2161-87-7

Beige Needles

Triacetylphloroglucinol (TAPG) is the most hydrophobic of a small molecular weight phenolic metabolite belonging to the phloroglucinol (1,3,5 trihydroxybenzene) family, produced by bacteria including Pseudomonas strains. TAPG exhibits a broad range of biological activities, albeit with mostly low potency. In the search for novel actives, TAPG and related metabolites are important for dereplication to eliminate leads due to high amounts of weakly potent actives. Although weakly active, this family appears to be important in the biocontrol of plant diseases by some Pseudomonas strains.

Triacetylphloroglucinol is a C₃-symmetric tritopic bridging ligand. It has been used in the synthesis of various compounds, including trinuclear vanadium Schiff base complexes, copper complexes, and anthelmintics.

Obtained by Friedel–Crafts acylation of phloroglucinol,
? with acetic anhydride in the presence of boron trifluoride in acetic acid at r.t. (60%)
; ? with acetyl chloride in the presence of aluminium chloride in ethyl ether at r.t. for 6 days (17%)
; ? with acetyl chloride and acetic acid in the presence of ferric chloride in ethyl acetate.

[1] EIKE T. SPIELBERG  Winfried P. 2,4,6-Triacetylphlorogucinol as Threefold Symmetric Bridging Ligand: Synthesis, Structure and Magnetic Properties of the Copper Complex[J]. European Journal of Inorganic Chemistry, 2010, 2010 20: 3093-3096. DOI: 10.1002/ejic.201000341
[2] PAULSAMY SURESH . Asymmetric sulfoxidation of prochiral sulfides using aminoalcohol derived chiral C3-symmetric trinuclear vanadium Schiff base complexes[J]. Tetrahedron, asymmetry, 2007, 18 23: Pages 2820-2827. DOI: 10.1016/j.tetasy.2007.11.005
[3] K. BOWDEN  W. J R  J L BROADBENT. SOME SIMPLE ANTHELMINTICS[J]. British Journal of Pharmacology, 1965, 24 3: 714-724. DOI: 10.1111/j.1476-5381.1965.tb01627.x