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

Name: Heptakis(2,3,6-tri-<I>O</I>-methyl)-β-cyclodextrin
Brand: SIAL

≥98.0%

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Synonym(s):

TM-β-CD, TM‐β‐CyD, TRIMEB, 2,3,6-Tri-O-methyl-β-cyclodextrin, Trimethyl-β-cyclodextrin

Empirical Formula (Hill Notation):

C₆₃H₁₁₂O₃₅

CAS Number:

55216-11-0

Molecular Weight:

1429.54

Beilstein:

78748

MDL number:

MFCD00010728

PubChem Substance ID:

329757734

NACRES:

NA.22

Quality Level

100

Assay

≥98.0% (TLC)
≥98.0%

form

powder or crystals

optical activity

[α]25/D +157±4°, c = 1% in H₂O

mp

170-178 °C (lit.)

solubility

H₂O: 50 mg/mL, slightly turbid, colorless

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).
In the determination of 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

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Simultaneous measurement of ionic current and fluorescence from single protein pores.

Andrew J Heron et al.

Journal of the American Chemical Society, 131(5), 1652-1653 (2009-01-17)

The ability to simultaneously monitor both the ionic current and fluorescence from membrane channels and pores has the potential to link structural changes with function in such proteins. We present a new method for simultaneously measuring single-channel electrical currents and

Crystal structure of heptakis (2, 3, 6-tri-O-methyl)-beta-cyclodextrin complexes with m-iodophenol and 4-biphenylacetic acid. Guest-induced conformational change of a pyranose ring

Harata K, et al.

Journal of the Chemical Society. Perkin Transactions 1, 7, 1159-1166 (1992)

Combined use of chiral ionic liquid and CD for MEKC: Part II. Determination of binding constants.

Bin Wang et al.

Electrophoresis, 30(16), 2820-2828 (2009-08-20)

A competitive inhibition mechanism is proposed to investigate the interactions among 2,3,6-tri-O-methyl-beta-CD (TM-beta-CD), cationic ionic liquid type surfactants, N-undecenoxy-carbonyl-L-leucinol bromide (L-UCLB) and profens using affinity CE. The apparent binding constant of TM-beta-CD to L-UCLB was estimated by nonlinear and linear

Stabilization of all-trans-retinol by cyclodextrins: a comparative study using HPLC and fluorescence spectroscopy

Semenova EM, et al.

Journal of Inclusion Phenomena and Macrocyclic Chemistry, 44(1-4), 155-158 (2002)

Selective interaction of 2,6-di-O-methyl-β-cyclodextrin and Pluronic F127 micelles leading to micellar rupture: a nuclear magnetic resonance study.

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

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