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

• ChemBase ID: 104430
• Molecular Formular: C12H15NO8
• Molecular Mass: 301.2494
• Monoisotopic Mass: 301.07976645
• SMILES: [O-][N+](=O)c1ccc(O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO)cc1
• 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-ZIQFBCGOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol
• Synonyms: p-NITROPHENYL-α-D-GLUCOPYRANOSIDE; 4-Nitrophenyl α-D-glucopyranoside; p-NITROPHENYL α-D-GLUCOPYRANOSIDE; p-Nitrophenyl α-D-glucopyranoside; 4-Nitrophenyl α-D-glucopyranoside; 4-Nitrophenyl α-D-Glucopyranoside; 4-Nitrophenyl α-D-Glucoside; p-Nitrophenol α-D-Glucoside; p-Nitrophenyl α-D-Glucopyranoside

Database IDs

• CAS Number: 3767-28-0
• EC Number: 223-189-3
• MDL Number: MFCD00064088
• Beilstein Number: 92212
• PubChem SID: 162091752; 24897484
• PubChem CID: 92969

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: Methanol; Warm Ethanol; Warm Water
• Apperance: White Crystals
• Melting Point: 209-213°C; 210-216 °C; 214-220°C
• Optical Rotation: [α]20/D +218±5°, c = 0.5% in H2O

Safety Information

• Storage Condition: 0°C; -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: ≥98.0% (HPLC); ≥99%
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C12H15NO8

DETAILS

MP Biomedicals - 05221149

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02155912

Crystalline

Sigma Aldrich - N1377

Frequently Asked Questions
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包装
1 g in poly tube
5, 25 g in poly bottle

Sigma Aldrich - 73673

Other Notes
Substrate for glucansucrases1; Substrate for yeast α-glucosidase2

Toronto Research Chemicals - N503650

Substrate for α-glucosidase inhibitor.

REFERENCES

• O'Neill, R., et al.: J. Biol. Chem., 264, 20430 (1989)
• Carpita, N., et al.: Plant J., 3, 1 (1989)
• Henrissat, B., et al.: Biochem. J., 293, 781 (1989)
• Nakai, H., et al.: Biochimie, 89, 49 (1989)