4-Nitrophenyl beta-D-glucopyranosiduronic acid

Base Information

• Chemical Name: 4-Nitrophenyl beta-D-glucopyranosiduronic acid
• CAS No.: 10344-94-2
• Molecular Formula: C12H13NO9
• Molecular Weight: 315.237
• Hs Code.: 29329990
• European Community (EC) Number: 233-753-0
• DSSTox Substance ID: DTXSID80209670
• Nikkaji Number: J236.780G
• Wikidata: Q27162353
• ChEMBL ID: CHEMBL495244
• Mol file: 10344-94-2.mol

Synonyms:4-nitrophenylglucuronide;p-nitrophenyl-beta-D-glucuronide;p-nitrophenylglucuronide;para-nitrophenylglucuronide

Chemical Property of 4-Nitrophenyl beta-D-glucopyranosiduronic acid

Chemical Property:

• Appearance/Colour: Crystalline solid
• Melting Point: 93 °C
• Boiling Point: 644.434 °C at 760 mmHg
• PKA: 2.69±0.70(Predicted)
• Flash Point: 343.541 °C
• PSA: 162.27000
• Density: 1.732 g/cm³
• LogP: -0.61100
• Storage Temp.: −20°C
• Solubility.: H2O: 0.1 g/mL, clear, faintly yellow
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 315.05903099
• Heavy Atom Count: 22
• Complexity: 417

Purity/Quality:

98.0%min ^*data from raw suppliers

p-Nitrophenyl b-D-Glucuronide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(C(O2)C(=O)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1[N+](=O)[O-])O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O
• Uses: 4-Nitrophenyl β-D-glucuronide has been used for determining the β-glucuronidase activity in urine samples, β-glucuronidase activity of bacteria in caecum content digesta and bovine liver. It has also been used to study the inhibitory effect of Phyllanthus amarus extracts on β-glucuronidase. 4-Nitrophenyl β-D-glucuronide has been used as substrate in acetate buffer to measure β-glucuronidase.

Technology Process of 4-Nitrophenyl beta-D-glucopyranosiduronic acid

There total 13 articles about 4-Nitrophenyl beta-D-glucopyranosiduronic acid 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: 85.0%

methyl <4'-nitrophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate (18472-49-6) → p-nitrophenyl-β-D-glucuronide (10344-94-2,60833-84-3)

Guidance literature:

With methanol; lithium hydroxide; at 20 ℃; for 4h; Inert atmosphere;

Reference yield: 63.0%

4-nitrophenyl-β-D-glucoside (2492-87-7) → p-nitrophenyl-β-D-glucuronide (10344-94-2,60833-84-3)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sodium hydrogencarbonate; potassium bromide; In water; acetone; at 0 - 45 ℃;

DOI:10.1246/bcsj.20100094

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + UDP-glucuronic acid (2616-64-0) → p-nitrophenyl-β-D-glucuronide (10344-94-2,60833-84-3)

Guidance literature:

With rat liver microsome solution; magnesium chloride; In various solvent(s); at 37 ℃; for 0.25h; pH=7.4;

DOI:10.1021/ac060970q

upstream raw materials:

4-nitro-phenol

UDP-glucuronic acid

Uridine diphospho-D-glucuronic acid triammonium salt

UDP-glucuronic acid

Downstream raw materials:

O¹-(4-amino-phenyl)-β-D-glucopyranuronic acid

phenyl 1-thio-β-D-glucopyranosiduronic acid

Refernces

• 1、 Kashima, Yousuke,Okabayashi, Yoshito. "Development of a rapid and detailed structural identification system with an on-line immobilized enzyme reactor integrated into LC-NMR". . p. 423 - 425. Retrieved 2010.
• 2、 Yamaguchi,Mori,Suketa. "Effects of Ca2+, Zn2+ and Cd2+ on uridine diphosphate-glucuronyltransferase and β-glucuronidase activities in rat liver microsomes". . p. 159 - 163. Retrieved 1990.
• 3、 -. "Preparation method of substituted benzyl or substituted phenyl beta-D-hexuronic acid glucoside". . . Retrieved 2018/10/19.