Polymorphism in β-cyclodextrin–benzoic acid inclusion complex: a kinetically controlled crystal growth according to the Ostwald’s rule

Aree, Thammarat; Chaichit, Narongsak; Engkakul, Chainarong

doi:10.1016/j.carres.2008.06.032

Cited by 16 publications

(15 citation statements)

References 28 publications

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“…Actually, the kinetic behavior of polymorphic nucleation of various systems (e.g., biominerals and drug materials ) often follows this rule. For example, a metastable vaterite form crystallizes faster than the more stable calcite in CaCO 3 .…”

Section: Elementary Processes Of Crystallization and Transformation Omentioning

confidence: 97%

External factors affecting polymorphic crystallization of lipids

Sato

Bayés‐García

Calvet

et al. 2013

Euro J Lipid Sci & Tech

121

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Many physical properties (e.g., hardness, texture, rheology, and spreadability) of lipid-based products largely depend on the extent of crystallization and transformation of lipids, and their network formation. Therefore, many studies have focused on controlling the crystallization of lipids in order to determine the functionality of lipid crystals. Both internal and external factors greatly affect the processes of lipid crystallization. The most important internal factors are polymorphism, which depends on variation in fatty acid moieties, and the composition or blending of different lipid materials. Important external factors are thermal treatment, additives, application of shear, sonication, and pressure. This paper briefly reviews recent advances in research on these external factors. We discuss the results by considering the relationships between external factors and thermodynamics, as well as kinetic properties of the crystallization and transformation of polymorphic forms of lipid crystals.

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Section: Elementary Processes Of Crystallization and Transformation Omentioning

confidence: 97%

External factors affecting polymorphic crystallization of lipids

Sato

Bayés‐García

Calvet

et al. 2013

Euro J Lipid Sci & Tech

121

View full text Add to dashboard Cite

show abstract

“…However, it turned out that PCAC and β-CD co-crystallized to yield a thermodynamically stable adduct in the single-crystalline state. Similarly, benzoic acid with pKa = 4.2 complexed with β-CD in solution [63] and the β-CD-benzoic acid complex existed in two crystal forms [64,65]. In the crystal structure of the β-CD-PCAC complex, the bond distances C7D=O3D, 1.226(6) Å and C7D-O4D, 1.307(6) Å indicated the structure of benzoic group for net charge balance of the stable complex.…”

Section: Dft Full-geometry Optimizationmentioning

confidence: 99%

β-Cyclodextrin Inclusion Complexes with Catechol-Containing Antioxidants Protocatechuic Aldehyde and Protocatechuic Acid—An Atomistic Perspective on Structural and Thermodynamic Stabilities

Aree

2021

Molecules

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Protocatechuic aldehyde (PCAL) and protocatechuic acid (PCAC) are catechol derivatives and have broad therapeutic effects associated with their antiradical activity. Their pharmacological and physicochemical properties have been improved via the cyclodextrin (CD) encapsulation. Because the characteristics of b-CD inclusion complexes with PCAL (1) and PCAC (2) are still equivocal, we get to the bottom of the inclusion complexation by an integrated study of single-crystal X-ray diffraction and DFT full-geometry optimization. X-ray analysis unveiled that PCAL and PCAC are nearly totally shielded in the b-CD wall. Their aromatic rings are vertically aligned in the b-CD cavity such that the functional groups on the opposite side of the ring (3,4-di(OH) and 1-CHO/1-COOH groups) are placed nearby the O6–H and O2–H/O3–H rims, respectively. The preferred inclusion modes in 1 and 2 help to establish crystal contacts of OH×××O H-bonds with the adjacent b-CD OH groups and water molecules. By contrast, the DFT-optimized structures of both complexes in the gas phase are thermodynamically stable via the four newly formed host–guest OH⋯O H-bonds. The intermolecular OH×××O H-bonds between PCAL/PCAC 3,4-di(OH) and b-CD O6–H groups, and the shielding of OH groups in the b-CD wall help to stabilize these antioxidants in the b-CD cavity, as observed in our earlier studies. Moreover, PCAL and PCAC in distinct lattice environments are compared for insights into their structural flexibility.

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“…1 In addition, the kinetic properties of crystallization and structural transformation are important, particularly for the application of polymorphic crystal systems in pharmaceutical, biomedical, food technology, and other applications 2 . As for the crystallization of different polymorphic forms, the Ostwald step rule [3][4][5][6] has been used for macroscopic estimation of the behavior of multiple polymorphic forms when they are crystallized from vapor, solution, and melt phases. This rule dictates that less stable polymorphic forms crystallize much faster than more stable forms when the driving force for crystallization takes place under certain values of supersaturation and supercooling and less stables forms transform to more stable forms after the crystallization.…”

Section: Introductionmentioning

confidence: 99%

In situ synchrotron radiation X-ray diffraction study of crystallization kinetics of polymorphs of 1,3-dioleoyl-2-palmitoyl glycerol (OPO)

et al. 2011

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We examined the influence of kinetics on the polymorphic behavior of 1,3-dioleoyl-2-palmitoyl glycerol (OPO), a triacylglycerol (TAG) present in natural oils such as olive oil and human breast milk. Pure OPO was heated at 15ºC• min-1 in all cases. The polymorphic crystallization of OPO was studied at different cooling rates (15º, 2º, 1º, and 0.5ºC• min-1), and the dynamic polymorphic transformations were characterized on heating by simultaneously using Differential Scanning Calorimetry (DSC) and Synchrotron Radiation X-Ray Diffraction (SR-XRD) with smallangle X-ray diffraction (SAXD) and wide-angle X-ray diffraction (WAXD). Thermo-optical Microscopy (TOM) was also used in order to observe the polymorphic transitions. Polymorphic forms of OPO were identified and characterized. As the cooling rate decreased, more stable forms crystallized, not following the Ostwald step rule, although in most cases concurrent crystallization occurred and the whole process was highly complex.

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Polymorphism in β-cyclodextrin–benzoic acid inclusion complex: a kinetically controlled crystal growth according to the Ostwald’s rule

Cited by 16 publications

References 28 publications

External factors affecting polymorphic crystallization of lipids

External factors affecting polymorphic crystallization of lipids

β-Cyclodextrin Inclusion Complexes with Catechol-Containing Antioxidants Protocatechuic Aldehyde and Protocatechuic Acid—An Atomistic Perspective on Structural and Thermodynamic Stabilities

In situ synchrotron radiation X-ray diffraction study of crystallization kinetics of polymorphs of 1,3-dioleoyl-2-palmitoyl glycerol (OPO)

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