2
0
2016
tan
zho
0
journal
Original
Tang, N.[Ning]
Zhong, J.[Jialun]
Yan, W.[Weidong]
J. Chem. Eng. Data
2016
2020-09-29
Solubilities of Three Flavonoids in Different Natural Deep Eutectic Solvents at T = (288.15 to 328.15) K
The solubilities of phloretin, phlorizin, and naringin dihydrochacone (naringin DC) respectively were determined in a ternary system made of natural deep eutectic solvents (NADES) at the temperature range from 288.15 to 328.15 K with an analytical method. Compared with the solubility of phloretin in water, there was a dramatic improvement in the solubility of phloretin in the selected NADES, especially in CCiH and CSH. The density and viscosity of four kinds of NADES choline chloride + glucose + H2O, choline chloride + citric acid + H2O, citric acid + glucose + H2O, and choline chloride + sucrose + H2O were studied in this work. The solubility data were correlated with Apelblat equation and h equation. The fitted results showed that the models are capable of representing the data with high accuracy.
10.1021/acs.jced.6b00552
12
61
4203-4208
1
InChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2
VGEREEWJJVICBM-UHFFFAOYSA-N
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
phloretin
C15H14O5
1
Commercial source
1
95
2
Stated by supplier
2
Crystallization from solution
3
99
2
HPLC
2
InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21?/m1/s1
IOUVKUPGCMBWBT-MKJMBMEGSA-N
phlorizin
1-(2,4-dihydroxy-6-(((3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-3-(4-hydroxyphenyl)propan-1-one
C21H24O10
1
Commercial source
1
95
2
Stated by supplier
2
Crystallization from solution
3
99
2
HPLC
3
InChI=1S/C27H34O14/c1-11-20(33)22(35)24(37)26(38-11)41-25-23(36)21(34)18(10-28)40-27(25)39-14-8-16(31)19(17(32)9-14)15(30)7-4-12-2-5-13(29)6-3-12/h2-3,5-6,8-9,11,18,20-29,31-37H,4,7,10H2,1H3/t11-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
CWBZAESOUBENAP-QVNVHUMTSA-N
naringin dihydrochalcone
C27H34O14
1
Commercial source
1
90
1
Stated by supplier
2
Crystallization from solution
3
99
2
HPLC
4
InChI=1S/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1
SGMZJAMFUVOLNK-UHFFFAOYSA-M
choline chloride
(.beta.-hydroxyethyl)trimethylammonium chloride
(2-hydroxyethyl)trimethylammonium chloride
2-hydroxy-N,N,N-trimethylethanaminium chloride
cholinium chloride
trimethyl(2-hydroxyethyl)ammonium chloride
C5H14ClNO
1
Commercial source
1
99
2
Stated by supplier
5
InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
KRKNYBCHXYNGOX-UHFFFAOYSA-N
citric acid
1,2,3-propanetricarboxylic acid, 2-hydroxy-
2-hydroxy-1,2,3-propanetricarboxylic acid
C6H8O7
1
Commercial source
1
99.5
3
Stated by supplier
6
InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6+/m0/s1
GZCGUPFRVQAUEE-SLPGGIOYSA-N
D-glucose
(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal
D(+)-glucose
dextrose
C6H12O6
1
Commercial source
1
99.5
3
Stated by supplier
7
InChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1
CZMRCDWAGMRECN-UGDNZRGBSA-N
D-sucrose
(2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
.beta.-D-fructofuranosyl .alpha.-D-glucopyranoside
D-(+)-saccharose
D-(+)-sucrose
C12H22O11
1
Commercial source
1
99.5
3
Stated by supplier
8
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
H2O
1
Commercial source
1
99.8
3
Estimated by the compiler
9
InChI=1S/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H
WURBFLDFSFBTLW-UHFFFAOYSA-N
1,2-diphenylethanedione
benzil
dibenzoyl
C14H10O2
1
Commercial source
1
98
2
Estimated by the compiler
10
InChI=1S/C3H6O2/c1-3(4)5-2/h1-2H3
KXKVLQRXCPHEJC-UHFFFAOYSA-N
methyl ethanoate
acetic acid, methyl ester
ethanoic acid, methyl ester
methyl acetate
C3H6O2
1
Commercial source
1
99
2
Estimated by the compiler
11
InChI=1S/C2H3N/c1-2-3/h1H3
WEVYAHXRMPXWCK-UHFFFAOYSA-N
acetonitrile
cyanomethane
ethanenitrile
ethanonitrile
methanecarbonitrile
methyl cyanide
C2H3N
1
Commercial source
1
99
2
Estimated by the compiler
1
1
1
Principal objective of the work
EP
EP
11/7/2016
1
Triple point temperature, K
DSC
Crystal
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Crystal
Liquid
Air at 1 atmosphere
1
542.96
5
1
1.22
2
1
1
Principal objective of the work
EP
EP
10/17/2016
1
Molar enthalpy of transition or fusion, kJ/mol
DSC
Crystal
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Crystal
Liquid
Air at 1 atmosphere
1
56.44
4
1
3.55
3
2
1
Principal objective of the work
EP
EP
10/17/2016
1
Triple point temperature, K
DSC
Crystal
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Crystal
Liquid
Air at 1 atmosphere
1
376.32
5
1
1.22
4
2
1
Principal objective of the work
EP
EP
10/17/2016
1
Molar enthalpy of transition or fusion, kJ/mol
DSC
Crystal
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Crystal
Liquid
Air at 1 atmosphere
1
50.93
4
1
3.21
5
3
1
Principal objective of the work
EP
EP
9/21/2016
1
Triple point temperature, K
DSC
Crystal
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Crystal
Liquid
Air at 1 atmosphere
1
432.22
5
1
1.22
6
3
1
Principal objective of the work
EP
EP
9/21/2016
1
Molar enthalpy of transition or fusion, kJ/mol
DSC
Crystal
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Crystal
Liquid
Air at 1 atmosphere
1
29.63
4
1
1.88
7
6
1
5
1
8
1
Principal objective of the work
EP
EP
11/7/2016
1
Mass density, kg/m3
Vibrating tube method
Liquid
Direct value, X
8
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
1
Amount ratio of solute to solvent
5
Liquid
0.0833
3
2
Amount ratio of solute to solvent
6
Liquid
0.0833
3
3
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
1
293.15
5
1
1310.782
7
1
2.628
1
298.15
5
1
1307.512
7
1
2.622
1
303.15
5
1
1304.176
7
1
2.615
1
308.15
5
1
1300.794
7
1
2.608
1
313.15
5
1
1297.384
7
1
2.601
1
318.15
5
1
1293.928
7
1
2.594
1
323.15
5
1
1290.439
7
1
2.587
8
6
1
5
1
8
1
Principal objective of the work
EP
EP
11/7/2016
1
Viscosity, Pa*s
Concentric cylinders viscometry
Liquid
Direct value, X
8
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
1
Amount ratio of solute to solvent
5
Liquid
0.0833
3
2
Amount ratio of solute to solvent
6
Liquid
0.0833
3
3
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
1
293.15
5
1
0.045461
5
1
0.000484
1
298.15
5
1
0.034646
5
1
0.000369
1
303.15
5
1
0.027063
5
1
0.000289
1
308.15
5
1
0.021593
5
1
0.00023
1
313.15
5
1
0.017538
5
1
0.000187
1
318.15
5
1
0.014457
5
1
0.000154
1
323.15
5
1
0.012087
5
1
0.000129
9
4
1
5
1
8
1
Principal objective of the work
EP
EP
9/21/2016
1
Mass density, kg/m3
Vibrating tube method
Liquid
Direct value, X
8
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
1
Amount ratio of solute to solvent
4
Liquid
0.0909
3
2
Amount ratio of solute to solvent
5
Liquid
0.0909
3
3
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
1
293.15
5
1
1200.75
7
1
2.408
1
298.15
5
1
1197.773
7
1
2.402
1
303.15
5
1
1194.75
7
1
2.396
1
308.15
5
1
1191.71
7
1
2.39
1
313.15
5
1
1188.624
7
1
2.384
1
318.15
5
1
1185.531
7
1
2.378
1
323.15
5
1
1182.4
7
1
2.371
10
4
1
5
1
8
1
Principal objective of the work
EP
EP
9/21/2016
1
Viscosity, Pa*s
Concentric cylinders viscometry
Liquid
Direct value, X
8
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
1
Amount ratio of solute to solvent
4
Liquid
0.0909
3
2
Amount ratio of solute to solvent
5
Liquid
0.0909
3
3
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
1
293.15
5
1
0.015842
5
1
0.000172
1
298.15
5
1
0.013209
5
1
0.000144
1
303.15
5
1
0.011133
5
1
0.000121
1
308.15
5
1
0.009497
4
1
0.000103
1
313.15
5
1
0.008162
4
1
8.9e-05
1
318.15
5
1
0.007074
4
1
7.7e-05
1
323.15
5
1
0.006174
4
1
6.8e-05
11
6
1
4
1
8
1
Principal objective of the work
EP
EP
9/21/2016
1
Mass density, kg/m3
Vibrating tube method
Liquid
Direct value, X
8
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
1
Amount ratio of solute to solvent
4
Liquid
0.0909
3
2
Amount ratio of solute to solvent
6
Liquid
0.0909
3
3
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
1
293.15
5
1
1185.368
7
1
2.377
1
298.15
5
1
1182.98
7
1
2.372
1
303.15
5
1
1180.528
7
1
2.367
1
308.15
5
1
1178.039
7
1
2.362
1
313.15
5
1
1175.504
7
1
2.357
1
318.15
5
1
1172.924
7
1
2.352
1
323.15
5
1
1170.3
7
1
2.347
12
6
1
4
1
8
1
Principal objective of the work
EP
EP
9/21/2016
1
Viscosity, Pa*s
Concentric cylinders viscometry
Liquid
Direct value, X
8
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
1
Amount ratio of solute to solvent
4
Liquid
0.0909
3
2
Amount ratio of solute to solvent
6
Liquid
0.0909
3
3
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
1
293.15
5
1
0.015943
5
1
0.000173
1
298.15
5
1
0.013172
5
1
0.000143
1
303.15
5
1
0.01099
5
1
0.00012
1
308.15
5
1
0.009287
4
1
0.000101
1
313.15
5
1
0.007922
4
1
8.6e-05
1
318.15
5
1
0.006813
4
1
7.5e-05
1
323.15
5
1
0.005902
4
1
6.5e-05
13
7
1
4
1
8
1
Principal objective of the work
EP
EP
9/21/2016
1
Mass density, kg/m3
Vibrating tube method
Liquid
Direct value, X
8
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
1
Amount ratio of solute to solvent
4
Liquid
0.1
3
2
Amount ratio of solute to solvent
7
Liquid
0.1
3
3
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
1
293.15
5
1
1272.692
7
1
2.555
1
298.15
5
1
1270.121
7
1
2.55
1
303.15
5
1
1267.464
7
1
2.544
1
308.15
5
1
1264.743
7
1
2.539
1
313.15
5
1
1261.978
7
1
2.533
1
318.15
5
1
1259.207
7
1
2.527
1
323.15
5
1
1256.42
7
1
2.522
14
7
1
4
1
8
1
Principal objective of the work
EP
EP
9/21/2016
1
Viscosity, Pa*s
Concentric cylinders viscometry
Liquid
Direct value, X
8
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
1
Amount ratio of solute to solvent
4
Liquid
0.1
3
2
Amount ratio of solute to solvent
7
Liquid
0.1
3
3
Pressure, kPa
Liquid
100
1
1
Temperature, K
Liquid
1
293.15
5
1
0.15399
6
1
0.002682
1
298.15
5
1
0.112048
6
1
0.001624
1
303.15
5
1
0.083305
5
1
0.00102
1
308.15
5
1
0.063355
5
1
0.000688
1
313.15
5
1
0.049133
5
1
0.000532
1
318.15
5
1
0.038732
5
1
0.00042
1
323.15
5
1
0.031018
5
1
0.000336
15
10
1
9
1
Principal objective of the work
EP
EP
11/7/2016
1
Mole fraction
Chromatography
9
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
9
1
Temperature, K
Liquid
2
Pressure, kPa
Liquid
1
298.15
5
2
100
1
1
0.148
3
1
0.009
16
11
1
9
1
Principal objective of the work
EP
EP
11/7/2016
1
Mole fraction
Chromatography
9
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Crystal
9
1
Temperature, K
Liquid
2
Pressure, kPa
Liquid
1
298.15
5
2
100
1
1
0.0614
3
1
0.0037