Usnic acid

Base Information

• Chemical Name: Usnic acid
• CAS No.: 125-46-2
• Deprecated CAS: 11024-93-4,17669-01-1,21987-06-4,596-41-8,1946-70-9,510-03-2,1946-70-9,596-41-8
• Molecular Formula: C18H16O7
• Molecular Weight: 344.321
• Hs Code.: 2917399090
• European Community (EC) Number: 204-740-7
• NSC Number: 8517,5890,5889
• DSSTox Substance ID: DTXSID0040123
• Nikkaji Number: J5.374K
• Wikipedia: Usnic_acid
• Wikidata: Q27105599
• Metabolomics Workbench ID: 123394
• ChEMBL ID: CHEMBL1375951
• Mol file: 125-46-2.mol

Synonyms:2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzofurandione;usnic acid

Chemical Property of Usnic acid

Chemical Property:

• Vapor Pressure: 3E-15mmHg at 25°C
• Melting Point: 200 °C
• Refractive Index: 495 ° (C=0.7, CHCl3)
• Boiling Point: 594.8 °C at 760 mmHg
• PKA: 4.00±0.40(Predicted)
• Flash Point: 219.1 °C
• PSA: 117.97000
• Density: 1.49 g/cm³
• LogP: 1.49980
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 344.08960285
• Heavy Atom Count: 25
• Complexity: 708

Purity/Quality:

99%, ^*data from raw suppliers

Usnic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R22:
• Hazard Codes: T,N
• Statements: 25-50/53
• Safety Statements: 22-24/25-61-60-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Preservatives
• Canonical SMILES: CC1=C(C(=C2C(=C1O)C3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O
• Uses: Usnic acid is an enzyme inhibiting antitumor agent. antibacterial Usnic acid is a major metabolite from a number of lichen and fungal species and is perhaps one of the longest known microbial metabolites, first isolated in 1844. Usnic acid exhibits a broad range of biological activity, indeed it is easier to list the bioassays in which it does not exhibit activity. More often than not, potency is low and of limited value. Usnic acid is an important metabolite for dereplication in discovery research programs.

Technology Process of Usnic acid

There total 1 articles about Usnic acid 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:

→ usnic acid (125-46-2)

Guidance literature:

(-)-Usninsaeure, sd. Xylol;

Reference yield: 59.0%

usnic acid (125-46-2) + phenylhydrazine (100-63-0) → 8-acetyl-5,7-dihydroxy-3,4a,6-trimethyl-1-phenyl-1,4a-dihydro-4H-benzofuro[3,2-f]indazol-4-one (62495-85-6,71368-50-8,906636-30-4)

Guidance literature:

In ethanol; for 3h; Reflux; Inert atmosphere;

DOI:10.1021/acs.jnatprod.8b00980

Reference yield: 47.0%

usnic acid (125-46-2) + p-tolylhydrazine hydrochloride (637-60-5,35467-65-3) → 8-acetyl-5,7-dihydroxy-3,4a,6-trimethyl-1-(p-tolyl)-1,4a-dihydro-4H-benzofuro[3,2-f]indazol-4-one

Guidance literature:

With pyridine; In ethanol; for 16h; Reflux; Inert atmosphere;

DOI:10.1021/acs.jnatprod.8b00980

Downstream raw materials:

8-acetyl-5,7-dihydroxy-3,4a,6-trimethyl-1-phenyl-1,4a-dihydro-4H-benzofuro[3,2-f]indazol-4-one