4-Nitrophenylrhamnoside

Base Information

• Chemical Name: 4-Nitrophenylrhamnoside
• CAS No.: 18918-31-5
• Molecular Formula: C₁₂H₁₅NO₇
• Molecular Weight: 285.254
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID20172314
• Nikkaji Number: J793.982E
• Wikidata: Q72495796
• Mol file: 18918-31-5.mol

Synonyms:4-nitrophenylrhamnoside;para-nitrophenyl-alpha-L-rhamnoside

Chemical Property of 4-Nitrophenylrhamnoside

Chemical Property:

• Melting Point: 179°C
• Boiling Point: 515.4±50.0 °C(Predicted)
• PKA: 12.68±0.70(Predicted)
• PSA: 124.97000
• Density: 1.503±0.06 g/cm3(Predicted)
• LogP: 0.32430
• Storage Temp.: −20°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 285.08485182
• Heavy Atom Count: 20
• Complexity: 339

Purity/Quality:

98%, ^*data from raw suppliers

4-Nitrophenyl a-L-rhamnopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2=CC=C(C=C2)[N+](=O)[O-])O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)[N+](=O)[O-])O)O)O
• Uses: 4-Nitrophenyl α-L-Rhamnopyranoside is a chromogenic substrate for naringinase. 4-Nitrophenyl α-L-rhamnopyranoside has been used as a substrate to determine β-glucosidase activity. It has also been used as a substrate to measure α-L-rhamnosidase activity of Oenococcus oeni and Aspergillus terreus.

Technology Process of 4-Nitrophenylrhamnoside

There total 4 articles about 4-Nitrophenylrhamnoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.6%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 2,3,4‐tri‐O‐acetyl-α-L‐rhamnopyranosyl chloride (5160-09-8) → p-nitrophenyl α-L-rhamnopyranoside (1226-39-7,10231-84-2,18918-31-5,22153-71-5,33095-26-0,73351-15-2,74032-91-0,140387-70-8)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; at 30 ℃; for 4.5h; Reagent/catalyst;

DOI:10.1080/07328303.2017.1390578

Reference yield:

4-nitrophenyl-2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranoside (18992-37-5) → p-nitrophenyl α-L-rhamnopyranoside (1226-39-7,10231-84-2,18918-31-5,22153-71-5,33095-26-0,73351-15-2,74032-91-0,140387-70-8)

Guidance literature:

With methanol; sodium methylate;

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → p-nitrophenyl α-L-rhamnopyranoside (1226-39-7,10231-84-2,18918-31-5,22153-71-5,33095-26-0,73351-15-2,74032-91-0,140387-70-8)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc chloride / 120 °C / unter vermindertem Druck

2: sodium methylate; methanol

With methanol; sodium methylate; zinc(II) chloride;

upstream raw materials:

4-nitrophenyl-2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranoside

4-nitro-phenol

2,3,4‐tri‐O‐acetyl-α-L‐rhamnopyranosyl chloride

Downstream raw materials:

p-nitrophenyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

p-trifluoroacetamidophenyl 4-O-α-D-glucopyranosyl-α-L-rhamnopyranoside

p-nitrophenyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-L-rhamnopyranoside

p-trifluoroacetamidophenyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-L-rhamnopyranoside

Refernces