Antisolvent Crystallization of Polymorphs of <i>L</i>‐Histidine

Punmalee, Neeranuch; Wantha, Lek; Flood, Adrian E.

doi:10.1002/ceat.201700676

Cited by 13 publications

(17 citation statements)

References 25 publications

(29 reference statements)

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“…The obtained photomicrographs of the prepared crystals of forms A and B indicated that the crystals of form A exhibited rod‐like shapes consistent with those reported in previous works , , . The shape of crystals of form B appeared plate‐like like those reported in former works , , .…”

Section: Resultssupporting

confidence: 88%

“…Pure crystals of form A of L ‐his were produced from aqueous solution crystallization by cooling operation at 25 °C as described in previous works , , , . A saturated aqueous solution of L ‐his at 45 °C was prepared at 50 °C and then the solution was cooled rapidly to 10 °C.…”

Section: Methodsmentioning

confidence: 99%

“…In literature, L ‐his is known to crystallize in a metastable polymorph B and a stable polymorph A , , . Kitamura et al , studied the formation and transformation of polymorphs of L ‐his by rapidly cooling aqueous and ethanol‐water solutions.…”

Section: Introductionmentioning

confidence: 99%

“… and Punmalee et al. , studied the effects of solvents on the formation of the polymorphs of L ‐his at the initial stage of the antisolvent crystallization. Ethanol, methanol, acetone, and acetonitrile were selected as antisolvents and water as solvent.…”

Section: Introductionmentioning

confidence: 99%

“…The solubility data of the solute in the solvent‐antisolvent systems is of great importance to study the SMPT in antisolvent crystallization. Solubility data of the stable form A in water‐acetone, water‐ethanol, water‐methanol, water‐acetonitrile, and water‐propanol were reported , , .…”

Section: Introductionmentioning

confidence: 99%

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Influence of Solvents on Solution‐Mediated Polymorphic Transformation of the Polymorphs of L‐Histidine

2019

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Solution-mediated polymorphic transformation (SMPT) of the metastable polymorph B of L-histidine (L-his) into the stable polymorph A in water-antisolvent solutions was performed. Methanol, acetone, and acetonitrile served as antisolvents. The SMPT was studied via nucleated batch antisolvent crystallization process by determining the change of the fraction of the stable polymorph A of L-his in the crystal phase with time during the crystallization process. The fraction of the stable polymorph A of L-his was assessed offline by Raman spectroscopy. The transformation time depended on the fractions of form A obtained at the initial stage of crystallization. The transformation rate of the metastable polymorph B into the stable polymorph A at lower antisolvent volume fraction was faster than at higher antisolvent volume fraction. The transformation time of polymorph B into polymorph A in water-acetonitrile solution was the shortest compared to the other solutions.

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Section: Resultssupporting

confidence: 88%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Influence of Solvents on Solution‐Mediated Polymorphic Transformation of the Polymorphs of L‐Histidine

2019

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Preparation and Characterization of Taxifolin Form II by Antisolvent Recrystallization

Wei

Wang

et al. 2018

Chem Eng & Technol

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To improve the aqueous solubility and dissolution rate of taxifolin, taxifolin form II was successfully prepared through antisolvent recrystallization, in which 1‐butyl‐3‐methylimidazolium tetrafluoroborate and dichloromethane were used as solvent and antisolvent, respectively. The properties of taxifolin form II were characterized by scanning electron microscopy, Fourier transform infrared spectroscopy, X‐ray diffraction, differential scanning calorimetry, solid‐state NMR spectroscopy, the dissolving capability test, and the bioavailability test. The chemical structure of taxifolin form II was not changed, but its morphology and crystalline structure changed during the recrystallization process. Moreover, taxifolin form II showed higher solubility, faster dissolution rate, and better bioavailability than taxifolin form I.

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Experiments and Correlations of the Solubility of γ‐DL‐Methionine in Binary Solvent Mixtures

2020

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Antisolvents increase the supersaturation in the crystallization process which can enhance the product yield. The effect of an antisolvent on the solubility of g-DL-methionine (g-DL-met) in aqueous solution was investigated. The solubility of g-DL-met was measured with various binary solvent mixtures. It improved with higher temperature but decreased with increasing the antisolvent mass fraction. Acetone showed the highest efficiency to reduce the solubility. The solubilities were correlated with the van't Hoff-Jouyban-Acree model and the modified Apelblat-Jouyban-Acree model. Both models fitted to the experimental results with high accuracy. Enthalpy, entropy, and Gibbs free energy of dissolution were determined by van't Hoff analysis. The thermodynamic properties indicated that the dissolution process is endothermic and entropy-driven.

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Antisolvent Crystallization of Polymorphs of L‐Histidine

Cited by 13 publications

References 25 publications

Influence of Solvents on Solution‐Mediated Polymorphic Transformation of the Polymorphs of L‐Histidine

Influence of Solvents on Solution‐Mediated Polymorphic Transformation of the Polymorphs of L‐Histidine

Preparation and Characterization of Taxifolin Form II by Antisolvent Recrystallization

Experiments and Correlations of the Solubility of γ‐DL‐Methionine in Binary Solvent Mixtures

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