2,4-Diacetylphloroglucinol

UsesDiacetylphloroglucinol (DAPG) is a small molecular weight, phenolic metabolite belonging to the phloroglucinol (1,3,5- trihydroxybenzene) family produced by bacteria, including Pseudomonas strains. DAPG exhibits a broad range of biological activities, albeit with mostly low potency. In the search for novel actives, DAPG 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.

PreparationPreparation by Friedel–Crafts acylation of phloroglucinol, with acetic acid, – by using boron trifluoride-acetic acid complex at 28–30° for 18 h (85%)with acetic anhydride, – in the presence of boron trifluoride-ethyl ether complex at 20° for 1 h (80%) – in the presence of zinc chloride at 145–150° for 15 min (25%); – in the presence of concentrated sulfuric acid (24%) with acetyl chloride, – (4 equiv.) in the presence of ferric chloride – in ethyl ether in the presence of aluminium chloride at r.t. for 5 days (8).