2',4',6'-Trihydroxyacetophenone monohydrate

Chemical properties

Light Brown Solid

The Uses of 2',4',6'-Trihydroxyacetophenone monohydrate

Induced choleresis in rats is mediated through multidrug resistance protein-2 (Mrp2). It enhances bile secretion

The Uses of 2',4',6'-Trihydroxyacetophenone monohydrate

Monoacetylphloroglucinol (MAPG) is small molecular weight phenolic metabolite belonging to the phloroglucinol (1,3,5-trihydroxybenzene) family, produced by bacteria including Pseudomonas strains. MAPG exhibits a broad range of biological activity albeit with mostly low potency. In the search for novel actives, MAPG and related metabolites are important metabolites 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.

The Uses of 2',4',6'-Trihydroxyacetophenone monohydrate

Induced choleresis in rats is mediated through multidrug resistance protein-2 (Mrp2). It enhances bile secretion.

Definition

ChEBI: A benzenetriol that is acetophenone in which the hydrogens at positions 2, 4, and 6 on the phenyl group are replaced by hydroxy groups. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of acid c glycans and glycopeptides.

Preparation

Preparation by reaction of acetic anhydride on phloroglucinol,
with concentrated sulfuric acid at 130° (70%)
with boron trifluoride at 10° (62.5–68%)
with zinc chloride at 145–150° (50%)
with Amberlite IR-120 or Zeokarb 225 (cation exchange resins, sulfonic acid type) at 160° (39%).

Biological Activity

monoacetylphloroglucinol (mapg), small molecular weight phenolic metabolite, is produced via bacteria including pseudomonas strains. mapg is acetylated to form the broad-spectrum antibiotic, 2,4-diacetylphloroglucinol (dapg) by mapg acetyltransferase. in addition, mapg exerts fairly weak potency when exhibiting a broad range of antibiotic activity. even though weakly active, it seems that mapg is essential in the biocontrol of plant diseases by some pseudomonas strains [1].

Purification Methods

Crystallise the ketone from hot H2O (35mL/g). [Beilstein 8 IV 2729.]

References

[1]. hayashi, a., saitou, h., mori, t., matano, i., sugisaki, h., & maruyama, k. molecular and catalytic properties of monoacetylphloroglucinol acetyltransferase frompseudomonassp. ygj3. bioscience, biotechnology, and biochemistry. 2012; 76(3): 559-566.