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

• ChemBase ID: 103627
• Molecular Formular: C18H36O6
• Molecular Mass: 348.47484
• Monoisotopic Mass: 348.25118887
• SMILES: O(CCCCCCCCCCCC)[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO
• Canonical SMILES: CCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C18H36O6/c1-2-3-4-5-6-7-8-9-10-11-12-23-18-17(22)16(21)15(20)14(13-19)24-18/h14-22H,2-13H2,1H3/t14-,15-,16+,17-,18-/m1/s1
• InChIKey: PYIDGJJWBIBVIA-UYTYNIKBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-(dodecyloxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: lauryl glucoside
• Synonyms: n-Dodecyl β-D-glucopyranoside; n-Dodecyl glucoside; n-DODECYL-β-D-GLUCOPYRANOSIDE; Dodecyl glucoside; Lauryl glucoside

Database IDs

• CAS Number: 59122-55-3
• EC Number: 261-614-4
• MDL Number: MFCD00063298
• Beilstein Number: 86236
• PubChem SID: 24894182; 162091336
• PubChem CID: 93321
• Wikipedia Title: Lauryl_glucoside

CALCULATED PROPERTIES

• Acid pKa: 12.210987
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 2.5910356
• LogD (pH = 7.4): 2.591029
• Log P: 2.5910356
• Molar Refractivity: 91.3562 cm^3
• Polarizability: 37.058647 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -24±2°, c = 1% in methanol
• Critical Micelle Concentration: 0.13

Safety Information

• Storage Condition: 0°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R36/37/38
• Safety Statements: 26-36; S26 S36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (GC); ≥99.0% (TLC)
• Description: non-ionic
• Empirical Formula (Hill Notation): C18H36O6

DETAILS

Sigma Aldrich - D8035

Application
Dodecyl β-D-glucopyranoside, a long chain alkyl glycopyranoside and a classical nonionic amphiphile surfactant, is used in colloid research and micelle development.

Sigma Aldrich - 44203

Other Notes
Nonionic detergent useful in the solubilization of membrane-bound protein1