Citromycetin

Base Information

• Chemical Name: Citromycetin
• CAS No.: 478-60-4
• Molecular Formula: C₁₄H₁₀O₇
• Molecular Weight: 290.229
• NSC Number: 53584
• UNII: 6LQ9JP1YA7
• DSSTox Substance ID: DTXSID60197283
• Nikkaji Number: J6.149B
• Wikipedia: Citromycetin
• Wikidata: Q15410873
• Mol file: 478-60-4.mol

Synonyms:citromycetin

Chemical Property of Citromycetin

Chemical Property:

• Vapor Pressure: 8.16E-19mmHg at 25°C
• Boiling Point: 669.1°Cat760mmHg
• Flash Point: 260.9°C
• PSA: 117.20000
• Density: 1.73g/cm³
• LogP: 1.61700
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 290.04265265
• Heavy Atom Count: 21
• Complexity: 562

Purity/Quality:

99% ^*data from raw suppliers

Citromycetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C2=C(O1)C3=C(C=C(C(=C3C(=O)O)O)O)OC2
• Uses: Citromycetin was independently isolated and named from a number of different fungal species during the 1930s to 1950s and subsequently shown to be identical. Citromycetin is active against Gram positive bacteria. NCI studies demonstrated the lack of activity against tumours and AIDS. Citromycetin is an interesting metabolite which has received little attention in modern times. Citromycetin is an antibacterial reagent active against Gram positive bacteria.

Technology Process of Citromycetin

There total 9 articles about Citromycetin 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: 69.0%

O,O-dimethylcitromycetin (101905-34-4) → Citromycetin (478-60-4)

Guidance literature:

With aluminium trichloride; dimethylsulfide; In dichloromethane; for 15h; Ambient temperature;

DOI:10.1039/P19870000395

Reference yield: 64.0%

→ Citromycetin (478-60-4)

Guidance literature:

With hydrogenchloride; In methanol; for 240h; Ambient temperature;

DOI:10.1039/P19880000763

Reference yield:

8,9-dimethoxy-2-methyl-10-(prop-1-enyl)pyrano<3,2-c><1>-benzopyran-4(5H)-one (101905-32-2) → Citromycetin (478-60-4)

Guidance literature:

Multi-step reaction with 3 steps

1: O₃, Oil Violet

2: sodium chlorite, sulphamic acid

3: 69 percent / AlCl₃, Me₂S / CH₂Cl₂

With sodium chlorite; aluminium trichloride; dimethylsulfide; oil violet; aminosulfonic acid; ozone; In dichloromethane;

DOI:10.1039/c39850001483

upstream raw materials:

O,O-dimethylcitromycetin

8,9-dimethoxy-2-methyl-10-(prop-1-enyl)pyrano<3,2-c><1>-benzopyran-4(5H)-one

8,9-dimethoxy-2-methyl-4-oxo-4H,5H-pyrano<3,2-c><1>-benzopyran-10-carbaldehyde

3-chloromethyl-2-<6-hydroxy-3,4-dimethoxy-2-(prop-1-enyl)phenyl>-6-methyl-4H-pyran-4-one

Downstream raw materials:

citromycin

Refernces

• 1、 Demetriadou, Agathi K.,Laue, Ernest D.,Leeper, Finian J.,Staunton, James. "ISOLATION AND STRUCTURE ELUCIDATION OF POLIVIONE, A POLYKETIDE CO-METABOLITE OF CITROMYCETIN IN PENICILLIUM FREQUENTANS". . p. 763 - 768. Retrieved 1988.
• 2、 Yamauchi, Masashige,Katayama, Sadamu,Watanabe, Toshio. "Biogenetic-type Total Synthesis of Citromycetin". . p. 1483 - 1484. Retrieved 2007/10/02.