β-Cyclodextrin

β-Cyclodextrin sometimes abbreviated as β-CD, is a heptasaccharide derived from glucose. The α- (alpha), β- (beta), and γ- (gamma) cyclodextrins correspond to six, seven, and eight glucose units, respectively. β-Cyclodextrin is the most used natural cyclodextrin in marketed medicines.[2] The reason for this lies in the ease of its production and subsequent low price (more than 10,000 tons produced annually with an average bulk price of approximately 5 USD per kg).

β-Cyclodextrin
Names
IUPAC name
cyclomaltoheptaose
Systematic IUPAC name
cycloheptakis-(1→4)-α-D-glucopyranosyl
Other names
Cycloheptaamylose
Cycloheptadextrin
Cyclomaltoheptose
β-Cycloamylose
Schardinger β-Dextrin
betadex
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.028.631
EC Number
  • 233-007-4
E number E459 (thickeners, ...)
KEGG
UNII
  • C(C1C2C(C(C(O1)OC3C(OC(C(C3O)O)OC4C(OC(C(C4O)O)OC5C(OC(C(C5O)O)OC6C(OC(C(C6O)O)OC7C(OC(C(C7O)O)OC8C(OC(O2)C(C8O)O)CO)CO)CO)CO)CO)CO)O)O)O
Properties
C42H70O35
Molar mass 1134.987 g·mol−1
Appearance white solid
Melting point 501 °C (934 °F; 774 K) at fast heating rates, decomposition below 300 °C for conventional heating [1]
1.85 g/100 mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references


Structure
Main article: cyclodextrin § Structure

In β-cyclodextrin, the seven glucose subunits are linked end to end via α-1,4 linkages. The result has the shape of a tapered cylinder, with seven primary alcohols on one face and fourteen secondary alcohol groups on the other. The exterior surface of cyclodextrins is somewhat hydrophilic whereas the interior core is hydrophobic.

Physical properties

β-Cyclodextrin exists as a white (colorless) powder or crystals. The density of its saturated hydrate crystal (βCD·12H2O) is 1.46 g/cm3. β-Cyclodextrin is moderately soluble in water and glycerin; well soluble in dimethyl sulfoxide, dimethylformamide, pyridine, HFIP, and ethylene glycol; and insoluble in ethanol and acetone.[3]

Applications

The cavity diameter of β-cyclodextrins is well-suited for use with molecules the size of various biomolecules. For this reason, β-cyclodextrin is most commonly used as a complexing agent. β-Cyclodextrin is widely used in medicine, pharmacy, food industry, textiles.

Derivatives

While as β-cyclodextrin has rather poor solubility, industry uses its derivatives with much better solubility. Most applied derivatives are: 2-hydroxypropyl-β-cyclodextrin (HPbCD), randomly methylated β-cyclodextrin (RAMEB), and β-cyclodextrin sulfobutyl ether sodium salt (SBEbCD). All these derivatives have solubility more than 500 mg/mL.[4]

References
  1. Gatiatulin, Askar (2022), "Determination of Melting Parameters of Cyclodextrins Using Fast Scanning Calorimetry", Int. J. Mol. Sci., 23 (21): 13120, doi:10.3390/ijms232113120, PMC 9655725, PMID 36361919
  2. Kurkov, Sergey (2013), "Cyclodextrins", Int. J. Pharm., 453 (1): 167–180, doi:10.1016/j.ijpharm.2012.06.055, PMID 22771733
  3. Miranda, Janisse Crestani de (2011), "Cyclodextrins and ternary complexes: technology to improve solubility of poorly soluble drugs", Brazilian Journal of Pharmaceutical Sciences, 47 (4): 665–681, doi:10.1590/S1984-82502011000400003
  4. Jansook, Phatsawee (2018), "Cyclodextrins: structure, physicochemical properties and pharmaceutical applications", Int. J. Pharm., 535 (1–2): 272–284, doi:10.1016/j.ijpharm.2017.11.018, PMID 29138045
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.