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51707

Sigma-Aldrich

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

≥98.0%

Synonym(s):

TM-β-CD, TM‐β‐CyD, TRIMEB, 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/REAXYS Number:
78748
MDL number:
MFCD00010728
UNSPSC Code:
12352005
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

functional group

ether

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH1782
BCCF4923
BCCF1200
BCCC3169
BCCB4139

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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
Hiroko F Kasai et al.
Chemical & pharmaceutical bulletin, 53(10), 1270-1276 (2005-10-06)
Separation of the enantiomers of each of three different racemates, neutral rac-alpha-tetralol, acidic rac-2-phenylpropionic acid, and basic rac-1-phenylethylamine, using subcritical and supercritical fluid chromatography with two different chiral stationary phases, heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin (Sumichiral OA-7500 column) and tris(3,5-dimethylphenylcarbamate) of amylose (Chiralpak AD-H
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
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
P Andrighetto et al.
Electrophoresis, 21(12), 2384-2389 (2000-08-12)
The water soluble 5-p-aminophenyl)-10,15,20-tris(p-sulfonatophenyl) porphyrin, 4, acts as an extremely efficient chromogenic reagent for the detection of very low amounts of nitrites. The amino group of porphyrin 4 reacts smoothly with nitrite in acidic conditions 0.2 M HCl) producing the
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