Effect of ethanol on crystallization of the polymorphs of L-histidine

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

doi:10.1016/j.jcrysgro.2018.03.019

Cited by 20 publications

(27 citation statements)

References 21 publications

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“…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%

“…Wantha et al. 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.…”

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: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Wantha et al. 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.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

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

2019

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“…Zhu et al [40] indicated that the polymorph nucleation of gestodene in ethanol depends on both the supersaturation and crystallization temperature. Roelands et al [41] and Wantha et al [42] reported that the metastable polymorph increases with increasing supersaturation for the crystallization of L-histidine from aqueous solution with the antisolvent ethanol.…”

Section: Introductionmentioning

confidence: 99%

Modelling of the Polymorph Nucleation Based on Classical Nucleation Theory

Shiau

2019

Crystals

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To elucidate the relative nucleation rates of different polymorphs, a competitive kinetic model is developed based on classical nucleation theory to describe the time evolution of two different polymorphic cluster size distributions controlled by the association and dissociation of the solute molecules during polymorph nucleation. Although there is only one type of the solute molecules, the agglomerated solute clusters are divided into two types-A form and B form, which resemble the structures and morphologies of the different mature polymorphs and eventually lead to the formation of two polymorphic crystals. A dissociation kernel is incorporated into the proposed model to account for gradual dissolution of the solute clusters smaller than a critical nucleus size due to the thermodynamic instability. By fitting the experimental induction period data and the final measured weight fractions of eflucimibe polymorphs with the proposed model, the association and dissociation rate constants for two polymorphs are determined. The developed model is satisfactory to explain the competitive mechanism of polymorph nucleation for eflucimibe that B form dominates at higher supersaturation while A form dominates at lower supersaturation. The results also indicate that A form is more stable than B form with a transition energy of 3.1 kJ/mole at 35 • C.

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Passive Polarized Light Guiding and Thermally Induced Visible Fluorescence in Histidine Microstructures with Optical Switching Function

Handelman

Lapsker

Jacob

et al. 2020

Adv Funct Materials

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The increasing interest in implantable medical devices that incorporate photonic components has accelerated the search for new, biocompatible optical materials at micro‐ and nano‐scale. This work proposes use of the polar amino acid L‐histidine as a candidate for bio‐photonic devices. L‐histidine is self‐assembled into diverse solid‐state crystallized microstructures, one of which—the elongated hexagonal microplate—is shown to have passive waveguiding capability of polarized light. The interaction of polarized light with histidine microplates having different orientations and thicknesses is studied from Stokes parameters and Mueller matrix. The linear birefringence of histidine microplates is estimated by using the theory of generalized Jones matrix for biaxial crystals. Visible fluorescence in heated histidine microplates is discovered and its origin is discussed. The phenomenon of passive waveguiding capability of polarized light by such an elongated hexagonal microplate means that the microplate can be used as a part of an optical switch. The findings show that besides the known chemical and biological characteristics of the amino acid histidine, it also has optical properties that can be exploited in multifunctional biophotonic applications, such as waveguides, polarizers, interconnects, and light sources.

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Effect of ethanol on crystallization of the polymorphs of L-histidine

Cited by 20 publications

References 21 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

Modelling of the Polymorph Nucleation Based on Classical Nucleation Theory

Passive Polarized Light Guiding and Thermally Induced Visible Fluorescence in Histidine Microstructures with Optical Switching Function

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