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

• ChemBase ID: 153187
• Molecular Formular: C22H42O10S
• Molecular Mass: 498.62788
• Monoisotopic Mass: 498.24986854
• SMILES: CCCCCCCCCCS[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: CCCCCCCCCCS[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/C22H42O10S/c1-2-3-4-5-6-7-8-9-10-33-22-19(29)17(27)20(14(12-24)31-22)32-21-18(28)16(26)15(25)13(11-23)30-21/h13-29H,2-12H2,1H3/t13-,14-,15-,16+,17-,18-,19-,20-,21-,22+/m1/s1
• InChIKey: YZNNXXWNKQOETJ-HYLFJBCQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-(decylsulfanyl)-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,6S)-6-(decylsulfanyl)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Decyl-β-D-1-thiomaltopyranoside; Decyl-β-D-1-thiomaltopyranoside solution

Database IDs

• CAS Number: 148565-56-4
• EC Number: 231-791-2
• MDL Number: MFCD01862991
• PubChem SID: 24864014; 162247326; 24858578
• PubChem CID: 10345813

CALCULATED PROPERTIES

• Acid pKa: 12.063977
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): 0.5382758
• LogD (pH = 7.4): 0.5382665
• Log P: 0.5382759
• Molar Refractivity: 120.7369 cm^3
• Polarizability: 49.466656 Å^3
• Polar Surface Area: 169.3 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +53.0±3°, c = 0.5% in methanol
• Critical Micelle Concentration: 0.9 mM(20-25°C)

Safety Information

• German water hazard class: 2; 3
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (TLC)
• Concentration: 10 mM
• Description: non-ionic
• Empirical Formula (Hill Notation): C22H42O10S

DETAILS

Sigma Aldrich - 30727

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