703-23-1

Basic information

• Product Name: 2'-HYDROXY-6'-METHOXYACETOPHENONE
• Synonyms: 6'-Hydroxy-2'-methoxyacetophenone;Acetophenone, 2'-hydroxy-6'-methoxy-;2'-HYDROXY-6'-METHOXYACETOPHENONE;2-HYDROXY-6-METHOXYACETOPHENONE;1-(2-HYDROXY-6-METHOXYPHENYL)ETHAN-1-ONE;1-(2-HYDROXY-6-METHOXYPHENYL)ETHANONE;2-Acetyl-3-methoxyphenol;2'-Hydroxy-6'-methoxyacetophenone,97%
• CAS NO: 703-23-1
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 211-872-9
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Benzene series;C9;Carbonyl Compounds;Ketones
• Mol File: 703-23-1.mol
• Article Data: 35

Chemical Properties

• Melting Point: 58-60 °C(lit.)
• Boiling Point: 141 °C16 mm Hg(lit.)
• Flash Point: 141°C/16mm
• Appearance: Yellow crystalline powder
• Density: 1.158
• Vapor Pressure: 0.00798mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.79±0.10(Predicted)
• BRN: 1869049
• CAS DataBase Reference: 2'-HYDROXY-6'-METHOXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-HYDROXY-6'-METHOXYACETOPHENONE(703-23-1)
• EPA Substance Registry System: 2'-HYDROXY-6'-METHOXYACETOPHENONE(703-23-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: N
• Hazardous Substances Data: 703-23-1(Hazardous Substances Data)

Usage

Chemical Properties

Yellow crystalline powder

Uses

Different sources of media describe the Uses of 703-23-1 differently. You can refer to the following data:
1. 2''-Hydroxy-6''-methoxyacetophenone is useful in the synthesis of an aminopyrazole compound which is used to treat cancer and inhibits Chk1. 2''-Hydroxy-6''-methoxyacetophenone is also used to prepare 5,?4''-?disubstituted flavones, predicted androgen receptor antagonists and naphthopyrazolyl carbothioamides which are anticancer agents.
2. 2′-Hydroxy-6′-methoxyacetophenone was used as starting material in the synthesis of 5-methoxyflavaone. It was also used in synthesis of 5,6-dihydroxyflavone.

Preparation

Preparation by reaction of methyl iodide on 2,6-dihydroxyacetophenone with potassium carbonate in boiling acetone (56%).

General Description

An organometallic synthetic route to 2′-hydroxy-6′-methoxyacetophenone was reported.

InChI:InChI=1/C9H10O3/c1-6(10)9-7(11)4-3-5-8(9)12-2/h3-5,11H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 699-83-2 2,6-dihydroxylacetophenone 
• 2040-04-2 2,6-dimethoxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 211449-28-4 Diethyl-carbamic acid 2-acetyl-3-methoxy-phenyl ester 
• 5451-83-2 acetic acid 3-methoxyphenyl ester 
• 85630-17-7 3-methoxyphenyl N,N-diethylcarbamate 
• 2555-29-5 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one 
• 67-56-1 methanol 
• 37514-00-4 2-acetyl-1,3-cyclohexanedione enol 
• 127-19-5 N,N-dimethyl acetamide 
• 217813-03-1 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate 
• 74-83-9 methyl bromide 

Downstream Products

• 3839-98-3 2'-ethoxy-6'-methoxyacetophenone 
• 111391-33-4 4-benzyloxy-2'-hydroxy-6'-methoxy-trans-chalcone 
• 412022-08-3 3-acetyl-2-hydroxy-4-methoxy-benzaldehyde 
• 109469-61-6 2'-hydroxy-6'-methoxy-2-methoxymethoxy-trans-chalcone 
• 110048-25-4 2'-hydroxy-3,6'-dimethoxy-2-methoxymethoxy-trans-chalcone 
• 103440-57-9 1-(2-hydroxy-3-iodo-6-methoxy-phenyl)-ethanone 
• 33539-20-7 6-methoxy-2,5-dihydroxyacetophenone 
• 38226-01-6 1-(2-hydroxy-6-methoxy-3-nitro-phenyl)-ethanone 
• 37113-62-5 1-(3-bromo-2-hydroxy-6-methoxy-phenyl)-ethanone 
• 3147-64-6 2-hydroxy-6-methoxybenzoic acid 
• 98954-40-6 2-ethyl-3-methoxyphenol 
• 109341-92-6 1-(2-hydroxy-3,5-diiodo-6-methoxy-phenyl)-ethanone 
• 109589-33-5 (E)-1-(2-hydroxy-6-methoxyphenyl)-3-(3,4-methylenedioxy-phenyl)prop-2-en-1-one 
• 103154-01-4 bis-(3-acetyl-2-hydroxy-4-methoxy-phenyl)-sulfide 

Relevant articles and documents

Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors

The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC50 of 72 ± 2 nM and its 8-C-glucoside orientin with an IC50 of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 ? resolution and quambalarine B at 2.5 ? resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.

With 5, 2 '- dihydroxy - 4' - methoxy - 3 - geranyl flavone skeleton derivative and its preparation and use

The invention discloses a derivative with a 5,2'-dihydroxy-4'-methoxy-3-geranylated flavone framework and a preparation method for the derivative and use of the derivative. The derivative is represented by the chemical general formula (I) or is pharmaceutically acceptable salts thereof: the formula (I) is shown in the description, wherein R1 represents -OCH3 or -OH, R2 is -Cl or -Br, R3 is -OCH3 or -OH, and R4 is -OCH3 or -OH. The obtained derivative has good cervical cancer resisting activity, has multiple target points, multiple links and multiple effects, is low in toxicity and is not easy to cause drug resistance.

The synthesis and synergistic antifungal effects of chalcones against drug resistant Candida albicans

To identify effective and low toxicity synergistic antifungal compounds, 24 derivatives of chalcone were synthesized to restore the effectiveness of fluconazole against fluconazole-resistant Candida albicans. The minimal inhibitory concentration (MIC80) and the fractional inhibitory concentration index (FICI) of the antifungal synergist fluconazole were measured against fluconazole-resistant Candida albicans. This was done via methods established by the clinical and laboratory standards institute (CLSI). Of the synthesized compounds, 2′-hydroxy-4′-methoxychalcone (8) exhibited the most potent in vitro (FICI = 0.007) effects. The structure activity relationship of the compounds are then discussed.