(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(octylsulfanyl)oxane-3,4,5-triol

• ChemBase ID: 6168
• Molecular Formular: C14H28O5S
• Molecular Mass: 308.43412
• Monoisotopic Mass: 308.165745
• SMILES: [C@@H]1([C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)SCCCCCCCC
• Canonical SMILES: CCCCCCCCS[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C14H28O5S/c1-2-3-4-5-6-7-8-20-14-13(18)12(17)11(16)10(9-15)19-14/h10-18H,2-9H2,1H3/t10-,11-,12+,13-,14+/m1/s1
• InChIKey: CGVLVOOFCGWBCS-RGDJUOJXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(octylsulfanyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(octylsulfanyl)oxane-3,4,5-triol
• Synonyms: 2-HYDROXYMETHYL-6-OCTYLSULFANYL-TETRAHYDRO-PYRAN-3,4,5-TRIOL; Octyl-thioglucoside; OCTYL-β-D-THIOGLUCOPYRANOSIDE; Octyl thioglucoside; Octyl β-D-1-thioglucopyranoside

Database IDs

• CAS Number: 85618-21-9
• MDL Number: MFCD00012189
• Beilstein Number: 4182783
• PubChem SID: 160969593; 24898030; 99445029
• PubChem CID: 656909

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.4819765
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.4199742
• LogD (pH = 7.4): 1.4199706
• Log P: 1.4199742
• Molar Refractivity: 79.1216 cm^3
• Polarizability: 32.079426 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.85
• LOG S: -1.92
• Solubility (Water): 3.67e+00 g/l

PROPERTIES

Physical Property

• Solubility: ethanol: soluble50 mg/mL, clear, colorless
• Apperance: crystalline
• Melting Point: 125-131 °C
• Optical Rotation: [α]/D -52 to -48°, c = 1 in ethanol; [α]20/D -50±2°, c = 1% in ethanol
• Critical Micelle Concentration: 9 mM(20-25°C)

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (GC); ≥99% (TLC); ≥99.0% (TLC)
• Description: non-ionic
• Impurities: ≤4% water; ≤5.5% water
• Cation Traces: Al: ≤5 mg/kg; Ba: ≤5 mg/kg; Bi: ≤10 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: sulfate (SO42-): ≤300 mg/kg
• Empirical Formula (Hill Notation): C14H28O5S

DETAILS

MP Biomedicals - 02152486

Crystalline A non-ionic detergent for solubilization of membrane proteins.

DrugBank - DB08558

Drug information: experimental

Sigma Aldrich - O6004

Application
A non-ionic detergent for solubilization and reconstitution of membrane proteins.

Sigma Aldrich - 75082

Other Notes
A new, non-ionic, non-denaturing detergent for the solubilization and reconstitution of membrane proteins; much more stable than the frequently used octyl-β-glucopyranoside1,2

REFERENCES

• Saito, S. and Tsuchiya, T., Biochem. J., 222: 829 (1984).