β-Cyclodextrin

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
CAS Number	7585-39-9 (hydrate) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:495055;
ChEMBL	ChEMBL415690;
ChemSpider	10469496;
DrugBank	DB03995;
ECHA InfoCard	100.028.631
EC Number	233-007-4;
E number	E459 (thickeners, ...)
KEGG	C13183;
PubChem CID	444041;
UNII	JV039JZZ3A (hydrate) ;
CompTox Dashboard (EPA)	DTXSID1020358 ;
	SMILES 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
Chemical formula	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 260 °C for conventional heating
Solubility in water	18.5 g/L
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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).

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

β-Cyclodextrin is widely used in medicine, pharmacy, food industry, textiles. Its molecules can accommodate various biomolecules and hence are also used as a complexing agent. Hydrophobic forms of β- CD have been used as sustained release drug carriers. In addition to improving the solubility of compounds, complexation with cyclodextrin has been used to improve the stability of many drugs by inclusion of the compound and protecting certain functional groups from degradation.^[4]

Derivatives

β-cyclodextrin has relatively low solubility in water, and hence industry uses its derivatives, such as 2-hydroxypropyl-β-cyclodextrin (HPbCD), randomly methylated β-cyclodextrin (RAMEB), and β-cyclodextrin sulfobutyl ether sodium salt (SBEbCD).^[5]

References

^ 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
^ Kurkov, Sergey (2013), "Cyclodextrins", Int. J. Pharm., 453 (1): 167–180, doi:10.1016/j.ijpharm.2012.06.055, PMID 22771733
^ 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
^ Pharmatech-rx (2024-07-28). "Cyclodextrin - Application, Types and Properties of Cyclodextrin". Pharmatech. Retrieved 2024-08-05.
^ 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

[Gatiatulin_2022_IJMS-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

[Kurkov-Loftsson-2] Kurkov, Sergey (2013), "Cyclodextrins", Int. J. Pharm., 453 (1): 167–180, doi:10.1016/j.ijpharm.2012.06.055, PMID 22771733

[Miranda-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] Pharmatech-rx (2024-07-28). "Cyclodextrin - Application, Types and Properties of Cyclodextrin". Pharmatech. Retrieved 2024-08-05.

[Jansook-5] 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

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