number of substrates.

Potentiometric determination of pKa values of 1,4,5,8-tetrahydroxy-9-oxo-10-pentyl- 9,10-dihydro-acridine-2,3,6,7-tetracarboxylic acid (TPAT) extracted from Laurus Nobilis

Ibaoglu K., Sari H., Tuzen M., Mendil D., Soylak M.

Chemia Analityczna

2004

Vol. 49, No. 5

635-642

The pKa values of 1,4,5,8-tetrahydroxy-9-oxo-10-pentyl-9,10-dihydro-acridine-2,3,6,7-tetracarboxylic acid (TPAT) extracted from Laurus nobilis were determined by Molspin potentiometric titration at 25°C in the presence of 0.1 mol dm-3 NaCl. The pKa values were calculated using SUPERQUAD computer program. Initially deprotonation occurs in carboxylic groups, then at the nitrogen atom of the alkyl group, and finally at the hydroxylic groups of TPAT. The following pKa values were computed: 2.65, 3.36, 4.08, 5.43, 6.84, 9.30, 10.42 and 10.53.

Wyznaczono wartości pKa kwasu 1,4,5,8-tetrahydroksy-9-okso-1O-pentylo-9,10-dihydro-akrydyno-2,3,6,7-tetrakarboksylowego (TPAT) wyekstrahowanego z Laurus nobilis. Wyznaczanie pK przeprowadzono metodą potencjometry c zn ego miareczkowania Molspin'a wtemp. 25°C w obecności 0,1 mol dm(-3) NaCl. Wartości pK. obliczono przy użyciu programu komputerowego SUPERQUAD. W pierwszym rzędzie dysocjacji kwasowej ulegają grupy karboksylowe, później grupa =NH+ i na końcu grupy hydroksylowe. Dla poszczególnych stopni dysocjacji kwasowej wyliczono następujące wartości pK (a): 2,65; 3,36; 4,08; 5,43; 6,84:9,30; 10,42 and 10,53.