Wedelolactone

Base Information

• Chemical Name: Wedelolactone
• CAS No.: 524-12-9
• Molecular Formula: C16H10O7
• Molecular Weight: 314.251
• Hs Code.: 29322090
• European Community (EC) Number: 637-054-5
• UNII: 0K6L725GNS
• ChEMBL ID: CHEMBL97453
• DSSTox Substance ID: DTXSID60200408
• Metabolomics Workbench ID: 23001
• Nikkaji Number: J11.582G
• Pharos Ligand ID: PKTGK19D9B4G
• Wikidata: Q6586709
• Wikipedia: Wedelolactone
• Mol file: 524-12-9.mol

Synonyms:wedelolactone

Chemical Property of Wedelolactone

Chemical Property:

• Appearance/Colour: brown-beige solid
• Vapor Pressure: 1.48E-10mmHg at 25°C
• Melting Point: 327～330℃
• Refractive Index: 1.758
• Boiling Point: 498.4 °C at 760 mmHg
• PKA: 6.90±0.20(Predicted)
• Flash Point: 255.2 °C
• PSA: 113.27000
• Density: 1.655 g/cm³
• LogP: 2.81780
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 14 mg/mL, soluble
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 314.04265265
• Heavy Atom Count: 23
• Complexity: 483

Purity/Quality:

98%,99%, ^*data from raw suppliers

Wedelolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=C2C(=C1)OC(=O)C3=C2OC4=CC(=C(C=C43)O)O)O
• Uses: Wedelolactone is inhibits caspase-11; a key regulator of proinflammatory cytokine IL-1β maturation and apoptosis.

Technology Process of Wedelolactone

There total 28 articles about Wedelolactone 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: 93.0%

2-(2,6-dihydroxy-4-methoxy-phenyl)-5,6-dihydroxy-benzofuran-3-carboxylic acid methyl ester (627489-05-8) → wedelolactone (524-12-9)

Guidance literature:

With sulfuric acid; acetic acid; In water; at 50 ℃; for 1h;

DOI:10.1021/jo030228f

Reference yield: 87.0%

1-hydroxy-3-methoxy-8,9-diisopropyloxy-benzo[4,5]furo[3,2-c]chromen-6-one (1023744-97-9) → wedelolactone (524-12-9)

Guidance literature:

With boron trichloride; In dichloromethane; at 0 ℃;

DOI:10.1016/j.tet.2008.02.031

Reference yield: 82.0%

1,8,9-tris(benzyloxy)-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (115623-32-0) → wedelolactone (524-12-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In 1,4-dioxane; Product distribution; 2nd step of purification of 9 (wedelolactone);

upstream raw materials:

4,5-dihydroxy-7-methoxy coumarin

benzene-1,2-diol

1,8,9-tris(benzyloxy)-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one

2-(2,6-dihydroxy-4-methoxy-phenyl)-5,6-dihydroxy-benzofuran-3-carboxylic acid methyl ester

Downstream raw materials:

1,8,9-tris(benzyloxy)-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one

Refernces

• 1、 Chang, Chia-Fu,Yang, Ling-Yi,Chang, Shiao-Wei,Fang, Yu-Ting,Lee, Yean-Jang. "Total synthesis of demethylwedelolactone and wedelolactone by Cu-mediated/Pd(0)-catalysis and oxidative-cyclization". . p. 3661 - 3666. Retrieved 2008/09/20.
• 2、 Li, Chuang Chuang,Xie, Zhi Xiang,Zhang, Yan Dong,Chen, Jia Hua,Yang, Zhen. "Total Synthesis of Wedelolactone". . p. 8500 - 8504. Retrieved 2007/10/03.