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

• ChemBase ID: 155498
• Molecular Formular: C12H15NO8
• Molecular Mass: 301.2494
• Monoisotopic Mass: 301.07976645
• SMILES: c1cc(ccc1[N+](=O)[O-])O[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2)[N+](=O)[O-])[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-3-1-6(2-4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9-,10+,11+,12-/m1/s1
• InChIKey: IFBHRQDFSNCLOZ-LDMBFOFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol
• Synonyms: p-Nitrophenyl β-D-mannopyranoside; 4-Nitrophenyl β-D-mannopyranoside; Man1-β-PNP; 4-Nitrophenyl β-D-Mannopyranoside; p-Nitrophenyl β-D-Mannopyranoside

Database IDs

• CAS Number: 35599-02-1
• EC Number: 252-633-9
• MDL Number: MFCD00067650
• Beilstein Number: 1436646
• PubChem SID: 162249636; 24897475
• PubChem CID: 161880

CALCULATED PROPERTIES

• Acid pKa: 12.200142
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.6584035
• LogD (pH = 7.4): -0.6584103
• Log P: -0.6584034
• Molar Refractivity: 67.508 cm^3
• Polarizability: 26.651247 Å^3
• Polar Surface Area: 145.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble10 mg/mL, clear, very faintly yellow; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 185-189°C; 207-209 °C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98%; ≥99.0% (TLC)
• Impurities: ≤0.01% free 4-nitrophenol
• Empirical Formula (Hill Notation): C12H15NO8

DETAILS

Sigma Aldrich - 73727

Other Notes
β-D-Mannosidase activity1

REFERENCES

• Yang, L., et al.: J. Agric. Food Chem., 52, 1940 (2004)
• Hrmova, M., et al.: Biochem. J., 399, 77 (2004)
• Namdjou, D., et al.: ChemBioChem., 9, 1632 (2004)