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51707

Sigma-Aldrich

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

≥98.0%

Sinónimos:

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

Fórmula empírica (notación de Hill):
C63H112O35
Número de CAS:
55216-11-0
Peso molecular:
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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Certificados de análisis (COA)

Lot/Batch Number
BCCM3991
BCCJ9040
BCCH1782
BCCF4923
BCCF1200

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Characterization of Crystalline Complexes between Heptakis (2, 3, 6-tri-O-methyl)-beta-cyclodextrin and Various Alkanes or Alkenes (5? C? 10)?
Cardinael P, et al.
Journal of Inclusion Phenomena and Macrocyclic Chemistry, 39(1-2), 159-167 (2001)
Frantzeska Tsorteki et al.
Carbohydrate research, 339(2), 233-240 (2003-12-31)
The crystal structures of the complexes of heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin with indole-3-butyric acid and with 2,4-dichlorophenoxyacetic acid were studied by X-ray diffraction. The complexes crystallize in the monoclinic P2(1) space group. The host molecules are elliptically puckered and stacked along the a
Juziro Nishijo et al.
Chemical & pharmaceutical bulletin, 52(12), 1405-1410 (2004-12-04)
The interaction of cholesterol with heptakis (2,3,6-tri-O-methyl)-beta-cyclodextrin (TOM-beta-CyD) was investigated in water using solubility method. It was found that TOM-beta-CyD forms two kinds of soluble complexes, with molar ratios of 1:1 and 1:2 (cholesterol:TOM-beta-CyD). The thermodynamic parameters for 1:1 and
Xiaoxia Ge et al.
Se pu = Chinese journal of chromatography, 23(3), 305-307 (2005-08-30)
Heptakis (2,3,6-tri-O-ethyl)-beta-cyclodextrin (CD) (perethylated-beta-CD), heptakis (2,3,6-tri-O-propyl)-beta-CD (perpropylated-beta-CD), heptakis (2,3,6-tri-O-octyl)-beta-CD (peroctylated-beta-CD), and (2,6-di-O-benzyl)-beta-CD were used as stationary phases to prepare columns for gas chromatography by sol-gel technique. The method of coating the columns is similar to the dynamic method and the
Mingming Yin et al.
Se pu = Chinese journal of chromatography, 29(1), 91-94 (2011-05-18)
A new chiral stationary phase for gas chromatography, heptakis (2, 3, 6-tri-O-methoxymethyl)-beta-cyclodextrin, was synthesized by substituting the 2,3,6-OH groups of beta-cyclodextrin with methoxymethyl groups, and a coated capillary column for gas chromatography was made by coating this new stationary phase
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