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

• ChemBase ID: 104009
• Molecular Formular: C14H28O6
• Molecular Mass: 292.36852
• Monoisotopic Mass: 292.18858862
• SMILES: O(CCCCCCCC)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO
• Canonical SMILES: CCCCCCCCO[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C14H28O6/c1-2-3-4-5-6-7-8-19-14-13(18)12(17)11(16)10(9-15)20-14/h10-18H,2-9H2,1H3/t10-,11-,12+,13-,14+/m1/s1
• InChIKey: HEGSGKPQLMEBJL-RGDJUOJXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(octyloxy)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(octyloxy)oxane-3,4,5-triol
• Synonyms: n-Octyl-alpha-D-Glucopyranoside; n-Octyl α-glucoside; n-OCTYL α-D-GLUCOPYRANOSIDE; n-Octyl α-glucoside; Octyl α-D-glucopyranoside

Database IDs

• CAS Number: 29781-80-4
• MDL Number: MFCD00070008
• Beilstein Number: 4232620
• PubChem SID: 162090750; 24897933
• PubChem CID: 445318

CALCULATED PROPERTIES

• Acid pKa: 12.210987
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.8127609
• LogD (pH = 7.4): 0.8127543
• Log P: 0.81276095
• Molar Refractivity: 72.9522 cm^3
• Polarizability: 29.735554 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 73.4 - 78.8°C
• Optical Rotation: [α]20/D +116±4°, c = 1% in methanol

Safety Information

• Storage Condition: 0°C, Desiccate
• 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% (GC); ≥98.0% (TLC); 98%
• Description: non-ionic
• Empirical Formula (Hill Notation): C14H28O6

DETAILS

MP Biomedicals - 02153942

Crystalline Purity: 98%

Sigma Aldrich - 75079

Other Notes
Typical amphiphile, suitable for the crystallization of membrane proteins1

REFERENCES

• Brown, G.M., et al., Canadian J. Chem., 48: 2525 (1970).