727-71-9

Basic information

• Product Name: 2,4,6-TRIHYDROXY PHENYL BENZYL KETONE
• Synonyms: 1-(2,4,6-TRIHYDROXYPHENYL)-2-PHENYLETHANONE;2-PHENYL-1-(2,4,6-TRIHYDROXYPHENYL)ETHAN-1-ONE;2-PHENYL-1-(2,4,6-TRIHYDROXY-PHENYL)-ETHANONE;2-PHENYL-2',4',6'-TRIHYDROXYACETOPHENONE;2,4,6-TRIHYDROXY PHENYL BENZYL KETONE;SALOR-INT L251208-1EA;2',4',6'-Trihydroxy-2-phenylacetophenone
• CAS NO: 727-71-9
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24
• Product Categories: C13 to C14;Carbonyl Compounds;Ketones;Building Blocks;C13 to C14;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 727-71-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 161-165 °C(lit.)
• Boiling Point: 441.5 °C at 760 mmHg
• Flash Point: 234.9 °C
• Appearance: /
• Density: 1.38 g/cm³
• Vapor Pressure: 2.09E-08mmHg at 25°C
• Refractive Index: 1.674
• Solubility: soluble in Methanol
• CAS DataBase Reference: 2,4,6-TRIHYDROXY PHENYL BENZYL KETONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRIHYDROXY PHENYL BENZYL KETONE(727-71-9)
• EPA Substance Registry System: 2,4,6-TRIHYDROXY PHENYL BENZYL KETONE(727-71-9)

Safety Data

• Hazard Codes: Xi
• Statements: 41-43
• Safety Statements: 37/39
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 727-71-9(Hazardous Substances Data)

Usage

Uses

2-Phenyl-2′,4′,6′-trihydroxyacetophenone can undergo reaction with citral to give the corresponding polycycle containing a citran and cyclol nucleus, which may possess biological and pharmaceutical properties.

Preparation

Preparation by reaction of phenylacetonitrile with phloroglucinol (Hoesch reaction), ? in the presence of boron trifluoride etherate (50%).

InChI:InChI=1/C14H12O4/c15-10-7-12(17)14(13(18)8-10)11(16)6-9-4-2-1-3-5-9/h1-5,7-8,15,17-18H,6H2

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 140-29-4 phenylacetonitrile 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 28750-78-9 4,6-Dihydroxy-2-phenyl-cumaran-3-on 
• 10147-11-2 propargyl benzene 

Downstream Products

• 101446-06-4 5,7-dihydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid methyl ester 
• 143207-80-1 2,4,6-trihydroxybibenzyl 
• 34544-87-1 benzyl 2,4,6-triacetoxyphenyl ketone 
• 15485-75-3 5,7-dihydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid ethyl ester 
• 4222-02-0 4,5,7-Trihydroxy-3-phenyl-coumarin 
• 39604-66-5 2-hydroxy-4,6-dimethoxyphenyl benzyl ketone 
• 104310-95-4 3-diphenylmethyl-2,4,6-trihydroxydesoxybenzoin 
• 104310-93-2 3,5-bis(diphenylmethyl)-2,4,6-trihydroxyphenyl benzyl ketone 
• 116222-03-8 (E)-3-Phenyl-acrylic acid 4-oxo-3-phenyl-7-[(E)-(3-phenyl-acryloyl)oxy]-2-((E)-styryl)-4H-chromen-5-yl ester 
• 18651-39-3 5,7-Dihydroxy-2,3-diphenylchromone 
• 104556-47-0 α-hydroxymethylbenzyl 2-hydroxy-4,6-bisethoxymethoxyphenyl ketone 
• 28741-48-2 2,4,6-triacetoxy-bibenzyl 

Relevant articles and documents

Expedient Synthesis of Lupulones and Their Derivatization to 2,8-7H-Dihydrochromen-7-ones

A convenient and improved method for the synthesis of beta acids or lupulones, which are known to possess e. g. anti-cancer, anti-inflammatory, anti-oxidative and antimicrobial activity, has been developed successfully. Further derivatization of these complex structures to the corresponding dihydrochromen-7-ones, including the natural product machuone, was realized to simplify their analysis and to confirm their molecular structure. In addition to practical and safe laboratory procedures, the advantages associated with this new approach involve the use of water as a solvent and the direct crystallization of lupunones from acetonitrile, rendering our strategy more efficient and benign as compared to available methods.

Structural optimization and antibacterial evaluation of rhodomyrtosone B analogues against MRSA strains

Methicillin-resistant Staphylococcus aureus (MRSA) infections are well-known as a significant global health challenge. In this study, twenty-two congeners of the natural antibiotic rhodomyrtosone B (RDSB) were synthesized with the aim of specifically enhancing the structural diversity through modifying the pendant acyl moiety. The structure-activity relationship study against various MRSA strains revealed that a suitable hydrophobic acyl tail in the phloroglucinol scaffold is a prerequisite for antibacterial activity. Notably, RDSB analogue 11k was identified as a promising lead compound with significant in vitro and in vivo antibacterial activities against a panel of hospital mortality-relevant MRSA strains. Moreover, compound 11k possessed other potent advantages, including breadth of the antibacterial spectrum, rapidity of bactericidal action, and excellent membrane selectivity. The mode of action study of compound 11k at the biophysical and morphology levels disclosed that 11k exerted its MRSA bactericidal action by membrane superpolarization resulting in cell lysis and membrane disruption. Collectively, the presented results indicate that the novel modified RDSB analogue 11k warrants further exploration as a promising candidate for the treatment of MRSA infections.

Structure-activity relationships and optimization of acyclic acylphloroglucinol analogues as novel antimicrobial agents

Methicillin-resistant Staphylococcus aureus (MRSA) poses a serious threat to global public health, because it exhibits resistance to existing antibiotics and therefore high rates of morbidity and mortality. In this study, twenty-one natural product-based acylphloroglucinol congeners were synthesized, which possessed different side chains. Antibacterial screening against MRSA strains revealed that acyl moiety tailoring is a prerequisite for the antibacterial activity. Moreover, the lipophilicity, rather than the magnitude of the hydrophobic acyl tail dominates variability in activity potency. Compound 11j was identified as a promising lead for the generation of new anti-MRSA drug development. It was discovered by optimization of the side chain length in light of the potency, the breadth of the antibacterial spectrum, the rate of bactericidal action, as well as the membrane selectivity. Compound 11j exerted profound in?vitro antibacterial activity against the MRSA strain (JCSC 2172), and its MIC was 3-4 orders of magnitude lower than that of vancomycin. A preliminary mode of action study of compound 11j at the biophysical and morphology levels disclosed that the mechanism underlying its anti-MRSA activity included membrane depolarization and, to a lesser extent, membrane disruption and cell lysis.