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H4645

Sigma-Aldrich

Heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin

≥90%

Synonym(s):

2,3,6-Tri-O-methyl-β-cyclodextrin, Trimethyl-β-cyclodextrin

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About This Item

Empirical Formula (Hill Notation):
C63H112O35
CAS Number:
55216-11-0
Molecular Weight:
1429.54
Beilstein:
78748
MDL number:
MFCD00010728
UNSPSC Code:
12352005
PubChem Substance ID:
24895649
NACRES:
NA.22

Assay

≥90%

form

powder

technique(s)

electrophoresis: suitable

mp

170-178 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C63H112O35/c1-64-22-29-36-43(71-8)50(78-15)57(85-29)93-37-30(23-65-2)87-59(52(80-17)44(37)72-9)95-39-32(25-67-4)89-61(54(82-19)46(39)74-11)97-41-34(27-69-6)91-63(56(84-21)48(41)76-13)98-42-35(28-70-7)90-62(55(83-20)49(42)77-14)96-40-33(26-68-5)88-60(53(81-18)47(40)75-12)94-38-31(24-66-3)86-58(92-36)51(79-16)45(38)73-10/h29-63H,22-28H2,1-21H3/t29-,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-,57-,58-,59-,60-,61-,62-,63-/m1/s1

InChI key

DSDAICPXUXPBCC-MWDJDSKUSA-N

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General description

Heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin is a β-cyclodextrin derivative that finds potential use in pharmaceutical, food and cosmetic applications. Its attractive features include: the non-polar cavity desirable for its use as a molecular host for a wide range of molecules and its affinity for organic compounds in solution as well as crystalline phases.

Application

Heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin may be used:
  • To investigate the crystal structure of its complexes with m-iodophenol, 4-biphenylacetic acid and (R)- and (S)-flurbiprofen by X-ray analysis.
  • To study the candidature of its complex with vitamin A for potential application as a drug delivery system for ophthalmic applications by high sensitivity fluorescence spectrometry and high pressure liquid chromatography (HPLC) techniques.
  • In the determination of the analyte composition in commercial samples by HPLC coupled to mass spectrometry (MS).

Chiral additive in liquid chromatography for enantiomer resolution. Chiral separation of basic drug substances by capillary electrophoresis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Franca Castiglione et al.
The journal of physical chemistry. B, 115(29), 9005-9013 (2011-06-15)
The triblock-copolymer poly(ethylene oxide)-poly(propyleneoxide)-poly(ethylene oxide) (PEO-PPO-PEO), referred to as Pluronic, is widely studied for its unique aggregation properties and its applications in drug delivery and targeting. In previous studies [Dreiss, C. A.; et al. Soft Matter 2009, 5, 1888-1896], we
K Payer et al.
Biomedical chromatography : BMC, 9(3), 135-139 (1995-05-01)
The separation efficiency of a capillary column coated with (2,3,6-tri-O-methyl)-beta-cyclodextrin was determined at the temperature and flow rate ranges of 80-120 degrees C and 0.3-1.5 mL/min respectively using (+) and (-) cis-permethrinic acid methylesters as test compounds. The dependence of
Alessandra Ammazzalorso et al.
Journal of chromatography. A, 1088(1-2), 110-120 (2005-09-01)
The enantiomeric separation of gemfibrozil chiral analogues was performed by capillary zone electrophoresis (CZE). Resolution of the enantiomers was achieved using heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin (TM-beta-CD) as chiral selector dissolved into a buffer solution. In order to optimize the separation conditions, type, pH
Koji Kano et al.
Journal of the American Chemical Society, 125(35), 10625-10634 (2003-08-28)
A new methodology for preparing heteroporphyrin arrays in aqueous solution has been presented. The present method is based on the extremely strong ability of heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin (TMe-beta-CD) to include 5,10,15,20-tetrakis(p-substituted-phenyl)porphyrins (Por) affording trans-type 1:2 complexes of the porphyrins and TMe-beta-CD. Two
María Castro-Puyana et al.
Electrophoresis, 27(4), 887-895 (2006-01-18)
The four stereoisomers of itraconazole were resolved for the first time by EKC using a CD as chiral selector. A study on the enantiomeric separation ability of different neutral CDs was carried out. Heptakis-2,3,6-tri-O-methyl-beta-CD was shown to provide the highest
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