4-oxo-4-{[(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-pentakis({[(3-carboxypropanoyl)oxy]methyl})-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-35-{[(4-oxopentanoyl)oxy]methyl}-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}butanoic acid

• ChemBase ID: 155826
• Molecular Formular: C71H100O55
• Molecular Mass: 1833.5207
• Monoisotopic Mass: 1832.5028073
• SMILES: CC(=O)CCC(=O)OC[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)COC(=O)CCC(=O)O)COC(=O)CCC(=O)O)COC(=O)CCC(=O)O)COC(=O)CCC(=O)O)COC(=O)CCC(=O)O)COC(=O)CCC(=O)O)O)O
• Canonical SMILES: CC(=O)CCC(=O)OC[C@H]1O[C@@H]2O[C@@H]3[C@@H](COC(=O)CCC(=O)O)O[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3[C@@H](COC(=O)CCC(=O)O)O[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3[C@@H](COC(=O)CCC(=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)COC(=O)CCC(=O)O)[C@@H](O)[C@@H]4O)COC(=O)CCC(=O)O)[C@@H](O)[C@@H]3O)COC(=O)CCC(=O)O
• InChI: InChI=1S/C71H100O55/c1-23(72)2-9-37(85)106-16-24-58-44(92)51(99)65(113-24)121-59-25(17-107-38(86)10-3-31(73)74)115-67(53(101)46(59)94)123-61-27(19-109-40(88)12-5-33(77)78)117-69(55(103)48(61)96)125-63-29(21-111-42(90)14-7-35(81)82)119-71(57(105)50(63)98)126-64-30(22-112-43(91)15-8-36(83)84)118-70(56(104)49(64)97)124-62-28(20-110-41(89)13-6-34(79)80)116-68(54(102)47(62)95)122-60-26(18-108-39(87)11-4-32(75)76)114-66(120-58)52(100)45(60)93/h24-30,44-71,92-105H,2-22H2,1H3,(H,73,74)(H,75,76)(H,77,78)(H,79,80)(H,81,82)(H,83,84)/t24-,25-,26-,27-,28-,29-,30-,44+,45+,46+,47+,48+,49+,50+,51+,52+,53+,54+,55+,56+,57+,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-/m1/s1
• InChIKey: DIRLEDPEXJLCIL-JCWBWLHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-oxo-4-{[(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-pentakis({[(3-carboxypropanoyl)oxy]methyl})-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-35-{[(4-oxopentanoyl)oxy]methyl}-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}butanoic acid
• IUPAC Traditional name: 4-oxo-4-{[(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-pentakis({[(3-carboxypropanoyl)oxy]methyl})-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-35-{[(4-oxopentanoyl)oxy]methyl}-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}butanoic acid
• Synonyms: Succinyl-β-cyclodextrin

Database IDs

• MDL Number: MFCD00800297
• PubChem SID: 24888494; 162249964
• PubChem CID: 16218612

CALCULATED PROPERTIES

• Acid pKa: 2.805874
• H Acceptors: 48
• H Donor: 20
• LogD (pH = 5.5): -21.668894
• LogD (pH = 7.4): -30.2956
• Log P: -10.204307
• Molar Refractivity: 370.7578 cm^3
• Polarizability: 155.3033 Å^3
• Polar Surface Area: 837.41 Å^2
• Rotatable Bonds: 42
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Impurities: ~5% water

DETAILS

Sigma Aldrich - 85990

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.Succinyl-β-cyclodextrin and carboxymethyl-β-cyclodextrin are used as chiral selective agents in capillary electrophoresis for the separation of di- and tri-peptide enantiomers and catechin enantiomers. Succinyl-β-cyclodextrin is used to optimize analysis of PNA-DNA duplexes with diethylthiadicarbocyanine dye.