Griseofulvin

Base Information

• Chemical Name: Griseofulvin
• CAS No.: 2884-22-2
• Deprecated CAS: 3426-54-8,8027-03-0,11103-62-1,24659-79-8,8055-10-5
• Molecular Formula: C₁₇H₁₇ClO₆
• Molecular Weight: 352.771
• European Community (EC) Number: 204-767-4
• NSC Number: 755822
• UNII: 32HRV3E3D5
• DSSTox Substance ID: DTXSID8020674
• Nikkaji Number: J4.418K
• Wikipedia: Griseofulvin
• Wikidata: Q416096
• NCI Thesaurus Code: C65819
• RXCUI: 5021
• Metabolomics Workbench ID: 27937
• ChEMBL ID: CHEMBL562
• Mol file: 2884-22-2.mol

Synonyms:Fulvicin U F;Fulvicin-U-F;FulvicinUF;Grifulvin V;Gris PEG;Gris-PEG;Grisactin;Grisefuline;Griseofulvin;GrisPEG

Chemical Property of Griseofulvin

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 352.0713660
• Heavy Atom Count: 24
• Complexity: 575

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Drug Classes: Antifungal Agents
• Canonical SMILES: CC1CC(=O)C=C(C12C(=O)C3=C(O2)C(=C(C=C3OC)OC)Cl)OC
• Isomeric SMILES: C[C@@H]1CC(=O)C=C([C@]12C(=O)C3=C(O2)C(=C(C=C3OC)OC)Cl)OC
• Recent ClinicalTrials: Bioequivalence (BE) Study of Test Griseofulvin 500 Milligram (mg) Tablets Versus Reference and Dose Proportionality Study of Test Griseofulvin 250 mg and 500 mg Tablets Under Fed Conditions

Technology Process of Griseofulvin

There total 24 articles about Griseofulvin 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: 46.0%

1,1-dimethoxy-3-trimethylsilyloxy-1,3-butadiene (61539-61-5) + (E)-7-chloro-2-ethylidene-4,6-dimethoxy-3(2H)-benzofuranone (129529-63-1) → griseofulvin (126-07-8,469-49-8,1588-01-8,2884-22-2,6915-11-3,67890-77-1,78739-00-1)

Guidance literature:

In toluene; for 2h; Heating;

DOI:10.1248/cpb.38.925

Reference yield: 44.0%

(+/-)-dehydrogriseofulvin (7776-77-4) → griseofulvin (126-07-8,469-49-8,1588-01-8,2884-22-2,6915-11-3,67890-77-1,78739-00-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 3h;

DOI:10.1248/cpb.38.925

Reference yield:

(-)-dehydrogriseofulvin (3573-90-8) → (-)-griseofulvin (126-07-8,469-49-8,1588-01-8,2884-22-2,6915-11-3,67890-77-1,78739-00-1) + griseofulvin (126-07-8)

Guidance literature:

Product distribution; microbal transformation by seven streptomyces species;

DOI:10.1248/cpb.29.2313

upstream raw materials:

diazomethane

(2R,6'R)-7-chloro-4,6-dimethoxy-6'-methyl-spiro[benzofuran-2,1'-cyclohexane]-3,2',4'-trione

methanol

sodium ethanolate

Downstream raw materials:

griseofulvin

griseofulvin

Refernces

• 1、 Tomozane,Takeuchi,Choshi,Kishida,Yamato. "Syntheses and antifungal activities of dl-griseofulvin and its congeners. I". . p. 925 - 929. Retrieved 2007/10/02.
• 2、 Oda,Sato. "Stereospecific incorporation of hydrogen from reduced nicotinamide adenine dinucleotide phosphate in hydrogenation of (-)-dehydrogriseofulvin to (+)-griseofulvin by a partially purified enzyme system of Streptomyces cinereocrocatus". . p. 4635 - 4640. Retrieved 2007/10/02.