Probucol

Base Information

• Chemical Name: Probucol
• CAS No.: 23288-49-5
• Molecular Formula: C31H48O2S2
• Molecular Weight: 516.853
• Hs Code.: 2930902000
• European Community (EC) Number: 245-560-9
• NSC Number: 757837,652160,86225
• UNII: P3CTH044XJ
• DSSTox Substance ID: DTXSID2045440
• Nikkaji Number: J20.410B
• Wikipedia: Probucol
• Wikidata: Q10354103
• NCI Thesaurus Code: C66470
• Pharos Ligand ID: 5GBBQAPNX6AV
• Metabolomics Workbench ID: 43586
• ChEMBL ID: CHEMBL608
• Mol file: 23288-49-5.mol

Synonyms:Biphenabid;DH 581;DH-581;DH581;Lorelco;Lurselle;Panavir;Probucol;Superlipid

Chemical Property of Probucol

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 1.46E-12mmHg at 25°C
• Melting Point: 126-128 °C
• Refractive Index: 1.573
• Boiling Point: 546.7 °C at 760 mmHg
• PKA: 10.27±0.70(Predicted)
• Flash Point: 264.9 °C
• Density: 1.07 g/cm³
• Storage Temp.: Desiccate at +4°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 11.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 516.30957312
• Heavy Atom Count: 35
• Complexity: 583

Purity/Quality:

99.90% ^*data from raw suppliers

Probucol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)SC(C)(C)SC2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C
• Recent ClinicalTrials: The Effect of InTensive Statin in Ischemic Stroke With inTracranial Atherosclerotic Plaques
• Recent NIPH Clinical Trials: None
• Description: Probucol is a kind of bis-phenol antioxidant with anti-hyperlipidemic activity. It had been initially developed for the treatment of coronary artery disease. However, its clinical trials were stopped after people found that it could lower the HDL and LDL cholesterol in patients of a history of heart disease. Probucol exerts its effect through accelerating the fractional rate of low-density (LDL) catabolism which is in the final pathway of cholesterol elimination inside the body. It may also inhibit the early stage of cholesterol biosynthesis and dietary cholesterol absorption.
• Uses: antihyperlipidemic Probucol is an antilipemic. anti-hyperlipoproteinemic An antioxidant, anti-inflammatory, and hypocholesterolemic agent which inhibits atherogenesis in murine models.
• Biological Functions: Probucol (Lorelco) is a hypocholesterolemic drug with few side effects that modestly (15–30%) decreases elevated plasma LDL cholesterol levels. The marginal LDL-lowering action plus reports that it can lower HDL cholesterol resulted in its discontinuation as a hypocholesterolemic drug. However, it still may reduce the risk of CHD because it is a powerful antioxidant. The oxidation hypothesis of atherosclerosis states that oxidation of lipids in LDL is required for LDL uptake by macrophages and smooth muscle cells in the intima of arteries, leading to their transformation to foam cells, an early event in atherogenesis. A recent clinical trial reported that use of probucol decreased the rate of restenosis of coronary arteries by 50% in patients who underwent angioplasty. Fluvastatin also has potent antioxidant properties that may contribute to its antiatherosclerotic effects.These findings suggest that reducing high plasma lipids may not be the only approach to retarding the progression of atherosclerosis and decreasing the risk of coronary heart disease.

Technology Process of Probucol

There total 3 articles about Probucol 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: 82.0%

4-hydroxy-3,5-di-tert-butylthiophenol (950-59-4) + acetone (67-64-1) → (4,4'-isopropylidenedithio)bis[2,6-di-tert-butylphenol] (23288-49-5)

Guidance literature:

With hydrogenchloride; In methanol; water; at 50 - 55 ℃; for 5h;

Reference yield:

probucol radical → (4,4'-isopropylidenedithio)bis[2,6-di-tert-butylphenol] (23288-49-5)

Guidance literature:

With 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone; In toluene; at 24.9 ℃; Equilibrium constant;

DOI:10.1021/jo00096a061

Reference yield:

→ (4,4'-isopropylidenedithio)bis[2,6-di-tert-butylphenol] (23288-49-5)

Guidance literature:

upstream raw materials:

4-hydroxy-3,5-di-tert-butylthiophenol

acetone

Downstream raw materials:

probucol monosuccinate

phenol

2,2'-oxybis-acetic acid

1,5-pentanedioic acid

Refernces

• 1、 -. "Process for preparation of probucol derivatives". Page/Page column 3-4. . Retrieved 2008/06/13.
• 2、 -. "Carotenoid analogs or derivatives for controlling C-reactive protein levels". . . Retrieved 2008/06/13.