2',4',6'-Trihydroxyacetophenone monohydrate Chemical Properties

Melting point:

219-221 °C(lit.)

Boiling point:

257.07°C (rough estimate)

Density 

1.3037 (rough estimate)

refractive index 

1.5090 (estimate)

storage temp. 

Store below +30°C.

solubility 

DMSO (Sparingly), Ethanol (Slightly), Methanol (Slightly), Water (Very Slightly,

pka

7.76±0.23(Predicted)

form 

Powder

color 

light yellow

Water Solubility 

Soluble in water.

BRN 

1911197

Stability:

Stable under recommended storage conditions., Stable Under Recommended Storage C

LogP

1.472 (est)

CAS DataBase Reference

480-66-0(CAS DataBase Reference)

NIST Chemistry Reference

Ethanone, 1-(2,4,6-trihydroxyphenyl)-(480-66-0)

EPA Substance Registry System

Ethanone, 1-(2,4,6-trihydroxyphenyl)- (480-66-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

RTECS 

AN0528000

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29145000

MSDS

• Language:English Provider:2',4',6'-Trihydroxyacetophenone monohydrate

2',4',6'-Trihydroxyacetophenone monohydrate Usage And Synthesis

Chemical Properties

Light Brown Solid

Uses

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.

Uses

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].

target

HMG-CoA Reductase

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.

2',4',6'-Trihydroxyacetophenone monohydrate(480-66-0)Related Product Information

• Acetophenone
• MELIBIOSE
• 3,5-Dihydroxyacetophenone
• 2-HYDROXYACETOPHENONE
• 2',6'-Dihydroxyacetophenone
• 3'-Hydroxyacetophenone
• 2,4-Dihydroxyacetophenone
• 4-Nitroacetophenone
• 4'-(Trifluoromethyl)acetophenone
• 3-Aminoacetophenone
• 4'-Hydroxyacetophenone
• 3,4-Dihydroxyacetophenone
• 2'-Hydroxyacetophenone
• 4'-Bromoacetophenone
• 2',4'-Dichloroacetophenone
• 3-Nitroacetophenone
• Chloral hydrate
• Rutin