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Merck
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Documenti fondamentali

H0513

Sigma-Aldrich

Heptakis(2,6-di-O-methyl)-β-cyclodextrin

Sinonimo/i:

DM-β-CD, DM‐β‐CyD, heptakis-(2,6-O-Dimethyl)-β-cyclodextrin, 2,6-Di-O-methyl-β-cyclodextrin, Dimethyl β-cyclodextrin

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About This Item

Formula empirica (notazione di Hill):
C56H98O35
Numero CAS:
Peso molecolare:
1331.36
Beilstein:
1679144
Numero MDL:
Codice UNSPSC:
12352005
ID PubChem:
NACRES:
NA.22

Origine biologica

synthetic

Livello qualitativo

Stato

powder

Stringa SMILE

COC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](OC)[C@H](O[C@@H]3COC)O[C@H]4[C@H](O)[C@@H](OC)[C@H](O[C@@H]4COC)O[C@H]5[C@H](O)[C@@H](OC)[C@H](O[C@@H]5COC)O[C@H]6[C@H](O)[C@@H](OC)[C@H](O[C@@H]6COC)O[C@H]7[C@H](O)[C@@H](OC)[C@H](O[C@@H]7COC)O[C@H]8[C@H](O)[C@@H](OC)[C@H](O[C@@H]8COC)O[C@H]1[C@H](O)[C@H]2OC

InChI

1S/C56H98O35/c1-64-15-22-36-29(57)43(71-8)50(78-22)86-37-23(16-65-2)80-52(45(73-10)30(37)58)88-39-25(18-67-4)82-54(47(75-12)32(39)60)90-41-27(20-69-6)84-56(49(77-14)34(41)62)91-42-28(21-70-7)83-55(48(76-13)35(42)63)89-40-26(19-68-5)81-53(46(74-11)33(40)61)87-38-24(17-66-3)79-51(85-36)44(72-9)31(38)59/h22-63H,15-21H2,1-14H3/t22-,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-,49-,50-,51-,52-,53-,54-,55-,56-/m1/s1
QGKBSGBYSPTPKJ-UZMKXNTCSA-N

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Descrizione generale

Heptakis(2,6-di-O-methyl)-β-cyclodextrin is a hydrophilic derivative of cyclodextrin that possesses the ability to effectively dissolve lipophilic drugs like steroid hormones, vitamins A, E, and K, etc. It can be utilized to increase the dissolution and bioavailability of weakly water-soluble pharmaceutical compounds.

Applicazioni

Heptakis(2,6-di-O-methyl)-β-cyclodextrin may be used:
  • To measure the equilibrium constant of its complexes with various enantiomeric pairs of chiral nitroxides by electron paramagnetic resonance (EPR) spectroscopy.
  • To study the crystal structure of its complex with n-butyl acrylate and isobornyl acrylate using X-ray diffraction (XRD).
  • As a chiral selector to resolve amphetamine related drugs by capillary zone electrophoresis.

Reactant involved in:
  • Physicochemical studies of inclusion complexes
  • Probing diffusion and single molecule interactions with reconstituted membrane proteins
  • Interactions with micelles causing micellar rupture
  • Studying cellular transport, used as a cell penetration enhancer
  • Physicochemical and biopharmaceutical improvement of drugs particularly with solubilization and stability
  • Interactions with cholesterol

Qualità

Impurities are over-methylated homologs, primarily hexakis(2,6-di-O-methyl)-(2,3,6-tri-O-methyl)-β-cyclodextrin.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


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Z Aigner et al.
Journal of pharmaceutical and biomedical analysis, 57, 62-67 (2011-09-17)
The steps of formation of an inclusion complex produced by the co-grinding of gemfibrozil and dimethyl-β-cyclodextrin were investigated by differential scanning calorimetry (DSC), X-ray powder diffractometry (XRPD) and Fourier transform infrared (FTIR) spectroscopy with curve-fitting analysis. The endothermic peak at
Fernanda Pérez-Cruz et al.
Bioorganic & medicinal chemistry, 17(13), 4604-4611 (2009-05-26)
Four different 5-nitroindazole derivatives (1-4) and its inclusion with Heptakis(2,6-di-O-methyl)-beta-cyclodextrin (DMbetaCD) were investigated. The stoichiometric ratios and stability constants describing the extent of formation of the complexes were determined by phase-solubility measurements obtaining in all cases a type-A(L) diagram. Also
Michelle Amoako-Tuffour et al.
Acta pharmaceutica (Zagreb, Croatia), 59(4), 395-405 (2009-11-19)
The potential for nasal delivery of losartan, a drug with poor oral bioavailability, was investigated using Calu-3 cells. Epithelial permeation of the drug with or without dimethyl-beta-cyclodextrin (DM-beta-CD) and glycocholate was investigated. Possible transport mechanism of the compound and epithelial
Kanokthip Boonyarattanakalin et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 47(4), 752-758 (2012-08-28)
The inclusion complexes of highly potent anti-HIV agent, UC781, with β-cyclodextrin (βCD), 2,6-dimethyl-β-cyclodextrin (MβCD), and 2-hydroxypropyl-β-cyclodextrin (HPβCD) in aqueous solution were investigated by molecular dynamics simulations. Simulations show that the phenyl ring of UC781 is trapped inside CD cavities, while
Shaimaa M Badr-Eldin et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 70(3), 819-827 (2008-07-29)
The aim of this work was to investigate the inclusion complexation between tadalafil, a practically insoluble selective phosphodiesterase-5 inhibitor (PDE5), and two chemically modified beta-cyclodextrins: hydroxypropyl-beta-cyclodextrin (HP-beta-CD) and heptakis-[2,6-di-O-methyl]-beta-cyclodextrin (DM-beta-CD), in comparison with the natural beta-cyclodextrin (beta-CD) in order to

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