pyoluteorin
- Product Name
- pyoluteorin
- CAS No.
- 25683-07-2
- Chemical Name
- pyoluteorin
- Synonyms
- pyoluteorin;Pyoluteorin, 10 mM in DMSO;4,5-Dichloro-1H-pyrrol-2-yl 2,6-dihydroxyphenyl ketone;(4,5-Dichloro-1H-pyrrol-2-yl)(2,6-dihydroxyphenyl)methanone;Methanone, (4,5-dichloro-1H-pyrrol-2-yl)(2,6-dihydroxyphenyl)-
- CBNumber
- CB71336800
- Molecular Formula
- C11H7Cl2NO3
- Formula Weight
- 272.08
- MOL File
- 25683-07-2.mol
pyoluteorin Property
- Melting point:
- 174-175 °C (decomp)
- Boiling point:
- 436.9±45.0 °C(Predicted)
- Density
- 1.4931 (rough estimate)
- refractive index
- 1.6140 (estimate)
- storage temp.
- Store at -20°C
- solubility
- Soluble in DMSO
- form
- solid
- pka
- 6.97±0.35(Predicted)
- color
- White to off-white
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H301Toxic if swalloed
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P321Specific treatment (see … on this label).
P330Rinse mouth.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- 19457
- Product name
- Pyoluteorin
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $239
- Updated
- 2024/03/01
- Product number
- 19457
- Product name
- Pyoluteorin
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $777
- Updated
- 2024/03/01
- Product number
- P840375
- Product name
- Pyoluteorin
- Packaging
- 25mg
- Price
- $1455
- Updated
- 2021/12/16
- Product number
- 52866
- Product name
- Pyoluteorin
- Packaging
- 100mg
- Price
- $2200
- Updated
- 2021/12/16
- Product number
- C4039
- Product name
- Pyoluteorin
- Packaging
- 5mg
- Price
- $1351
- Updated
- 2021/12/16
pyoluteorin Chemical Properties,Usage,Production
Uses
Pyoluteorin is a small chlorinated pyrrol produced by several species of Pseudomonas, first reported in 1958. Pyoluteorin exhibits a broad bioprofile, demonstrating antibiotic, antifungal and herbicidal activity. More recently, pyoluteorin has been investigated as bio-pesticide and has been shown to modulate the levels of metabolites in Pseudomonas.
Definition
ChEBI: Pyoluteorin is a member of the class of resorcinols that is resorcinol in which the hydrogen at position 2 is replaced by a 4,5-dichloro-1H-pyrrole-2-carbonyl group. It is a natural product found in Pseudomonas fluorescens which exhibits antibacterial properties and is a strong inducer of caspase-3-dependent apoptosis. It has a role as a bacterial metabolite, an apoptosis inducer, an antifungal agent, a marine metabolite and an antibacterial agent. It is a member of resorcinols, a member of pyrroles, an organochlorine compound, a diol, a beta-hydroxy ketone, a polyketide, an aromatic ketone and an organochlorine pesticide.
Biological Activity
pyoluteorin is a secondary metabolite produced by the biological control organism pseudomonas fluorescens pf-5, a rhizosphere bacterium. pyoluteorin shows no toxicity to seed- and root-rotting plant pathogens. pyoluteorin production is influenced by positive autoregulation. addition of pyoluteorin to liquid cultures of pf-5 enhanced pyoluteorin production.pyoluteorin functions as a signal molecule negatively regulating additional secondary metabolites produced by pseudomonas [1]. the pyoluteorin contributes to the biological control of soilborne plant diseases by some strains of pseudomonas fluorescens, including pf-5. pyoluteorin induces its own productionand represses the other’s production [2]. depending on the plant, pyoluteorin production plays an important role in the suppression of damping-off by strain cha0 without being a major mechanism in disease suppression [3].
Safety Profile
A poison by ingestion and intraperitoneal routes. A flammable liquid. When heated to decomposition it emits toxic vapors of NOx and Cl-.
References
[1] brodhagen m, henkels m d, loper j e. positive autoregulation and signaling properties of pyoluteorin, an antibiotic produced by the biological control organism pseudomonas fluorescens pf-5[j]. applied and environmental microbiology, 2004, 70(3): 1758-1766.
[2] kidarsa t a, goebel n c, zabriskie t m, et al. phloroglucinol mediates cross‐talk between the pyoluteorin and 2, 4‐diacetylphloroglucinol biosynthetic pathways in pseudomonas fluorescens pf‐5[j]. molecular microbiology, 2011, 81(2): 395-414.
[3] maurhofer m, keel c, haas d, et al. pyoluteorin production bypseudomonas fluorescens strain cha0 is involved in the suppression ofpythium damping-off of cress but not of cucumber[j]. european journal of plant pathology, 1994, 100(3): 221-232.
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