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

Solubility of the Proteinogenic a-Amino Acids in Water, Ethanol, and Ethanol-Water Mixtures

Bowden, Nathan A., Sanders, Johan P.M., Bruins, Marieke E.
J. Chem. Eng. Data 2018, 63, 3, 488-497
ABSTRACT
The addition of organic solvents to a-amino acids in aqueous solution could be an effective method in crystallization. We reviewed the data available on the effects of ethanol on the solubility of a-amino acids. The solubility of L-cysteine in water, the solubility of L-alanine, L-proline, L-arginine, L-cysteine, L-lysine and L-methionine in water and ethanol mixtures and the solubility of L-alanine, L-proline, L-arginine, L-cysteine, L-lysine, Lmethionine, L-asparagine, L-glutamine, L-histidine and L-leucine in pure ethanol systems were measured and are published here for the first time. The impact on the solubility of amino acids that can convert in solution, L-glutamic acid and L-cysteine, was studied. At lower concentrations, only the ninhydrin method and the UPLC method yield reliable results. In the case of a-amino acids that convert in solution, only the UPLC method was able to discern between the different a-amino acids and yields reliable results. Our results demonstrate that a- amino acids with similar physical structures have similar changes in solubility in mixed water/ethanol mixtures. The solubility of L-tryptophan increased at moderate ethanol concentrations.
Compounds
# Formula Name
1 H2O water
2 C2H6O ethanol
3 C2H5NO2 2-aminoacetic acid
4 C3H7NO2 (S)-2-aminopropanoic acid
5 C6H14N4O2 L-arginine
6 C4H7NO4 L-aminosuccinic acid
7 C3H7NO2S (R)-2-amino-3-mercaptopropanoic acid
8 C5H9NO4 L-glutamic acid
9 C5H10N2O3 L-glutamine
10 C6H9N3O2 L-histidine
11 C6H13NO2 L-leucine
12 C6H14N2O2 L-lysine
13 C5H11NO2S L-methionine
14 C9H11NO2 L-phenylalanine
15 C5H9NO2 L-proline
16 C11H12N2O2 L-tryptophan
17 C9H11NO3 3-(p-hydroxyphenyl)-L-alanine
18 C4H8N2O3 L-asparagine
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
  • 2
  • 3
  • Mole fraction - 3 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Chromatography
  • 1
  • POMD
  • 1
  • 2
  • 4
  • Mole fraction - 4 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • Chromatography
  • 5
  • POMD
  • 1
  • 2
  • 5
  • Mole fraction - 5 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 5
  • gravimetric
  • 5
  • POMD
  • 1
  • 2
  • 6
  • Mole fraction - 6 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • Chromatography
  • 1
  • POMD
  • 1
  • 2
  • 7
  • Mole fraction - 7 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 7
  • gravimetric
  • 5
  • POMD
  • 1
  • 2
  • 8
  • Mole fraction - 8 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 8
  • Chromatography
  • 6
  • POMD
  • 1
  • 2
  • 9
  • Mole fraction - 9 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 9
  • Chromatography
  • 1
  • POMD
  • 1
  • 2
  • 10
  • Mole fraction - 10 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 10
  • Chromatography
  • 1
  • POMD
  • 1
  • 2
  • 11
  • Mole fraction - 11 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 11
  • Chromatography
  • 1
  • POMD
  • 1
  • 2
  • 12
  • Mole fraction - 12 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 12
  • gravimetric
  • 4
  • POMD
  • 1
  • 2
  • 13
  • Mole fraction - 13 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 13
  • gravimetric
  • 5
  • POMD
  • 1
  • 2
  • 14
  • Mole fraction - 14 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 14
  • gravimetric
  • 4
  • POMD
  • 1
  • 2
  • 15
  • Mole fraction - 15 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 15
  • gravimetric
  • 4
  • POMD
  • 1
  • 2
  • 16
  • Mole fraction - 16 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 16
  • gravimetric
  • 5
  • POMD
  • 1
  • 2
  • 17
  • Mole fraction - 17 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 17
  • gravimetric
  • 5
  • POMD
  • 1
  • 2
  • 18
  • Mole fraction - 18 ; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 18
  • Chromatography
  • 1
  • POMD
  • 2
  • 3
  • Mole fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Chromatography
  • 1
  • POMD
  • 2
  • 4
  • Mole fraction - 4 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • Chromatography
  • 1
  • POMD
  • 1
  • 5
  • Mole fraction - 5 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 5
  • gravimetric
  • 1
  • POMD
  • 2
  • 5
  • Mole fraction - 5 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 5
  • gravimetric
  • 1
  • POMD
  • 2
  • 6
  • Mole fraction - 6 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • Chromatography
  • 1
  • POMD
  • 1
  • 7
  • Mole fraction - 7 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 7
  • gravimetric
  • 1
  • POMD
  • 2
  • 7
  • Mole fraction - 7 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 7
  • gravimetric
  • 1
  • POMD
  • 1
  • 8
  • Mole fraction - 8 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 8
  • Chromatography
  • 1
  • POMD
  • 2
  • 8
  • Mole fraction - 8 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 8
  • Chromatography
  • 1
  • POMD
  • 2
  • 9
  • Mole fraction - 9 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 9
  • Chromatography
  • 1
  • POMD
  • 2
  • 10
  • Mole fraction - 10 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 10
  • Chromatography
  • 1
  • POMD
  • 2
  • 11
  • Mole fraction - 11 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 11
  • Chromatography
  • 1
  • POMD
  • 2
  • 12
  • Mole fraction - 12 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 12
  • gravimetric
  • 1
  • POMD
  • 1
  • 13
  • Mole fraction - 13 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 13
  • gravimetric
  • 1
  • POMD
  • 2
  • 13
  • Mole fraction - 13 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 13
  • gravimetric
  • 1
  • POMD
  • 2
  • 14
  • Mole fraction - 14 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 14
  • gravimetric
  • 1
  • POMD
  • 2
  • 15
  • Mole fraction - 15 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 15
  • gravimetric
  • 1
  • POMD
  • 1
  • 16
  • Mole fraction - 16 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 16
  • gravimetric
  • 1
  • POMD
  • 2
  • 16
  • Mole fraction - 16 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 16
  • gravimetric
  • 1
  • POMD
  • 1
  • 17
  • Mole fraction - 17 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 17
  • gravimetric
  • 1
  • POMD
  • 2
  • 17
  • Mole fraction - 17 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 17
  • gravimetric
  • 1
  • POMD
  • 2
  • 18
  • Mole fraction - 18 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 18
  • Chromatography
  • 2