γ-Cyclodextrin

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γ-cyclodextrin
Names
IUPAC name
cyclomaltooctaaose
Systematic IUPAC name
cyclooctaakis-(1→4)-α-D-glucopyranosyl
Other names
Cyclooctaamylose
Cyclooctadextrin
gammadex
ringdex C
Identifiers
3D model (JSmol)
78740
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.037.696 Edit this at Wikidata
E number E458 (thickeners, ...)
UNII
  • InChI=1S/C48H80O40/c49-1-9-33-17(57)25(65)41(73-9)82-34-10(2-50)75-43(27(67)19(34)59)84-36-12(4-52)77-45(29(69)21(36)61)86-38-14(6-54)79-47(31(71)23(38)63)88-40-16(8-56)80-48(32(72)24(40)64)87-39-15(7-55)78-46(30(70)22(39)62)85-37-13(5-53)76-44(28(68)20(37)60)83-35-11(3-51)74-42(81-33)26(66)18(35)58/h9-72H,1-8H2/t9-,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-,43-,44-,45-,46-,47-,48-/m1/s1
    Key: GDSRMADSINPKSL-HSEONFRVSA-N
  • 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(C(C8O)O)OC9C(OC(O2)C(C9O)O)CO)CO)CO)CO)CO)CO)CO)O)O)O
Properties
C48H80O40
Molar mass 1297.128 g·mol−1
Appearance white solid
Density 1.41 g/cm3
Melting point 474 °C (885 °F; 747 K) at fast heating rates, decomposition below 300 °C for conventional heating [1]
23.2 g/100 mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

γ-Cyclodextrin sometimes abbreviated as γ-CD, is an octasaccharide derived from glucose. The α- (alpha), β- (beta), and γ- (gamma) cyclodextrins correspond to six, seven, and eight glucose units, respectively.

Structure

Main article: cyclodextrin § Structure

In γ-cyclodextrin, the eight glucose subunits are linked end to end via α-1,4 linkages. The result has the shape of a tapered cylinder, with 8 primary alcohols on one face and 16 secondary alcohol groups on the other. The exterior surface of cyclodextrins is somewhat hydrophilic whereas the interior core is hydrophobic.

Physical properties

γ-Cyclodextrin exists as a white (colorless) powder or crystals. The density of its hydrate crystal (γCD·14H2O) is 1.41 g/cm3. γ-Cyclodextrin is well soluble in water and dimethyl sulfoxide, poorly soluble in methanol.[2]

Applications

γ-Cyclodextrins has the largest cavity size between natural cyclodextrin, thus, it is well-suited to accommodate larger biomolecules and other guests. For this reason, γ-cyclodextrin is most commonly used as a complexing agent. γ-Cyclodextrin is widely used in medicine, pharmacy, food industry, cosmetics, textiles.

Derivatives

To increase solubility, hydroxypropylated γ-cyclodextrin derivative (HPγCD) is obtained by treating the natural cyclodextrin with propylene oxide, and sulfobutylether γ-cyclodextrin (SBEγCD) by treating the natural CD with 1,4-butane sultone.[3] Sugammadex is the derivative of γ-cyclodextrin applied as a medication.

See also

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. ^ Gamma-cyclodextrin
  3. ^ 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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