5-Hydroxyrofecoxib

Base Information

• Chemical Name: 5-Hydroxyrofecoxib
• CAS No.: 185147-17-5
• Molecular Formula: C17H16O5S
• Molecular Weight: 330.361
• UNII: 8DJV9U9K61
• DSSTox Substance ID: DTXSID90433560
• Nikkaji Number: J1.426.755G
• Wikidata: Q27270230
• ChEMBL ID: CHEMBL1084
• Mol file: 185147-17-5.mol

Synonyms:5-hydroxyrofecoxib

Chemical Property of 5-Hydroxyrofecoxib

Chemical Property:

• Vapor Pressure: 3.44E-15mmHg at 25°C
• Melting Point: 95-104°C
• Boiling Point: 598.9°Cat760mmHg
• Flash Point: 316°C
• PSA: 89.05000
• Density: 1.365g/cm³
• LogP: 2.95690
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 330.05619472
• Heavy Atom Count: 23
• Complexity: 587

Purity/Quality:

99% ^*data from raw suppliers

5-HydroxyVioxx ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CS(=O)(=O)C1=CC=C(C=C1)C2=C(C(=O)OC2O)C3=CC=CC=C3
• Uses: As a metabolite of Vioxx, 5-Hydroxy Vioxx was highly dependent on the subcellular fraction and the redox system used. A metabolite of Vioxx. The biotransformation of Rofecoxib (Vioxx) was highly dependent on the subcellular fraction and the redox system used.

Technology Process of 5-Hydroxyrofecoxib

There total 7 articles about 5-Hydroxyrofecoxib 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: 92.0%

rofecoxib (162011-90-7) → 5-Hydroxyrofecoxib (185147-17-5)

Guidance literature:

With oxygen; pyrographite; In ethyl acetate;

DOI:10.1016/S0960-894X(00)00538-2

Reference yield:

aqueous NH4 OAc + Benzoic acid, 3-(4-(methylsulfonyl)phenyl)-5-oxo-4-phenyl-2,5-dihydrofuran-2-yl ester (185147-16-4) → 5-Hydroxyrofecoxib (185147-17-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol;

Reference yield:

rofecoxib (162011-90-7) → 5-Hydroxyrofecoxib (185147-17-5) + 4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one (179175-15-6)

Guidance literature:

With lithium hydroxide; air; In tetrahydrofuran; water; at 20 ℃; for 4h;

DOI:10.1016/j.tetlet.2004.12.055

upstream raw materials:

rofecoxib

(+/-)-5-bromo-4-[4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one

Benzoic acid, 3-(4-(methylsulfonyl)phenyl)-5-oxo-4-phenyl-2,5-dihydrofuran-2-yl ester

4-(Methylthio)acetophenone

Downstream raw materials:

5-Hydroxyrofecoxib glucuronide

2-cyclopropylmethyl-5-(4-methylsulfonyl)phenyl-4-phenyl-2H-pyridazin-3-one

5-(4-methylsulfonyl)phenyl-4-phenyl-2H-pyridazin-3-one

Refernces

• 1、 Reddy, Leleti Rajender,Corey. "Facile air oxidation of the conjugate base of rofecoxib (Vioxx), a possible contributor to chronic human toxicity". . p. 927 - 929. Retrieved 2007/10/03.
• 2、 Nicoll-Griffith, Deborah A.,Yergey, James A.,Trimble, Laird A.,Silva, Jose M.,Li, Chun,Chauret, Nathalie,Gauthier, Jacques Yves,Grimm, Erich,Leger, Serge,Roy, Patrick,Therien, Michel,Wang, Zhaoyin,Prasit, Peppi,Zamboni, Robert,Young, Robert N.,Brideau, Christine,Chan, Chi-Chung,Mancini, Joseph,Riendeau, Denis. "Synthesis, characterization, and activity of metabolites derived from the cyclooxygenase-2 inhibitor rofecoxib (MK-0966, Vioxx(TM))". . p. 2683 - 2686. Retrieved 2007/10/03.