(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(undecyloxy)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 155886
• Molecular Formular: C23H44O11
• Molecular Mass: 496.58886
• Monoisotopic Mass: 496.28836223
• SMILES: CCCCCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O
• Canonical SMILES: CCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C23H44O11/c1-2-3-4-5-6-7-8-9-10-11-31-22-20(30)18(28)21(15(13-25)33-22)34-23-19(29)17(27)16(26)14(12-24)32-23/h14-30H,2-13H2,1H3/t14-,15-,16-,17+,18-,19-,20-,21-,22-,23-/m1/s1
• InChIKey: UYEMNFYVTFDKRG-ZNGNCRBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(undecyloxy)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(undecyloxy)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Undecyl β-D-maltopyranoside; Undecyl β-D-maltoside; Detergent Screening Solution 25/Fluka kit no 66317; Undecyl β-D-maltopyranoside solution; Undecyl β-D-maltoside solution

Database IDs

• CAS Number: 253678-67-0
• MDL Number: MFCD01863130
• Beilstein Number: 9372606
• PubChem SID: 162250024; 24845777; 24889951
• PubChem CID: 447793

CALCULATED PROPERTIES

• Acid pKa: 11.939976
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): 0.37563115
• LogD (pH = 7.4): 0.3756188
• Log P: 0.3756313
• Molar Refractivity: 119.1685 cm^3
• Polarizability: 48.96104 Å^3
• Polar Surface Area: 178.53 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +49±1°, c = 2% in H2O
• Critical Micelle Concentration: 0.59 mM(20-25°C)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥99.0% (TLC)
• Concentration: 10 mM
• Description: non-ionic
• Empirical Formula (Hill Notation): C23H44O11

DETAILS

Sigma Aldrich - 94206

Application
Detergent for the purification, extraction and solubilization of membrane-bound proteins in the native structure. It increases solubilization by dissociating aggregates and is easily removed by dialysis.1