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Sigma-Aldrich

Carboxymethyl-β-cyclodextrin sodium salt

Synonym(s):

Sodium CM-β-Cyclodextrin

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About This Item

CAS Number:
2828447-14-7
MDL number:
MFCD00285608
UNSPSC Code:
12352201
PubChem Substance ID:
57647952
NACRES:
NA.25

form

solid

Quality Level

100

impurities

10% water

mp

~245 °C (dec.)

solubility

H2O: 50 mg/mL, clear to slightly hazy, colorless

SMILES string

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

InChI

1S/C56H84O49/c57-22(58)8-85-1-15-43-29(71)36(78)50(92-15)100-44-16(2-86-9-23(59)60)94-52(38(80)31(44)73)102-46-18(4-88-11-25(63)64)96-54(40(82)33(46)75)104-48-20(6-90-13-27(67)68)98-56(42(84)35(48)77)105-49-21(7-91-14-28(69)70)97-55(41(83)34(49)76)103-47-19(5-89-12-26(65)66)95-53(39(81)32(47)74)101-45-17(3-87-10-24(61)62)93-51(99-43)37(79)30(45)72/h15-21,29-56,71-84H,1-14H2,(H,57,58)(H,59,60)(H,61,62)(H,63,64)(H,65,66)(H,67,68)(H,69,70)/t15-,16-,17-,18-,19-,20-,21-,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

WROHVVIPQXODQM-LYSKQWNXSA-N

Related Categories

General description

Carboxymethyl-β-cyclodextrin, a negatively charged derivative of β-cyclodextrin, is generally used in the chiral analysis of neutral and basic analytes on account of its ability to exhibit counter-current mobility.

Application

Cyclodextrins (CD) are cyclic oligosaccharides composed of D-glucose units connected via α(1→4) glycosidic bonds. Common cyclodextrins contain six (α-CD); seven (β-CD) or eight (gamma-CD) D-glucose units. Cyclodextrins are sometimes derivitized through esterification at positions two, three and/or six.
Carboxymethyl-β-cyclodextrin (CMBCD) is used in the development of recognition and separation technologies to resolve enantiomers based on chiral properties and size. Carboxymethyl-β-cyclodextrin is used in chiral selection and separation by capillary electrophoresis. Carboxymethyl-β-cyclodextrin is used in the development of drug delivery vehicles such as nanocarriers and as a nucleic acid transfection agent.

Analysis Note

average degree of substitution, DS ~3

Other Notes

To gain a comprehensive understanding of our extensive range of Polysaccharides for your research, we encourage you to visit our Carbohydrates Category page.

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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Chiral Separations: Methods and Protocols
Methods in Molecular Biology (2004)
Li-Li Ren et al.
Journal of nanoscience and nanotechnology, 10(11), 7262-7265 (2010-12-09)
Mammalian cochlear hair cells don't regenerate naturally after injury, which usually leave permanent hearing loss. Math1 gene is a positive regulator of hair cell differentiation during cochlear development and was proved to be very critical in hair cell regeneration in
Selective recognition and separation of nucleosides using carboxymethyl-β-cyclodextrin functionalized hybrid magnetic nanoparticles.
Badruddoza AZ, Junwen L, et al.
Colloids and Surfaces, B: Biointerfaces, 92, 223-231 (2012)
Felipe A Oyarzun-Ampuero et al.
Macromolecular bioscience, 12(2), 176-183 (2011-11-24)
A new nanomedicine consisting of chitosan/carboxymethyl-β-cyclodextrin loaded with unfractioned or low-molecular-weight heparin is described and its potential in asthma treatment is evaluated. The nanoparticles are prepared by ionotropic gelation showing a size that between 221 and 729 nm with a
Thitirat Mantim et al.
Electrophoresis, 33(2), 388-394 (2011-12-16)
CE methods with capacitively coupled contactless conductivity detection (C(4)D) were developed for the enantiomeric separation of the following stimulants: amphetamine (AP), methamphetamine (MA), ephedrine (EP), pseudoephedrine (PE), norephedrine (NE) and norpseudoephedrine (NPE). Acetic acid (pH 2.5 and 2.8) was found

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