Aspergillic acid

Base Information

• Chemical Name: Aspergillic acid
• CAS No.: 490-02-8
• Molecular Formula: C₁₂H₂₀N₂O₂
• Molecular Weight: 224.303
• NSC Number: 22939
• UNII: OP8S9B694G
• DSSTox Substance ID: DTXSID10871687
• Nikkaji Number: J12.576H
• Wikipedia: Aspergillic_acid
• Wikidata: Q4807880
• Metabolomics Workbench ID: 67595
• ChEMBL ID: CHEMBL4297021
• Mol file: 490-02-8.mol

Synonyms:6-sec-butyl-1-hydroxy-3-isobutyl-2(1H)-pyrazinone;aspergillic acid

Chemical Property of Aspergillic acid

Chemical Property:

• Vapor Pressure: 7.8E-06mmHg at 25°C
• Melting Point: 97-99° (methanol)
• Refractive Index: 1.4760 (estimate)
• Boiling Point: 336.3°Cat760mmHg
• PKA: 5.5(at 25℃)
• Flash Point: 157.2°C
• PSA: 58.58000
• Density: 1.1g/cm³
• LogP: 2.92770
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 224.152477885
• Heavy Atom Count: 16
• Complexity: 332

Purity/Quality:

99%, ^*data from raw suppliers

ASPERGILLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C1=CN=C(C(=O)N1O)CC(C)C
• Uses: Antibiotic.

Technology Process of Aspergillic acid

There total 5 articles about Aspergillic 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: 86.0%

2-chloro-3-isobutyl-6-sec-butylpyrazine 1-oxide (86044-70-4) → dl-aspergillic acid (490-02-8,21634-79-7)

Guidance literature:

With potassium hydroxide; In methanol; for 2h; Heating;

DOI:10.1248/cpb.31.20

Reference yield: 9.0%

2-chloro-3-isobutyl-6-sec-butylpyrazine 1-oxide (86044-70-4) → 2-chloro-3-isobutyl-6-(α-hydroxy)-sec-butylpyrazine 1-oxide + dl-hydroxyaspergillic acid (19833-47-7) + dl-aspergillic acid (490-02-8,21634-79-7)

Guidance literature:

With oxygen; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 5h;

DOI:10.1248/cpb.31.20

Reference yield:

3-chloro-5-(1-methylpropyl)-2-(2-methylpropyl)pyrazine (86044-66-8) → dl-aspergillic acid (490-02-8,21634-79-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / K₂S₂O₈ / H₂SO₄ / 24 h / Ambient temperature

2: 86 percent / 20percent KOH / methanol / 2 h / Heating

With potassium hydroxide; dipotassium peroxodisulfate; In methanol; sulfuric acid;

DOI:10.1248/cpb.31.20

upstream raw materials:

2-chloro-3-isobutyl-6-sec-butylpyrazine 1-oxide

3-chloro-5-(1-methylpropyl)-2-(2-methylpropyl)pyrazine

DL-isoleucyl-leucyl anhydride

Refernces