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 ;
	show InChI
	show SMILES
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).
	(what is ?)
	Infobox references

2,4-Diacetylphloroglucinol or Phl^[1]^[2] is a natural phenol found in several bacteria:

Specific strains of the Gram-negative bacterium Pseudomonas fluorescens.^[3] This compound is found to be responsible for the antiphytopathogenic^[4] and biocontrol^[5] properties in these strains.
It is also found in Pseudomonas protegens, where it has the same activity against various plant pathogens.^[6]^[7]
Lysobacter gummosus, a bacterium which lives on the skin of red-backed salamanders.^[8]
Isolates of Pseudomonas aurantiaca found in Ukraine, living in root symbiosis produce it to control Fusarium oxysporum.^[9]^[10]^[1]

References[]

^ Jump up to: ^a ^b Cook, R. J.; Thomashow, L. S.; Weller, D. M.; Fujimoto, D.; Mazzola, M.; Bangera, G.; Kim, D. S. (1995-05-09). "Molecular mechanisms of defense by rhizobacteria against root disease". Proceedings of the National Academy of Sciences. 92 (10): 4197–4201. Bibcode:1995PNAS...92.4197C. doi:10.1073/pnas.92.10.4197. ISSN 0027-8424. PMC 41910. PMID 11607544.
^ Duffy, Brion K.; Défago, Geneviève (1999-06-01). "Environmental Factors Modulating Antibiotic and Siderophore Biosynthesis by Pseudomonas fluorescens Biocontrol Strains". Applied and Environmental Microbiology. 65 (6): 2429–2438. Bibcode:1999ApEnM..65.2429D. doi:10.1128/aem.65.6.2429-2438.1999. ISSN 1098-5336. PMC 91358. PMID 10347023.
^ 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. doi:10.1128/JB.181.10.3155-3163.1999. 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. Bibcode:1997ApEnM..63.1357C. doi:10.1128/AEM.63.4.1357-1361.1997. 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. S2CID 18469703.
^ 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. S2CID 27149357.
^ A. D. Garagulya, E. A. Kipmanova, and O. I. Boiko (1974). [Antibiotic effect of bacteria from the genus Pseudomonas on phytopathogenic fungi] |trans-title= requires |title= or |script-title= (help). . Kyiv. 36: 197–202. ISSN 1028-0987. OCLC 1063241398.CS1 maint: multiple names: authors list (link)
^ V. N. Pidoplichko, A. D. Garagulya (1974). [Effect of antagonistic bacteria on development of wheat root rot] |trans-title= requires |title= or |script-title= (help). . Kyiv. 36: 599–602. ISSN 1028-0987. OCLC 1063241398.

This article about an aromatic compound is a stub. You can help Wikipedia by .

[Cook-et-al-1995-1] Jump up to: ^a ^b Cook, R. J.; Thomashow, L. S.; Weller, D. M.; Fujimoto, D.; Mazzola, M.; Bangera, G.; Kim, D. S. (1995-05-09). "Molecular mechanisms of defense by rhizobacteria against root disease". Proceedings of the National Academy of Sciences. 92 (10): 4197–4201. Bibcode:1995PNAS...92.4197C. doi:10.1073/pnas.92.10.4197. ISSN 0027-8424. PMC 41910. PMID 11607544.

[Duffy-Defago-1999-2] Duffy, Brion K.; Défago, Geneviève (1999-06-01). "Environmental Factors Modulating Antibiotic and Siderophore Biosynthesis by Pseudomonas fluorescens Biocontrol Strains". Applied and Environmental Microbiology. 65 (6): 2429–2438. Bibcode:1999ApEnM..65.2429D. doi:10.1128/aem.65.6.2429-2438.1999. ISSN 1098-5336. PMC 91358. PMID 10347023.

[3] 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.

[4] 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. doi:10.1128/JB.181.10.3155-3163.1999. PMC 93771. PMID 10322017.

[5] 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. Bibcode:1997ApEnM..63.1357C. doi:10.1128/AEM.63.4.1357-1361.1997. PMC 1389549. PMID 16535571.

[Ramette-6] 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.

[7] 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. S2CID 18469703.

[Brucker_et_al._2008-8] 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. S2CID 27149357.

[Garagulya-et-al-1974-9] A. D. Garagulya, E. A. Kipmanova, and O. I. Boiko (1974). [Antibiotic effect of bacteria from the genus Pseudomonas on phytopathogenic fungi] |trans-title= requires |title= or |script-title= (help). . Kyiv. 36: 197–202. ISSN 1028-0987. OCLC 1063241398.CS1 maint: multiple names: authors list (link)

[Pidoplichko-Garagulya-1974-10] V. N. Pidoplichko, A. D. Garagulya (1974). [Effect of antagonistic bacteria on development of wheat root rot] |trans-title= requires |title= or |script-title= (help). . Kyiv. 36: 599–602. ISSN 1028-0987. OCLC 1063241398.

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