Pyocyanine

Base Information

• Chemical Name: Pyocyanine
• CAS No.: 85-66-5
• Molecular Formula: C13H10 N2 O
• Molecular Weight: 210.235
• Hs Code.: 2933990090
• European Community (EC) Number: 687-347-7
• NSC Number: 400612
• UNII: 9OQM399341
• DSSTox Substance ID: DTXSID9041108
• Nikkaji Number: J11.662I
• Wikipedia: Pyocyanin
• Wikidata: Q410503
• Metabolomics Workbench ID: 67039
• ChEMBL ID: CHEMBL2289232
• Mol file: 85-66-5.mol

Synonyms:Pyocyanin;Pyocyanine

Chemical Property of Pyocyanine

Chemical Property:

• Vapor Pressure: 1.03E-06mmHg at 25°C
• Melting Point: 133°
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 403.3°C at 760 mmHg
• PKA: 2.42±0.20(Predicted)
• Flash Point: 197.7°C
• PSA: 39.83000
• Density: 1.24g/cm³
• LogP: 2.35630
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 210.079312947
• Heavy Atom Count: 16
• Complexity: 420

Purity/Quality:

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

Pyocyanin from ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2N=C3C1=CC=CC3=O
• Description: Pyocyanine (85-66-5), a redox-active phenazine produced by?P. aeruginosa?and other pathogens, is an electron receptor, which stimulates redox cycling in bacteria as well as in a variety of human cell lines. It enhances oxidative metabolism, which increases the formation of intracellular reactive oxygen species (ROS) via reduction of NADPH. Pyocyanine accelerates neutrophil apoptosis?in vitro. Pyocyanine production by?P. aeruginosa?suppresses the acute inflammatory response by pathogen-driven acceleration of neutrophil apoptosis and associated reduction of local inflammation.
• Uses: Pyocyanin has been used:To disable the ability of forkhead box A2 (FOXA2) to regulate goblet cell hyperplasia and metaplasia (GCHM) and mucin expression.To activate nuclear factor (erythroid-derived 2)-like 2 (NRF2) through the reactive oxygen species (ROS)-inducible epidermal growth factor receptor (EGFR)-phosphoinositide 3-kinase (PI3K) cellular signal transduction pathway and its downstream effectors.To stimulate Pseudomonas aeruginosa PAO1 cell line adhesion and invasion in human lung carcinoma A549 cells via reactive oxygen species (ROS) production. Pyocyanin is an antibiotic accelerator of neutrophil apoptosis.

Technology Process of Pyocyanine

There total 9 articles about Pyocyanine 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: 97.0%

phenazine methosulfate (299-11-6) → pyocyanine (85-66-5)

Guidance literature:

With water; at 50 ℃; for 0.5h; Irradiation; Flow reactor;

DOI:10.1002/ejoc.201900526

Reference yield: 43.0%

N-methyl-1,2-phenylenediamine (4760-34-3) + 2-hydroxyresorcinol (87-66-1) → pyocyanine (85-66-5)

Guidance literature:

With oxygen; In isopropyl alcohol; at 20 ℃; for 48h; Reagent/catalyst; Darkness;

DOI:10.1021/acs.orglett.9b02601

Reference yield:

1,2-diamino-benzene (95-54-5) → pyocyanine (85-66-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C

2: oxygen / isopropyl alcohol / 48 h / 20 °C / Darkness

With oxygen; potassium carbonate; In N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/acs.orglett.9b02601

upstream raw materials:

phenazine methosulfate

Phenazin

2-nitro-N-phenylaniline

aniline

Downstream raw materials:

phenazin-1-yl acetate

1-Benzyloxyphenazin

formic acid

phenazin-1-ol

Refernces

• 1、 Kohatsu, Haruki,Kamo, Shogo,Tomoshige, Shusuke,Kuramochi, Kouji. "Total Syntheses of Pyocyanin, Lavanducyanin, and Marinocyanins A and B". supporting information. p. 7311 - 7314. Retrieved 2019/10/02.
• 2、 Borrero, Nicholas V.,Bai, Fang,Perez, Cristian,Duong, Benjamin Q.,Rocca, James R.,Jin, Shouguang,Huigens Iii, Robert W.. "Phenazine antibiotic inspired discovery of potent bromophenazine antibacterial agents against Staphylococcus aureus and Staphylococcus epidermidis". supporting information. p. 881 - 886. Retrieved 2014/02/14.