2,4-Diacetylphloroglucinol

2,4-Diacetylphloroglucinol
Names
	Preferred IUPAC name 1,1'-(2,4,6-Trihydroxy-1,3-phenylene)di(ethan-1-one)
	Other names 1-(3-Acetyl-2,4,6-trihydroxyphenyl)ethanone; 2,4-DAPG
Identifiers
CAS Number	2161-86-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:78688 ;
ChEMBL	ChEMBL276139 ;
ChemSpider	15687 ;
ECHA InfoCard	100.168.316
PubChem CID	16547;
UNII	8XV4YYO3WN ;
CompTox Dashboard (EPA)	DTXSID10175995 ;
	InChI InChI=1S/C10H10O5/c1-4(11)8-6(13)3-7(14)9(5(2)12)10(8)15/h3,13-15H,1-2H3 Key: PIFFQYJYNWXNGE-UHFFFAOYSA-N ;
	SMILES CC(=O)C1=C(C(=C(C=C1O)O)C(=O)C)O;
Properties
Chemical formula	C10H10O5
Molar mass	210.18 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

2,4-Diacetylphloroglucinol is a natural phenol found in specific strains of the Gram-negative bacterium Pseudomonas fluorescens.[1] This compound is found to be responsible for the antiphytopathogenic[2] and biocontrol[3] properties in these strains. It is also found in Pseudomonas protegens, where it has the same activity against various plant pathogens.[4][5]

2,4-Diacetylphloroglucinol is also produced by Lysobacter gummosus, a bacterium which lives on the skin of red-backed salamanders.[6]

References

Achkar, Jihane; Xian, Mo; Zhao, Huimin; Frost, J. W. (2005). "Biosynthesis of Phloroglucinol". J. Am. Chem. Soc. 127 (15): 5332–5333. doi:10.1021/ja042340g. PMID 15826166.
Bangera, MG; Thomashow, LS (1999). "Identification and characterization of a gene cluster for synthesis of the polyketide antibiotic 2,4-diacetylphloroglucinol from Pseudomonas fluorescens Q2-87". Journal of Bacteriology. 181 (10): 3155–63. PMC 93771. PMID 10322017.
Cronin, D; Moenne-Loccoz, Y; Fenton, A; Dunne, C; Dowling, DN; O'Gara, F (1997). "Role of 2,4-Diacetylphloroglucinol in the Interactions of the Biocontrol Pseudomonad Strain F113 with the Potato Cyst Nematode Globodera rostochiensis". Applied and Environmental Microbiology. 63 (4): 1357–61. PMC 1389549. PMID 16535571.
Ramettea, Alban; Frapollia, Michele; Fischer-Le Saux, Marion; Gruffaz, C.; Meyer, Jean-Marie; Défago, Geneviève; Sutra, Laurent; Moënne-Loccoz, Yvan (2011). "Pseudomonas protegens sp. nov., widespread plant-protecting bacteria producing the biocontrol compounds 2,4-diacetylphloroglucinol and pyoluteorin". Systematic and Applied Microbiology. 34 (3): 180–188. doi:10.1016/j.syapm.2010.10.005. PMID 21392918.
Haas, D.; Defago, G. (2005). "Biological control of soil-borne pathogens by fluorescent pseudomonads". Nature Reviews Microbiology. 3 (4): 307–19. doi:10.1038/nrmicro1129. PMID 15759041.
Brucker, R.M.; Baylor, C.M.; Walters, R.L.; Lauer, A.; Harris, R.N.; Minbiole, K.P.C. (2008). "The identification of 2,4-diacetylphloroglucinol as an antifungal metabolite produced by cutaneous bacteria of the salamander Plethodon cinereus". Journal of Chemical Ecology. 34 (1): 39–43. doi:10.1007/s10886-007-9352-8. PMID 18058176.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Achkar, Jihane; Xian, Mo; Zhao, Huimin; Frost, J. W. (2005). "Biosynthesis of Phloroglucinol". J. Am. Chem. Soc. 127 (15): 5332–5333. doi:10.1021/ja042340g. PMID 15826166.

[2] Bangera, MG; Thomashow, LS (1999). "Identification and characterization of a gene cluster for synthesis of the polyketide antibiotic 2,4-diacetylphloroglucinol from Pseudomonas fluorescens Q2-87". Journal of Bacteriology. 181 (10): 3155–63. PMC 93771. PMID 10322017.

[3] Cronin, D; Moenne-Loccoz, Y; Fenton, A; Dunne, C; Dowling, DN; O'Gara, F (1997). "Role of 2,4-Diacetylphloroglucinol in the Interactions of the Biocontrol Pseudomonad Strain F113 with the Potato Cyst Nematode Globodera rostochiensis". Applied and Environmental Microbiology. 63 (4): 1357–61. PMC 1389549. PMID 16535571.

[Ramette-4] Ramettea, Alban; Frapollia, Michele; Fischer-Le Saux, Marion; Gruffaz, C.; Meyer, Jean-Marie; Défago, Geneviève; Sutra, Laurent; Moënne-Loccoz, Yvan (2011). "Pseudomonas protegens sp. nov., widespread plant-protecting bacteria producing the biocontrol compounds 2,4-diacetylphloroglucinol and pyoluteorin". Systematic and Applied Microbiology. 34 (3): 180–188. doi:10.1016/j.syapm.2010.10.005. PMID 21392918.

[5] Haas, D.; Defago, G. (2005). "Biological control of soil-borne pathogens by fluorescent pseudomonads". Nature Reviews Microbiology. 3 (4): 307–19. doi:10.1038/nrmicro1129. PMID 15759041.

[Brucker_et_al._2008-6] Brucker, R.M.; Baylor, C.M.; Walters, R.L.; Lauer, A.; Harris, R.N.; Minbiole, K.P.C. (2008). "The identification of 2,4-diacetylphloroglucinol as an antifungal metabolite produced by cutaneous bacteria of the salamander Plethodon cinereus". Journal of Chemical Ecology. 34 (1): 39–43. doi:10.1007/s10886-007-9352-8. PMID 18058176.