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β-Cyclodextrin

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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 Edit this at Wikidata
EC Number
  • 233-007-4
E number E459 (thickeners, ...)
KEGG
UNII
  • InChI=1S/C42H70O35/c43-1-8-29-15(50)22(57)36(64-8)72-30-9(2-44)66-38(24(59)17(30)52)74-32-11(4-46)68-40(26(61)19(32)54)76-34-13(6-48)70-42(28(63)21(34)56)77-35-14(7-49)69-41(27(62)20(35)55)75-33-12(5-47)67-39(25(60)18(33)53)73-31-10(3-45)65-37(71-29)23(58)16(31)51/h8-63H,1-7H2/t8-,9-,10-,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-/m1/s1
    Key: WHGYBXFWUBPSRW-FOUAGVGXSA-N
  • C([C@@H]1[C@@H]2[C@@H]([C@H]([C@H](O1)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5O)O)O[C@@H]6[C@H](O[C@@H]([C@@H]([C@H]6O)O)O[C@@H]7[C@H](O[C@@H]([C@@H]([C@H]7O)O)O[C@@H]8[C@H](O[C@H](O2)[C@@H]([C@H]8O)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 260 °C for conventional heating [1]
18.5 g/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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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

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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] It has an optical rotation of [α]D/25 + 160° to + 164° (1 % solution) [4]

Applications

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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.[5] β-Cyclodextrin is also beginning to be used in environmental chemistry. Its unique structure allows it to form inclusion complexes with various pollutants (primarily tested in aqueous environments) and decrease the concentration of the pollutant. [6]

Inclusion Complexes

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β-Cyclodextrin can form inclusion complexes where molecules including organic pollutants, pesticides, pharmaceuticals, and hydrocarbons can be trapped within the cavity of the β-Cyclodextrin molecule through non-covalent bonds. This property of forming inclusion complexes can be utilized in removing pollutants from water.[7]

β-Cyclodextrin can be modified through crosslinking β-cyclodextrin and linecaps to increase the materials, including the uptake of certain metals, that can be trapped within the molecules cavity.[8]

Derivatives

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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).[9]

History

[edit]

β-cyclodextrin (along with α-cyclodextrin) was first discovered in 1891 by Antoine Villers who studied enzymatic degradation of potato starch in bacteria. Villers first gave them the name “cellulosines” due to their similar properties to cellulose. Later Franz Schardinger renamed these two compounds dextrins leading to the modern name cyclodextrin. Karl Freudenberg and his co-workers, in 1939, published a full description of the two separated compounds, and it wasn't until 1954 when there was a focus on separating and purifying cyclodextrins naturally and their guest inclusion complexes by Friedrich Cramer. [10]

See also

[edit]

References

[edit]
  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, hdl:10316/109986
  4. ^ PubChem (2025), "Beta-Cyclodextrin", PubChem, U.S. National Library of Medicine, retrieved 2025-11-15
  5. ^ Pharmatech-rx (2024-07-28). "Cyclodextrin - Application, Types and Properties of Cyclodextrin". Pharmatech. Retrieved 2024-08-05.
  6. ^ Erdös, Máté; Hartkamp, Remco; Vlugt, Thijs J.H.; Moultos, Othonas A. (2020), "Inclusion Complexation of Organic Micropollutants with Beta-Cyclodextrin", The Journal of Physical Chemistry B, 124 (7): 1218–1228, Bibcode:2020JPCB..124.1218E, doi:10.1021/acs.jpcb.9b10122, PMC 7037149, PMID 31976678{{citation}}: CS1 maint: multiple names: authors list (link)
  7. ^ Urooj, T.; Mishra, M.; Pandey, S. (2024), "Unlocking Environmental Solutions: A Review of Cyclodextrins in Pollutant Removal", Discover Environment, 2 (1) 65: 1–3, Bibcode:2024DiEnv...2...65U, doi:10.1007/s44274-024-00090-w, retrieved 2025-11-15{{citation}}: CS1 maint: multiple names: authors list (link)
  8. ^ Pedrazzo, Alberto Rubin; Smarra, Alessandra; Caldera, Fabrizio; Musso, Giorgia; Dhakar, Nilesh Kumar; Cecone, Claudio; Hamedi, Asma; Corsi, Ilaria; Trotta, Francesco (2019), "Eco-Friendly Beta-Cyclodextrin and Linecaps Polymers for the Removal of Heavy Metals", Polymers, 11 (10): 1658, doi:10.3390/polym11101658, PMC 6835710, PMID 31614648{{citation}}: CS1 maint: multiple names: authors list (link)
  9. ^ 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
  10. ^ Poulson, Benjamin Gabriel; Alsulami, Qana A.; Sharfalddin, Abeer; El Agammy, Emam F.; Mouffouk, Fouzi; Emwas, Abdul-Hamid; Jaremko, Lukasz; Jaremko, Mariusz (2022), "Cyclodextrins: Structural, Chemical, and Physical Properties, and Applications", Polysaccharides, 3 (1): 1–31, doi:10.3390/polysaccharides3010001{{citation}}: CS1 maint: multiple names: authors list (link)
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