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 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

Cook, RJ; Thomashow, LS; Weller, DM; Fujimoto, D; Mazzola, M; Bangera, G; Kim, DS (May 1995). "Molecular mechanisms of defense by rhizobacteria against root disease". Proceedings of the National Academy of Sciences of the United States of America. 92 (10): 4197–4201. Bibcode:1995PNAS...92.4197C. doi:10.1073/pnas.92.10.4197. PMC 41910. PMID 11607544.
Duffy, BK; Défago, G (June 1999). "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. PMC 91358. PMID 10347023.
Achkar, J; Xian, M; Zhao, H; Frost, JW (April 2005). "Biosynthesis of phloroglucinol". Journal of the American Chemical Society. 127 (15): 5332–5333. doi:10.1021/ja042340g. PMID 15826166.
Bangera, MG; Thomashow, LS (May 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): 3155–3163. 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 (April 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): 1357–1361. Bibcode:1997ApEnM..63.1357C. doi:10.1128/AEM.63.4.1357-1361.1997. PMC 1389549. PMID 16535571.
Ramette, A; Frapolli, M; Fischer-Le Saux, M; Gruffaz, C; Meyer, JM; Défago, G; et al. (May 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; Défago, G (April 2005). "Biological control of soil-borne pathogens by fluorescent pseudomonads". Nature Reviews. Microbiology. 3 (4): 307–319. doi:10.1038/nrmicro1129. PMID 15759041. S2CID 18469703.
Brucker, RM; Baylor, CM; Walters, RL; Lauer, A; Harris, RN; Minbiole, KP (January 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.
Garagulia, AD; Kiprianova, EA; Boĭko, OI (1974). "[Antibiotic action of bacteria of the genus Pseudomonas on phytopathogenic fungi]". Mikrobiolohichnyi Zhurnal (in Ukrainian). 36 (2): 197–202. OCLC 1063241398. PMID 4465652.
Pidoplichko, VN; Garagulya, AD (1974). "[Effect of antagonistic bacteria on development of wheat root rot]". Zhurnal Mikrobiologii (in Ukrainian). Kyiv. 36: 599–602. ISSN 1028-0987. OCLC 1063241398.

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[Cook-et-al-1995-1] Cook, RJ; Thomashow, LS; Weller, DM; Fujimoto, D; Mazzola, M; Bangera, G; Kim, DS (May 1995). "Molecular mechanisms of defense by rhizobacteria against root disease". Proceedings of the National Academy of Sciences of the United States of America. 92 (10): 4197–4201. Bibcode:1995PNAS...92.4197C. doi:10.1073/pnas.92.10.4197. PMC 41910. PMID 11607544.

[Duffy-Defago-1999-2] Duffy, BK; Défago, G (June 1999). "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. PMC 91358. PMID 10347023.

[3] Achkar, J; Xian, M; Zhao, H; Frost, JW (April 2005). "Biosynthesis of phloroglucinol". Journal of the American Chemical Society. 127 (15): 5332–5333. doi:10.1021/ja042340g. PMID 15826166.

[4] Bangera, MG; Thomashow, LS (May 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): 3155–3163. 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 (April 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): 1357–1361. Bibcode:1997ApEnM..63.1357C. doi:10.1128/AEM.63.4.1357-1361.1997. PMC 1389549. PMID 16535571.

[Ramette-6] Ramette, A; Frapolli, M; Fischer-Le Saux, M; Gruffaz, C; Meyer, JM; Défago, G; et al. (May 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; Défago, G (April 2005). "Biological control of soil-borne pathogens by fluorescent pseudomonads". Nature Reviews. Microbiology. 3 (4): 307–319. doi:10.1038/nrmicro1129. PMID 15759041. S2CID 18469703.

[Brucker_et_al._2008-8] Brucker, RM; Baylor, CM; Walters, RL; Lauer, A; Harris, RN; Minbiole, KP (January 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] Garagulia, AD; Kiprianova, EA; Boĭko, OI (1974). "[Antibiotic action of bacteria of the genus Pseudomonas on phytopathogenic fungi]". Mikrobiolohichnyi Zhurnal (in Ukrainian). 36 (2): 197–202. OCLC 1063241398. PMID 4465652.

[Pidoplichko-Garagulya-1974-10] Pidoplichko, VN; Garagulya, AD (1974). "[Effect of antagonistic bacteria on development of wheat root rot]". Zhurnal Mikrobiologii (in Ukrainian). Kyiv. 36: 599–602. ISSN 1028-0987. OCLC 1063241398.