Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

Solubilities of Naringin and Naringenin in Different Solvents and Dissociation Constants of Naringenin

Zhang, L.[Liqin], Song, L.[Li], Zhang, P.[Peipei], Liu, T.[Tingting], Zhou, L.[Li], Yang, G.[Guangde], Lin, R.[Rong], Zhang, J.[Jiye]
J. Chem. Eng. Data 2015, 60, 3, 932-940
ABSTRACT
The solubilities of naringin and naringenin in methanol, isopropanol, ethyl acetate, petroleum ether, n-butanol, and hexane were measured by using UV spectrophotometric methods at the maximum absorption wavelength of (283 and 372) nm from (288.15 to 328.15) K. The solubilities of naringin and naringenin in different solvents increase with an increase of temperature. The solubility of naringin in the six solvents was in the order methanol greater than ethyl acetate greater than n-butanol greater than isopropanol greater than petroleum ether greater than hexane, and the solubility of naringenin in these solvents follows the order ethyl acetate greater than isopropanol greater than methanol greater than n-butanol greater than petroleum ether greater than hexane. The solubility of naringenin was significantly higher than naringin in all selected solvents because of the more similar polarity of naringenin with solvents. The solubilities of naringin and naringenin are calculated by using the modified Apelblat equation model, ideal model, and the ?H equation model. From solubility data, the changes of dissolution enthalpy, entropy, and the free Gibbs energy of naringin and naringenin in six solvents were also calculated using the van t Hoff equation. The course of naringin and naringenin dissolving in the selected solvents in the experimental temperature range was endothermic. The dissociation constants (pKa) of naringenin were determined at 298.2 K by ultraviolet (UV) spectroscopy method. The pKa1 and pKa2 values of naringenin are 7.05 +- 0.06 and 8.84 +- 0.08.
Compounds
# Formula Name
1 C15H12O5 4',5,7-trihydroxyflavanone
2 C27H32O14 naringin
3 CH4O methanol
4 C3H8O propan-2-ol
5 C4H8O2 ethyl acetate
6 C4H10O butan-1-ol
7 C6H14 hexane
Datasets
The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type Compound-# Property Variable Constraint Phase Method #Points
  • POMD
  • 3
  • 2
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • UV-vis spectrophotometry
  • 9
  • POMD
  • 4
  • 2
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • UV-vis spectrophotometry
  • 9
  • POMD
  • 5
  • 2
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • UV-vis spectrophotometry
  • 9
  • POMD
  • 6
  • 2
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • UV-vis spectrophotometry
  • 9
  • POMD
  • 7
  • 2
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • UV-vis spectrophotometry
  • 9
  • POMD
  • 3
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • UV-vis spectrophotometry
  • 9
  • POMD
  • 4
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • UV-vis spectrophotometry
  • 9
  • POMD
  • 5
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • UV-vis spectrophotometry
  • 9
  • POMD
  • 6
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • UV-vis spectrophotometry
  • 9
  • POMD
  • 7
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • UV-vis spectrophotometry
  • 9