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39915

Sigma-Aldrich

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

≥98.0% (TLC)

Synonym(s):

2,6-Di-O-methyl-β-cyclodextrin, Dimethyl β-cyclodextrin

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About This Item

Empirical Formula (Hill Notation):
C56H98O35
CAS Number:
51166-71-3
Molecular Weight:
1331.36
Beilstein:
1679144
MDL number:
MFCD00011616
UNSPSC Code:
12352005
PubChem Substance ID:
57649911
NACRES:
NA.22

Quality Level

100

Assay

≥98.0% (TLC)

optical activity

[α]20/D +158±3°, c = 10% in H2O

impurities

≤3% water

SMILES string

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

InChI key

QGKBSGBYSPTPKJ-UZMKXNTCSA-N

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General description

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

Application

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 and reduced haloperidol by capillary zone electrophoresis.
  • As a component of thermosensitive polyurethane copolymers for their subsequent analysis by gel permeation chromatography (GPC).

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

Other Notes

Complexes are more soluble in aqueous solution than the corresponding complexes of β-cyclodextrin; Stimulation of fatty acid synthesis

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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New thermogelling copolymers composed of heptakis (2, 6-di-O-methyl)-beta-cyclodextrin, poly (propylene glycol), and poly (ethylene glycol)
Yang C, et al.
Journal of Materials Chemistry, 19(22), 3755-3763 (2009)
Effects of cyclodextrins on fatty acid synthesis.
Y Machida et al.
The Journal of biological chemistry, 248(17), 6246-6247 (1973-09-10)
Chiral separation of reduced haloperidol by capillary zone electrophoresis with heptakis (2, 6-di-O-methyl)-beta-cyclodextrin
Wu HL, et al.
Journal of Liquid Chromatography and Related Technologies, 19(10), 1567-1577 (1996)
T Kiss et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 40(4), 376-380 (2010-05-04)
Several beta-cyclodextrin (beta-CD) derivatives have been synthesized recently to improve the physicochemical properties and inclusion capacities of the parent molecule, however, there is limited information available about their cytotoxic effects. In this study we investigated the cytotoxic and hemolytic properties
F Hirayama et al.
Journal of pharmaceutical sciences, 88(10), 970-975 (1999-10-09)
Acetyl groups were introduced to the hydroxyl groups of heptakis(2, 6-di-O-methyl)-beta-cyclodextrin (DM-beta-CyD), and the resulting heptakis(2,6-di-O-methyl-3-O-acetyl)-beta-CyD (DMA-beta-CyD) was evaluated for the inclusion property and hemolytic activity. It was confirmed by means of NMR and mass spectroscopies that in the DMA-beta-CyD
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