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

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

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 
• 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 
• 15485-75-3 5,7-dihydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid ethyl ester 
• 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 
• 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.

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.

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.

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.

Synthesis and aminomethylation of 7-hydroxy-5-methoxyisoflavones

A synthetic method for 7-hydroxy-5-methoxyisoflavones starting from 5,7-dihydroxyisoflavones was developed. Dimethylcarbamoylchloride was proposed for protection of the 7-hydroxy group. Aminomethylation of the synthesized 7-hydroxy-5-methoxyisoflavones by formaldehyde aminals was studied.

Arylalkyl ketones, benzophenones, desoxybenzoins and chalcones inhibit TNF-α induced expression of ICAM-1: Structure-activity analysis

The interaction between leukocytes and the vascular endothelial cells (EC) via cellular adhesion molecules plays an important role in the pathogenesis of various inflammatory and autoimmune diseases. Small molecules that block these interactions have been targeted as potential therapeutic agents against acute and chronic inflammatory diseases. In an effort to identify potent intercellular cell adhesion molecule-1 (ICAM-1) inhibitors, a large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones and their analogs (54 in total) have been synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated the possible mechanism for their ICAM-1 inhibitory activities. The most active compound was found to be 79. A large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones as well as their analogs (54 in total) were synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated a possible mechanism of their ICAM-1 inhibitory activities. The most active compound was found to be 79. Copyright

Synthesis and structure-activity relationship study of deoxybenzoins on relaxing effects of porcine coronary artery

Deoxybenzoins are potent antioxidants and tyrosinase inhibitors with potential to be developed as food preservatives and cosmetic ingredients. To explore the potential in cardiovascular protection, 25 polyphenolic deoxybenzoins were synthesized and evaluated for inhibitory effects on KCl-induced porcine coronary arterial contraction. The results revealed deoxybenzoins are significant inhibitors of KCl-induced arterial contraction. Among those synthesized, two-thirds of the deoxybenzoins exhibited moderate to good efficacy on relaxing contracted artery including 2,4-dihydroxydeoxybenzoin with EC50 = 3.30 μM (Emax = 100%, n = 7) and 2,4-dihydroxy-4′-methoxydeoxybenzoin EC50 = 3.70 μM (E max = 100%, n = 5). Deoxybenzoins displayed an endothelium-dependent relaxing manner on the contracted artery; the contractile responses of neither endothelium denuded nor L-NAME deactivated rings were inhibited. The structure-activity relationships of deoxybenzoin on arterial relaxing effects concluded that the 2,4-dihydroxylated deoxybenzoins presented a potential vascular relaxing pharmacophore, with favoring substitution on ring B in the order of H ≤ p-OMe > p-OH > o-OMe > m,p-diOMe ≤ m-OMe.

Potential antioxidants and tyrosinase inhibitors from synthetic polyphenolic deoxybenzoins

Deoxybenzoins (DOBs) are one-pot synthetic precursors of isoflavones with feature analogous to those beneficial polyphenols such as resveratrol (stilbene) and phloretin (dihydrochalcone). In this study, seventeen polyphenolic DOBs were synthesized and evaluated by various antioxidant assays and tyrosinase inhibitory effect in vitro. Results displayed that these DOBs are powerful antioxidants; for example, 2,3,4-trihydroxy-3′,4′-dimethoxydeoxybenzoin possesses an excellent anti-lipid peroxidation activity (IC50 = 0.72 ± 0.16 μM), whilst 2,4,4′,5-tetrahydroxydeoxybenzoin showed good DPPH radical scavenging activity (IC50 = 0.69 ± 0.04 μM), which were better than Trolox and vitamin C. Besides exhibiting a weak metal chelating effect, these DOBs were effective in scavenging ABTS{radical dot}+ and superoxide anion (O2{radical dot} -) radicals. DOBs also exhibited potent mushroom tyrosinase inhibitory activity; for example 2,3,4′-trihydroxy-4-methoxydeoxybenzoin displayed stable and significant inhibitory effect on tyrosinase activity, with IC50 values 43.37, 43.10 and 46.10 μM at incubation intervals of 0.5, 1.5, and 2.5 h, respectively. These results suggest that, with the advantage of being readily synthesizable small molecules, DOBs can be potentially developed into clinical and industrial antioxidants. Crown Copyright

6-Acyl-4-aryl/alkyl-5,7-dihydroxycoumarins as anti-inflammatory agents

A series of coumarin derivatives were synthesized in two steps from phloroglucinol. The anti-inflammatory activities of these derivatives were evaluated by means of inhibiting NO production in LPS-induced RAW 264.7 cells. Derivatives 3, 8, 10, 11, and 13 exhibited low micromolar levels of anti-inflammatory activities, and these derivatives also protected DNA against hydroxyl radical attack. Coumarin derivative 8 was the most potent derivative among those tested herein against NO production in LPS-induced RAW 264.7 cells with an IC50 value of 7.6 μM, and it effectively reduced the hydroxyl radical production by 50% at 100 μM in the electron spin resonance study.