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

Description

2,4,6-Trihydroxy phenyl benzyl ketone, also known as 2-Phenyl-2′,4′,6′-trihydroxyacetophenone, is an organic compound with a unique structure that features a benzyl ketone core and three hydroxyl groups attached to the phenyl ring. 2,4,6-TRIHYDROXY PHENYL BENZYL KETONE has the potential for various applications in different industries due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
2,4,6-Trihydroxy phenyl benzyl ketone is used as a chemical intermediate for the synthesis of pharmaceutical compounds. It can undergo reaction with citral to give the corresponding polycycle containing a citran and cyclol nucleus, which may possess biological and pharmaceutical properties. This makes it a valuable component in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,4,6-Trihydroxy phenyl benzyl ketone serves as a versatile building block for the creation of various organic compounds. Its unique structure allows it to participate in a wide range of chemical reactions, making it a useful tool for chemists and researchers in the development of new materials and compounds.
Used in Research and Development:
2,4,6-Trihydroxy phenyl benzyl ketone is also used in research and development settings to study its properties and potential applications. Its reactivity and structural features make it an interesting subject for scientific investigation, which could lead to the discovery of new uses and applications in various industries.

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 
• 28750-78-9 4,6-Dihydroxy-2-phenyl-cumaran-3-on 
• 103-82-2 phenylacetic acid 
• 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 
• 15485-75-3 5,7-dihydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid ethyl ester 
• 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 
• 4044-00-2 5,7-dihydroxyisoflavone 
• 65490-07-5 1-(2-Hydroxy-4,6-bis-methoxymethoxy-phenyl)-2-phenyl-ethanone 

Relevant articles and documents

Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease

Despite the rapidly increasing number of patients suffering from type 2 diabetes, Alzheimer's disease, and diabetes-induced dementia, there are no disease-modifying therapies that are able to prevent or block disease progress. In this work, we investigate the potential of nature-inspired glucosylpolyphenols against relevant targets, including islet amyloid polypeptide, glucosidases, and cholinesterases. Moreover, with the premise of Fyn kinase as a paradigm-shifting target in Alzheimer's drug discovery, we explore glucosylpolyphenols as blockers of Aβ-induced Fyn kinase activation while looking into downstream effects leading to Tau hyperphosphorylation. Several compounds inhibit Aβ-induced Fyn kinase activation and decrease pTau levels at 10 μM concentration, particularly the per-O-methylated glucosylacetophloroglucinol and the 4-glucosylcatechol dibenzoate, the latter inhibiting also butyrylcholinesterase and β-glucosidase. Both compounds are nontoxic with ideal pharmacokinetic properties for further development. This work ultimately highlights the multitarget nature, fine structural tuning capacity, and valuable therapeutic significance of glucosylpolyphenols in the context of these metabolic and neurodegenerative disorders.

Synthesis, Characterization, and Antioxidant Activities of Genistein, Biochanin A, and Their Analogues

A series of naturally occurring genistein (3) and biochanin A (4) compounds and their analogues were synthesized from phloroglucinol. The structures of all the synthesized compounds were established by the combined use of 1HNMR, 13CNMR, IR spectral data, and mass spectrometry; their antioxidant activities were investigated. Most of the synthesized compounds show moderate-to-high activity; only two compounds exhibit no significant activity.

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.