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

• ChemBase ID: 132952
• Molecular Formular: C12H15NO8
• Molecular Mass: 301.2494
• Monoisotopic Mass: 301.07976645
• SMILES: c1ccc(c(c1)[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](Oc2ccccc2[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)20-7-4-2-1-3-6(7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9-,10+,11-,12-/m1/s1
• InChIKey: KUWPCJHYPSUOFW-RMPHRYRLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-nitrophenoxy)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-nitrophenoxy)oxane-3,4,5-triol
• Synonyms: 2-Nitrophenyl β-D-glucopyranoside

Database IDs

• CAS Number: 2816-24-2
• EC Number: 220-568-5
• MDL Number: MFCD00065048
• Beilstein Number: 92206
• PubChem SID: 24897848; 162227229
• PubChem CID: 92941

CALCULATED PROPERTIES

• Acid pKa: 12.200035
• 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: 26.654507 Å^3
• Polar Surface Area: 145.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: powder
• Optical Rotation: [α]20/D -105±2°, c = 2% in H2O

Safety Information

• 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: ≥99.0% (HPLC)
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C12H15NO8
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 73674

Other Notes
Substrate for the detection of β-glucosidase1