Diacerein

Base Information

• Chemical Name: Diacerein
• CAS No.: 13739-02-1
• Molecular Formula: C19H12O8
• Molecular Weight: 368.299
• Hs Code.: 29146990
• European Community (EC) Number: 237-310-2,839-256-0
• NSC Number: 758147
• UNII: 4HU6J11EL5
• DSSTox Substance ID: DTXSID4045636
• Nikkaji Number: J14.479G
• Wikipedia: Diacerein
• Wikidata: Q413178
• NCI Thesaurus Code: C166759
• Pharos Ligand ID: MMWKN7ZDZZ3C
• Metabolomics Workbench ID: 71535
• ChEMBL ID: CHEMBL41286
• Mol file: 13739-02-1.mol

Synonyms:1,8-diacetoxy-3-carboxyanthraquinone;2-anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-;4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid;4,5-diacetoxyanthraquinone-2-carboxylic acid;9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid, diacetate;AC-201;AC-203;Artrodar;diacerein;diacerhein;diacetyl-rhein;diacetylrhein;Diora;Fisiodar;M-01AX21;M01AX21;rhein diacetate;SF-277;SF277;Verboril;Zondar

Chemical Property of Diacerein

Chemical Property:

• Appearance/Colour: yellow crystalline solid
• Vapor Pressure: 8.17E-17mmHg at 25°C
• Melting Point: 217-218 °C
• Refractive Index: 1.634
• Boiling Point: 631.5 °C at 760 mmHg
• PKA: 3.01±0.20(Predicted)
• Flash Point: 231.8 °C
• PSA: 124.04000
• Density: 1.491 g/cm³
• LogP: 2.01080
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Sparingly), Methanol (Slightly)
• Water Solubility.: 240μg/L at 25℃
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 368.05321734
• Heavy Atom Count: 27
• Complexity: 683

Purity/Quality:

99%, ^*data from raw suppliers

Diacerein ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1=CC=CC2=C1C(=O)C3=C(C2=O)C=C(C=C3OC(=O)C)C(=O)O
• Recent ClinicalTrials: Evaluation of the Structural Modification Effect of Diacerein (Artrodar?) in Knee Osteoarthritic Patients
• Recent EU Clinical Trials: A Multi-center Study to Evaluate the Pharmacokinetics of Diacerein and Rhein and the Safety of Diacerein after Maximum Use, Topical Administration of CCP-020 (Diacerein 1% ointment) to Patients with Epidermolysis Bullosa (EB)
• Uses: It is widely used in new liquid crystal polymer, engineering plastics and high-strength fibers with high performance. This product is an important osteoarthritis IL-1 inhibitor. It is used for osteoarthritis. It is a natural antioxidant, it has anti-aging, enhance immunity, removing sub-health state, physical recovery, increasing energy and body immunity effects. A diacetyl derivative of Rhein. Demonstrates anti-arthritic activity without inhibiting prostaglandin synthesis. Antiarthritic antiinflammatory A diacetyl derivative of Rhein (R318500). Demonstrates anti-arthritic activity without inhibiting prostaglandin synthesis. Antiarthritic. Treatment of Osteoarthritis (Prevent cartilage destruction) Diacerein is a diacetyl precursor of rhein, an anthraquinone found in plants. Rhein, at 10 μM, inhibits IL-1β signaling, suppressing signaling through NF-κB and AP-1, and reduces the expression of the matrix metalloproteases MMP-1 and MMP-13. Diacerein, presumably after conversion to rhein, down-regulates the expression of the IL-1β receptor on articular chondrocytes, enhances the expression of TGF-β, and increases collagen and aggrecan. It does not alter COX activity. It is mildly effective in ameliorating osteoarthritis.
• Description: Diacerein is a disease-modifying antirheumatic drug (DMARD), reported to be useful in the treatment of various inflammatory conditions, including osteoarthritis. It forms water soluble chelates with calcium and copper, acting ultimately to reduce the activity of lysosomal enzymes and decrease the formation of rheumatoid factor.

Technology Process of Diacerein

There total 22 articles about Diacerein 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: 100.0%

1,8-dihydroxy-3-carboxy-anthraquinone (478-43-3) + acetic anhydride (108-24-7) → diacetylrhein (13739-02-1)

Guidance literature:

With pyridine; dmap;

DOI:10.1016/j.tetlet.2007.07.218

Reference yield: 84.0%

1,8-diacetoxy-3-methyl-anthraquinone (18713-45-6) → diacetylrhein (13739-02-1)

Guidance literature:

With chromium(VI) oxide; acetic anhydride; acetic acid; at 70 ℃;

DOI:10.1039/d1ob02202d

Reference yield: 54.6%

1,8-diacetoxy-3-carboxaldehyde-9,10-anthraquinone → diacetylrhein (13739-02-1)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate dihydrate; water; In dimethyl sulfoxide; acetone; for 9h;

upstream raw materials:

1,8-dihydroxy-3-carboxy-anthraquinone

acetic anhydride

1,8-diacetoxy-3-methyl-anthraquinone

acetic acid

Refernces

• 1、 Nawa,Uchibayashi,Matsuoka. "". . p. 979. Retrieved 1961.
• 2、 Li, Su-Yi,Jiang, Neng,Xie, Sai-Sai,Wang, Kelvin D. G.,Wang, Xiao-Bing,Kong, Ling-Yi. "Design, synthesis and evaluation of novel tacrine-rhein hybrids as multifunctional agents for the treatment of Alzheimer's disease". . p. 801 - 814. Retrieved 2014.
• 3、 Oesterle. "-". . p. 604. Retrieved 1903.
• 4、 -. "Diacerein synthesis method based on anthraquinone medicines". Paragraph 0023; 0024; 0029. . Retrieved 2020/07/27.
• 5、 -. "A kind of rhubarb acid thioamide compound, its preparation and use (by machine translation)". Paragraph 0041. . Retrieved 2017/11/16.