Cas no 25683-07-2 (Pyoluteorin)

Pyoluteorin is a secondary metabolite produced by certain strains of Pseudomonas bacteria, notably Pseudomonas fluorescens. It is a chlorinated polyketide antibiotic with notable antifungal and antibacterial properties, particularly against soil-borne plant pathogens such as Pythium and Rhizoctonia solani. Pyoluteorin exhibits a unique mode of action by disrupting membrane integrity and inhibiting cellular respiration in target organisms. Its selective activity makes it a valuable tool in studying microbial interactions and potential applications in agricultural biocontrol. The compound's stability under environmental conditions and low phytotoxicity further enhance its utility in sustainable crop protection strategies. Research continues to explore its biosynthesis and optimization for broader efficacy.
Pyoluteorin structure
Pyoluteorin structure
Product Name:Pyoluteorin
CAS No:25683-07-2
MF:C11H7Cl2NO3
MW:272.084181070328
CID:265456
PubChem ID:33137
Update Time:2025-06-09

Pyoluteorin Chemical and Physical Properties

Names and Identifiers

    • Methanone,(4,5-dichloro-1H-pyrrol-2-yl)(2,6-dihydroxyphenyl)-
    • Pyoluteorin
    • (4,5-dichloro-1H-pyrrol-2-yl)-(2,6-dihydroxyphenyl)methanone
    • (4,5-dichloro-pyrrol-2-yl)-(2,6-dihydroxy-phenyl)-ketone
    • (4,5-dichloro-pyrrol-2-yl)-(2,6-dihydroxy-phenyl)-methanone
    • (4,5-Dichlor-pyrrol-2-yl)-(2,6-dihydroxy-phenyl)-keton
    • AC1L1P15
    • BRN 0234664
    • KETONE, 4,5-DICHLOROPYRROL-2-YL 2,6-DIHYDROXYPHENYL
    • Methanone, (4,5-dichloro-1H-pyrrol-2-yl) (2,6-dihydroxyp
    • WLN: T5MJ BG CG EVR BQ FQ
    • Ketone,5-dichloropyrrol-2-yl 2,6-dihydroxyphenyl
    • (4, 5-dichloro-1H-pyrrol-2-yl)-(2, 6-dihydroxyphenyl)methanone
    • 4,5-di-chloro-2-(2',6'-dihydroxybenzoyl)-pyrrole
    • SCHEMBL11871902
    • NSC-143092
    • (4,5-Dichloro-1H-pyrrol-2-yl)(2,6-dihydroxyphenyl)methanone
    • NSC 143092
    • 2-(4,5-DICHLORO-1H-PYRROLE-2-CARBONYL)BENZENE-1,3-DIOL
    • 5-21-13-00199 (Beilstein Handbook Reference)
    • NSC143092
    • Methanone, (4,5-dichloro-1H-pyrrol-2-yl)(2,6-dihydroxyphenyl)-
    • AKOS025404653
    • SB63592
    • 4,5-dichloropyrrol-2-yl 2,6-dihydroxyphenylketone
    • HY-114979
    • Methanone,5-dichloro-1H-pyrrol-2-yl)(2,6-dihydroxyphenyl)-
    • 4,5-dichloropyrrol-2-yl 2,6-dihydroxyphenyl
    • DTXSID30180384
    • CHEBI:156453
    • J-016103
    • UNII-3YM4R964TU
    • 3YM4R964TU
    • 25683-07-2
    • CHEMBL2286204
    • CS-0064726
    • Methanone, (4,5-dichloro-1H-pyrrol-2-yl) (2,6-dihydroxyphenyl)-
    • Methanone,5-dichloro-1H-pyrrol-2-yl) (2,6-dihydroxyphenyl)-
    • G13042
    • DA-57256
    • DTXCID40102875
    • Methanone, (4,5-dichloro-1H-pyrrol-2-yl)(2,6-dihydroxyphenyl)-(9CI)
    • Ketone, 4,5-dichloropyrrol-2-yl 2,6-dihydroxyphenyl (7CI,8CI); Pyoluteorin (6CI); (4,5-Dichloro-1H-pyrrol-2-yl)(2,6-dihydroxyphenyl)methanone; 4,5-Dichloropyrrol-2-yl 2,6-dihydroxyphenylketone; NSC 143092
    • Inchi: 1S/C11H7Cl2NO3/c12-5-4-6(14-11(5)13)10(17)9-7(15)2-1-3-8(9)16/h1-4,14-16H
    • InChI Key: JPGWTZORMBTNMF-UHFFFAOYSA-N
    • SMILES: ClC1=C(C=C(C(C2C(=CC=CC=2O)O)=O)N1)Cl

Computed Properties

  • Exact Mass: 270.98041
  • Monoisotopic Mass: 270.98
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 2
  • Complexity: 292
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.8
  • Topological Polar Surface Area: 73.3A^2

Experimental Properties

  • Density: 1.4931 (rough estimate)
  • Boiling Point: 436.9°Cat760mmHg
  • Flash Point: 218°C
  • Refractive Index: 1.6140 (estimate)
  • PSA: 73.32
  • LogP: 2.96370

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Pyoluteorin Related Literature

Additional information on Pyoluteorin

Comprehensive Overview of Pyoluteorin (CAS No. 25683-07-2): Properties, Applications, and Research Insights

Pyoluteorin (CAS No. 25683-07-2) is a naturally occurring antibiotic compound produced by certain strains of Pseudomonas bacteria. This bioactive metabolite has garnered significant attention in agricultural and biomedical research due to its unique antimicrobial properties. The compound's molecular structure features a dichlorinated pyrrole ring linked to a resorcinol moiety, which contributes to its distinctive biological activity. Researchers have identified Pyoluteorin as a key player in microbial antagonism, particularly in the suppression of plant pathogens like Pythium and Rhizoctonia species.

In recent years, the search for sustainable alternatives to synthetic pesticides has driven renewed interest in Pyoluteorin. Agricultural scientists are exploring its potential as a biocontrol agent, especially in organic farming systems where chemical inputs are restricted. The compound's mode of action involves disruption of cell membrane integrity in target organisms, making it effective against a broad spectrum of fungal pathogens. Studies published in journals like Applied and Environmental Microbiology have demonstrated that Pyoluteorin-producing Pseudomonas strains can significantly reduce damping-off diseases in crops such as cotton and wheat.

The pharmaceutical potential of Pyoluteorin (CAS No. 25683-07-2) has also become a hot topic in drug discovery circles. Its structural similarity to clinically important antibiotics has prompted investigations into its antimicrobial spectrum against drug-resistant bacteria. Molecular docking studies suggest that the compound may interfere with bacterial protein synthesis, though the exact mechanism remains under investigation. This research aligns with current global concerns about antimicrobial resistance (AMR), making Pyoluteorin a subject of interest for researchers seeking novel antibiotic scaffolds.

From an ecological perspective, the production of Pyoluteorin by soil bacteria represents a fascinating example of microbial chemical warfare. The compound's biosynthesis is regulated by complex quorum-sensing mechanisms, which have become model systems for studying bacterial communication. Recent advances in synthetic biology have enabled researchers to engineer optimized production strains, addressing previous challenges related to low natural yields of Pyoluteorin. These developments are particularly relevant given the growing demand for fermentation-derived bioactive compounds.

Analytical characterization of Pyoluteorin typically involves HPLC-MS techniques, with the compound showing strong UV absorption at 254 nm. The CAS registry (No. 25683-07-2) provides standardized information about its chemical identity, including molecular formula (C11H7Cl2NO3) and weight (272.08 g/mol). Stability studies indicate that the compound is photosensitive, requiring storage in amber vials at -20°C for long-term preservation. These physicochemical properties are crucial for researchers working with Pyoluteorin in both laboratory and field applications.

Emerging applications of Pyoluteorin extend to microbiome research, where scientists are investigating its role in shaping microbial communities in the rhizosphere. The compound's selective activity against certain microorganisms while sparing others makes it an interesting tool for manipulating soil microbiomes. This application gains importance in the context of climate-smart agriculture, where microbial solutions are being sought to enhance crop resilience. Recent field trials have shown promising results when Pyoluteorin-producing bacteria are used as seed treatments, reducing the need for conventional fungicides.

Quality control standards for Pyoluteorin (CAS No. 25683-07-2) have become more stringent as its commercial potential grows. Analytical reference standards now typically specify ≥95% purity by HPLC, with strict limits on residual solvents and heavy metals. These specifications ensure reproducibility in research applications and facilitate regulatory approval for agricultural uses. The compound's environmental fate has also been studied, with data showing moderate persistence in soil (half-life of 10-14 days under typical conditions) and low mobility in water systems.

Future research directions for Pyoluteorin include structure-activity relationship studies to develop derivatives with improved properties. Semi-synthetic modifications of the core structure aim to enhance stability, reduce phytotoxicity, and expand the antimicrobial spectrum. Such efforts align with the growing trend toward "green chemistry" approaches in agrochemical development. Additionally, genomic studies of Pyoluteorin biosynthetic gene clusters may reveal new enzymatic pathways for biocatalysis applications.

For researchers sourcing Pyoluteorin, it's important to verify the CAS No. 25683-07-2 when comparing products from different suppliers. The compound is commercially available as a purified standard for research purposes, typically in milligram to gram quantities. Storage recommendations generally advise protection from light and moisture, with some formulations including stabilizers for extended shelf life. These practical considerations are essential for ensuring experimental consistency in studies involving this biologically active compound.

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