Solubility behavior of .beta.-cyclodextrin in water/cosolvent mixtures

Chatjigakis, Alexis K.; Donze, C.; Coleman, Anthony W.; Cardot, Philippe

doi:10.1021/ac00038a022

Cited by 139 publications

(73 citation statements)

References 8 publications

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“…In our experiment the solubility of β-CD in water at 30˚C was determined to be 2.25 g/100 mL (19.8 mM), which is in close agreement with the literature value of 2.30 g/100 mL. 22 Although HPBCD is completely soluble in water up to a concentration of 70% (w/w), a strong increase in the viscosity can be observed for concentrations beyond 50% (w/w). 23 The solubility of cyclodextrins in binary organic/water mixtures is very complex, and usually non-linear.…”

Section: Resultssupporting

confidence: 91%

“…Under elevated temperature conditions, β-cyclodextrin is almost three-times more soluble in acetonitrile/water than a methanol/water mixture, which was previously observed. 22 At sub-zero temperature the change in solubility between both phases is more evident (almost 5 times). If we compare each mixture at different temperatures, the solubility of β-CD in methanol/water and acetonitrile/water is changes 5 and 3 times, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…23 The solubility of cyclodextrins in binary organic/water mixtures is very complex, and usually non-linear. 22 For most of the isocratic separations that involve cyclodextrin additives, the concentration of water should be as high as possible to allow good solubility of such macrocycles in the mobile phases. Therefore, a concentration of organic liquids that is close to the mole fraction of Xs = 0.16 is often used.…”

Section: Resultsmentioning

confidence: 99%

“…2 In some cases the additives solubility significantly changes within a relatively small temperature region. 3 For that reason the effective use of relatively lowsoluble host-guest modifiers, such β-cyclodextrin, at a high concentration and low temperature, is strongly limited, and may even cause column and detector failure, or damage. On the other hand, the separation of complex mixtures using the abovementioned mobile phases may be very effective, particularly at sub-zero temperatures.…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of Methanol-Water and Acetonitrile-Water Binary Mixtures as Eluents for Temperature-dependent Inclusion Chromatography

et al. 2006

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In the present study the solubility of β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin at sub-zero and elevated temperatures (-10 and +30˚C) for a given composition of methanol/water and acetonitrile/water binary mixtures (Xs = 0.16) was studied. Moreover, the freezing temperature profiles of acetonitrile-based chromatographic mobile phases were measured, and the obtained results were compared with data available in the literature. Furthermore, the effect of the macrocycles concentration on the liquid-phase freezing points was determined. The low solubility of native β-cyclodextrin in a methanol/water mixture at sub-zero temperature as well as the non-linear behavior of acetonitrile/water mixtures that were observed concerning the freezing point profile are discussed from a practical point of view.

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Section: Resultssupporting

confidence: 91%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Evaluation of Methanol-Water and Acetonitrile-Water Binary Mixtures as Eluents for Temperature-dependent Inclusion Chromatography

et al. 2006

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“…This product was grounded and washed with a mixture of n-isopropyl alcohol/water (70%, v/v), at 30 °C for 48 h under magnetic stirring, to remove possible free b-CD. 23 Then the solid was allowed to settle and the solvent was discarded. This process was repeated three times.…”

Section: Synthesis Of Pss-b-cd Hybrid Polymermentioning

confidence: 99%

A-βcyclodextrin/siloxane hybrid polymer: synthesis, characterization and inclusion complexes

Abbehausen¹,

Formiga²,

Sabadini³

et al. 2010

J. Braz. Chem. Soc.

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Polímero híbrido derivado de siloxano e b-ciclodextrina (b-CD) foi obtido pela reação de b-CD com g-isocianatopropiltrietoxissilano (IPTS), seguido por reação de hidrólise/condensação, gerando uma resina de polissilsesquioxano modificada por b-CD (PSS-b-CD). PSS-b-CD foi caracterizado por espectroscopia infravermelho e ressonância magnética nuclear de 13 C e 29 Si. Este híbrido é amorfo e termicamente estável até 180 °C. PSS-b-CD pode ser obtido também como filme e sua morfologia foi avaliada por microscopia eletrônica de varredura. A capacidade da b-CD ligada ao polímero em formar complexos de inclusão foi avaliada pela formação de um complexo de b-CD-fenolftaleína, utilizando espectroscopia UV-Vis. Mesmo sem mudanças no pH, a forma vermelha da fenolftaleína se converte na forma incolor quando PSS-b-CD é imerso na solução. Cálculos teóricos (métodos AM1 e DFT) mostram que o complexo é formado pela inclusão do anel fenolato na cavidade da b-CD favorecendo a forma incolor da fenolftaleína por mais de 15 kcal mol -1 .A hybrid polymer derived from siloxane and b-cyclodextrin (b-CD) was obtained by reaction of b-CD with g-isocyanatopropyltriethoxysilane (IPTS), followed by hydrolysis/condensation reactions, generating a b-CD-modified polysilsesquioxane resin (PSS-b-CD). PSS-b-CD hybrid was characterized by infrared spectroscopy and 13 C and 29 Si nuclear magnetic resonance. This hybrid was typically amorphous and thermally stable up to 180 o C. PSS-b-CD was able to form films and its morphology was evaluated by scanning electron microscopy. The capability of b-CD grafted in the hybrid polymer to form inclusion complex was evaluated by the formation of a b-CD-phenolphthalein complex using UV-Vis spectroscopy. Even without changes in pH, the red form of phenolphthalein converts to the colorless one when PSS-b-CD is immersed in the solution. Theoretical calculations (AM1 and DFT methods) show that the complex is formed through the inclusion of the phenolate ring into b-CD cavity, favoring the colorless form of phenolphthalein by more than 15 kcal mol -1 .

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Cucurbiturils, Synthesis and Applications

Mohanty

2015

Encyclopedia of Polymer Science and Technology

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The research on the chemistry of host–guest complexes based on noncovalent interactions involving a macrocyclic host and a guest has seen an upsurge in recent years due to their potential application in metal ion separation, molecular sensors, catalysis, nanomaterials and therapeutics, and other stimuli‐responsive systems. This article provides a brief account of a relatively new class of macrocyclic hosts, cucurbit[ n ]uril (CB n ), their molecular recognition properties with several important guest molecules, and their applications. Along with various synthetic approaches, an environmental friendly ( green ) method to isolate CB n homologues (CB[5–8]) by utilizing imidazolium salts has also been discussed. The noncovalent host–guest assemblies with cucurbiturils bring out a remarkable modulation of the physicochemical properties of the guest molecules such as solubility, stability, aggregation behavior, acidity constants, antibacterial activity, and cytotoxicity. Efforts have also been made to give specific examples of cucurbituril‐encapsulated guest assemblies and discuss their potential applications toward controlled uptake and release of drugs, construction of photofunctional devices, aqueous‐based dye lasers, molecular architectures, gas sensors, stimuli‐responsive hydrogel, chemoselective photoreactions, biological catalytic activity, and inhibition of amyloid fibrillation.

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Solubility behavior of .beta.-cyclodextrin in water/cosolvent mixtures

Cited by 139 publications

References 8 publications

Evaluation of Methanol-Water and Acetonitrile-Water Binary Mixtures as Eluents for Temperature-dependent Inclusion Chromatography

Evaluation of Methanol-Water and Acetonitrile-Water Binary Mixtures as Eluents for Temperature-dependent Inclusion Chromatography

A-βcyclodextrin/siloxane hybrid polymer: synthesis, characterization and inclusion complexes

Cucurbiturils, Synthesis and Applications

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