ABSTRACT

The solubility of quercetin, isoquercitrin, rutin, chrysin, naringenin, and hesperetin was quantified in acetonitrile, acetone, and tert-amyl alcohol. The solubility was strongly affected by both the nature of the solvent and the flavonoid structure. The highest solubility was obtained in acetonitrile for hesperetin (85 mmolaL-1) and naringenin (77 mmolaL-1) and in acetone (80 mmolaL-1) for quercetin. The lowest solubility value was obtained with rutin in acetonirile (0.50 mmolaL-1). The thermodynamic properties of flavonoids were also measured (melting point, enthalpy of fusion, and solid heat capacity) and predicted (liquid heat capacity, solid phase activity, and activity coefficient). Glycosylated flavonoids are characterized by a low melting point and a high enthalpy of fusion compared to the aglycon ones. Contrary to the data reported for other compounds, there is no clear correlation between the solubility of flavonoids and their thermodynamic properties. However, the conformational study showed that the flavonoids having a torsion angle OC2C1centsC6cents of 40deg are characterized by a high solubility.

Compounds

#	Formula	Name
1	C27H30O16	rutin
2	C15H12O5	4',5,7-trihydroxyflavanone
3	C16H14O6	2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
4	C15H10O4	5,7-dihydroxyflavone
5	C15H10O7	quercetin
6	C21H20O12	isoquercitrin
7	C4H6O2	vinyl acetate
8	C2H3N	acetonitrile
9	C5H12O	2-methylbutan-2-ol
10	C3H6O	acetone

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	1	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	1	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	1	Molar heat capacity at constant pressure, J/K/mol ; Crystal	Temperature, K; Crystal Pressure, kPa; Crystal		Crystal	Small sample (50 mg) DSC	1
POMD	2	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	2	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	2	Molar heat capacity at constant pressure, J/K/mol ; Crystal	Temperature, K; Crystal Pressure, kPa; Crystal		Crystal	Small sample (50 mg) DSC	1
POMD	3	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	3	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	3	Molar heat capacity at constant pressure, J/K/mol ; Crystal	Temperature, K; Crystal Pressure, kPa; Crystal		Crystal	Small sample (50 mg) DSC	1
POMD	4	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	4	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	4	Molar heat capacity at constant pressure, J/K/mol ; Crystal	Temperature, K; Crystal Pressure, kPa; Crystal		Crystal	Small sample (50 mg) DSC	1
POMD	5	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	5	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	5	Molar heat capacity at constant pressure, J/K/mol ; Crystal	Temperature, K; Crystal Pressure, kPa; Crystal		Crystal	Small sample (50 mg) DSC	1
POMD	6	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	6	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	6	Molar heat capacity at constant pressure, J/K/mol ; Crystal	Temperature, K; Crystal Pressure, kPa; Crystal		Crystal	Small sample (50 mg) DSC	1
POMD	8 1	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid		Liquid Crystal - 1	SPECTR	1
POMD	8 6	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid Crystal - 6	SPECTR	3
POMD	8 5	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid		Liquid Crystal - 5	SPECTR	1
POMD	8 5	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid Crystal - 5	SPECTR	4
POMD	8 4	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid		Liquid Crystal - 4	SPECTR	1
POMD	8 2	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid		Liquid Crystal - 2	SPECTR	1
POMD	8 2	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid Crystal - 2	SPECTR	3
POMD	8 3	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid		Liquid Crystal - 3	SPECTR	1
POMD	8 3	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid Crystal - 3	SPECTR	3
POMD	9 5	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid		Liquid Crystal - 5	SPECTR	1
POMD	10 5	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid		Liquid Crystal - 5	SPECTR	1
POMD	9 6	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid		Liquid Crystal - 6	SPECTR	1
POMD	10 6	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid		Liquid Crystal - 6	SPECTR	1
POMD	9 1	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid		Liquid Crystal - 1	SPECTR	1
POMD	10 1	Amount concentration (molarity), mol/dm3 ; Liquid	Temperature, K; Liquid Pressure, kPa; Liquid		Liquid Crystal - 1	SPECTR	1
POMD	8 7 5	Amount concentration (molarity), mol/dm3 - 5 ; Liquid	Temperature, K; Liquid Amount concentration (molarity), mol/dm3 - 7; Liquid Pressure, kPa; Liquid		Liquid Crystal - 5	SPECTR	1
POMD	8 7 6	Amount concentration (molarity), mol/dm3 - 6 ; Liquid	Temperature, K; Liquid Amount concentration (molarity), mol/dm3 - 7; Liquid Pressure, kPa; Liquid		Liquid Crystal - 6	SPECTR	1

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

Solubility of Flavonoids in Organic Solvents

Chebil, L.[Latifa], Humeau, C.[Catherine], Anthoni, J.[Julie], Dehez, F.[Francois], Engasser, J.-M.[Jean-Marc], Ghoul, M.[Mohamed]

ABSTRACT