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

• ChemBase ID: 155982
• Molecular Formular: C28H54O11
• Molecular Mass: 566.72176
• Monoisotopic Mass: 566.36661255
• SMILES: CCCCCCCCCCCCCCCCO[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: CCCCCCCCCCCCCCCCO[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/C28H54O11/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-36-27-25(35)23(33)26(20(18-30)38-27)39-28-24(34)22(32)21(31)19(17-29)37-28/h19-35H,2-18H2,1H3/t19-,20-,21-,22+,23-,24-,25-,26-,27-,28-/m1/s1
• InChIKey: GTQCHJYVKDXMRU-YMEALESQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-6-(hexadecyloxy)-4,5-dihydroxy-2-(hydroxymethyl)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)-6-(hexadecyloxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Cetyl β-D-maltoside; Hexadecyl-β-D-maltoside; n-Hexadecyl β-D-maltoside; Detergent Screening Solution 27/Fluka kit no 66317; Hexadecyl-β-D-maltoside solution; Hexadecyl-β-D-maltosid 0.1 mM solution

Database IDs

• CAS Number: 98064-96-1
• EC Number: 231-791-2
• MDL Number: MFCD01310880
• PubChem SID: 24874303; 24846166; 162250120
• PubChem CID: 9850929

CALCULATED PROPERTIES

• Acid pKa: 11.939976
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): 2.5984745
• LogD (pH = 7.4): 2.598462
• Log P: 2.5984747
• Molar Refractivity: 142.1735 cm^3
• Polarizability: 58.092148 Å^3
• Polar Surface Area: 178.53 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +45±2°
• Critical Micelle Concentration: 0.0006 mM(20-25°C)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (TLC)
• Description: non-ionic
• Empirical Formula (Hill Notation): C28H54O11

DETAILS

Sigma Aldrich - 52318

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: N.C. Robinson et al., Biochemistry, 24, 6298 (1985)