2-{[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,37S,38S,39S,40S,41S,42S,43S,44S,45S,46S,47S,48S,49S)-10,15,20,25,30,35-hexakis[(carboxymethoxy)methyl]-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methoxy}acetic acid

• ChemBase ID: 156015
• Molecular Formular: C56H84O49
• Molecular Mass: 1541.23676
• Monoisotopic Mass: 1540.40811907
• SMILES: C([C@@H]1[C@@H]2[C@H]([C@@H]([C@H](O1)O[C@@H]1[C@H](O[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1[C@H](O[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1[C@H](O[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1[C@H](O[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1[C@H](O[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1[C@H](O[C@H](O2)[C@H]([C@@H]1O)O)COCC(=O)O)COCC(=O)O)COCC(=O)O)COCC(=O)O)COCC(=O)O)COCC(=O)O)O)O)OCC(=O)O
• Canonical SMILES: OC(=O)COC[C@H]1O[C@@H]2O[C@@H]3[C@@H](COCC(=O)O)O[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3[C@@H](COCC(=O)O)O[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3[C@@H](COCC(=O)O)O[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3[C@H](O[C@H](O[C@@H]4[C@H](O[C@H](O[C@@H]5[C@H](O[C@H](O[C@H]1[C@H]([C@@H]2O)O)[C@@H](O)[C@@H]5O)COCC(=O)O)[C@@H](O)[C@@H]4O)COCC(=O)O)[C@@H](O)[C@@H]3O)COCC(=O)O
• InChI: 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
• InChIKey: WROHVVIPQXODQM-LYSKQWNXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,37S,38S,39S,40S,41S,42S,43S,44S,45S,46S,47S,48S,49S)-10,15,20,25,30,35-hexakis[(carboxymethoxy)methyl]-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.2^3,^6.2^8,^1^1.2^1^3,^1^6.2^1^8,^2^1.2^2^3,^2^6.2^2^8,^3^1]nonatetracontan-5-yl]methoxy}acetic acid
• IUPAC Traditional name: {[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,37S,38S,39S,40S,41S,42S,43S,44S,45S,46S,47S,48S,49S)-10,15,20,25,30,35-hexakis[(carboxymethoxy)methyl]-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.2^3,^6.2^8,^1^1.2^1^3,^1^6.2^1^8,^2^1.2^2^3,^2^6.2^2^8,^3^1]nonatetracontan-5-yl]methoxy}acetic acid
• Synonyms: Carboxymethyl-β-cyclodextrin sodium salt

Database IDs

• MDL Number: MFCD00285608
• PubChem SID: 162250153; 24853105
• PubChem CID: 16211582

CALCULATED PROPERTIES

• Acid pKa: 2.3477378
• H Acceptors: 49
• H Donor: 21
• LogD (pH = 5.5): -27.536219
• LogD (pH = 7.4): -35.674946
• Log P: -11.54808
• Molar Refractivity: 302.7437 cm^3
• Polarizability: 127.57864 Å^3
• Polar Surface Area: 738.15 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless
• Melting Point: ~245 °C (dec.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Impurities: 10% water

DETAILS

Sigma Aldrich - 21906

Analysis Note
average degree of substitution, DS ~3
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.