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 (Jmol)	Interactive image
ChEBI	CHEBI:78688
ChEMBL	ChEMBL276139
ChemSpider	15687
ECHA InfoCard	100.168.316
PubChem	16547
UNII	8XV4YYO3WN
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).
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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

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.
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: 180–188. doi:10.1016/j.syapm.2010.10.005.
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.
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.