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

• ChemBase ID: 155909
• Molecular Formular: C21H40O10S
• Molecular Mass: 484.6013
• Monoisotopic Mass: 484.23421848
• SMILES: CCCCCCCCCS[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: CCCCCCCCCS[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/C21H40O10S/c1-2-3-4-5-6-7-8-9-32-21-18(28)16(26)19(13(11-23)30-21)31-20-17(27)15(25)14(24)12(10-22)29-20/h12-28H,2-11H2,1H3/t12-,13-,14-,15+,16-,17-,18-,19-,20-,21+/m1/s1
• InChIKey: AFOMEWLJBOWKCP-OHQXVXRSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(nonylsulfanyl)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)-4,5-dihydroxy-2-(hydroxymethyl)-6-(nonylsulfanyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Nonyl-β-D-1-thiomaltoside

Database IDs

• CAS Number: 148565-55-3
• MDL Number: MFCD00674538
• PubChem SID: 24886480; 162250047
• PubChem CID: 11663071

CALCULATED PROPERTIES

• Acid pKa: 12.063977
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): 0.09370711
• LogD (pH = 7.4): 0.09369782
• Log P: 0.093707226
• Molar Refractivity: 116.1359 cm^3
• Polarizability: 47.64231 Å^3
• Polar Surface Area: 169.3 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +36±1°, c = 0.1% in methanol
• Critical Micelle Concentration: 3.2

Safety Information

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

Product Information

• Purity: ≥98.0% (TLC)
• Description: non-ionic
• Empirical Formula (Hill Notation): C21H40O10S

DETAILS

Sigma Aldrich - 74436

General description
n-Nonyl-β-D-thiomaltoside is a newly developed detergent whose lipophilic moiety is maltose. This reagent is suitable for isolating proteins inside of cell membranes. The activity of protein isolated using n-Nonyl-β-D-thiomaltoside is higher than those isolated using n-Octyl-β-D-thioglucoside or n-Heptyl-β-D-thioglucoside. As the CMC value of this detergent is 2.4 mM, it is easy to remove from protein solutions by dialysis.