α-Cyclodextrin

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Α-Cyclodextrin
Names
IUPAC name
cyclomaltohexaose
Systematic IUPAC name
cyclohexakis-(1→4)-α-D-glucopyranosyl
Other names
Cyclohexaamylose
Cyclohexadextrin
Cyclomaltohexose
α-Cycloamylose
α-Dextrin
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.029.995 Edit this at Wikidata
EC Number
  • 233-007-4
KEGG
UNII
  • InChI=1S/C36H60O30/c37-1-7-25-13(43)19(49)31(55-7)62-26-8(2-38)57-33(21(51)15(26)45)64-28-10(4-40)59-35(23(53)17(28)47)66-30-12(6-42)60-36(24(54)18(30)48)65-29-11(5-41)58-34(22(52)16(29)46)63-27-9(3-39)56-32(61-25)20(50)14(27)44/h7-54H,1-6H2/t7-,8-,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-/m1/s1
    Key: HFHDHCJBZVLPGP-RWMJIURBSA-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](O2)[C@@H]([C@H]7O)O)CO)CO)CO)CO)CO)O)O)O
Properties
C36H60O30
Molar mass 972.846 g·mol−1
Appearance white solid
Melting point 507 °C (945 °F; 780 K) at fast heating rates, decomposition below 300 °C for conventional heating [1]
14.5 g/100 mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

α-Cyclodextrin (alpha-cyclodextrin), sometimes abbreviated as α-CD, is a hexa

saccharide derived from glucose. It is related to the β- (beta) and γ- (gamma) cyclodextrins, which contain seven and eight glucose units, respectively. All cyclodextrins are white, water-soluble solids with minimal toxicity. Cyclodextrins tend to bind other molecules in their quasi-cylindrical, lipophilic interiors. The compound is of wide interest because it exhibits host–guest properties, forming inclusion compounds.[2] This inclusion (and release) behavior leads to applications in medicine.[3]

Structure

Main article: cyclodextrin § Structure

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

Three representations of α-cyclodextrin.

Applications

α-Cyclodextrin is marketed for a range of medical, healthcare, and food and beverage applications. For drug delivery, this cyclodextrin confers aqueous solubility to hydrophobic drugs and stability to labile drugs.[4]

Crystal structure of a rotaxane with an α-cyclodextrin macrocycle.[5]

Synthesis

Cyclodextrins are natural starch-conversion products. For industrial use, they are manufactured by enzymatic degradation from vegetable raw materials, such as corn or potatoes. First, the starch is liquified either by heat treatment or using α-amylase. Then

cyclodextrin glycosyltransferase (CGTase) is added for enzymatic conversion. CGTases produce diverse cyclodextrins. The selectivity of the synthesis can be improved by the addition of specific guests.[3]

See also

References

  1. PMID 36361919
  2. PMID 28462968
    .
  3. ^
    PMID 11848947
    .
  4. ISBN 978-3-527-30673-2
    .
  5. doi:10.1039/b010015n
    .
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