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

Description

2'-HYDROXY-6'-METHOXYACETOPHENONE is a yellow crystalline powder that serves as an essential intermediate in the synthesis of various compounds with potential applications in the pharmaceutical industry. It is a key component in the production of aminopyrazole compounds, 5,7,4'-disubstituted flavones, naphthopyrazolyl carbothioamides, and other bioactive molecules.

Uses

Used in Pharmaceutical Industry:
2'-HYDROXY-6'-METHOXYACETOPHENONE is used as a starting material for the synthesis of aminopyrazole compounds, which are employed as anticancer agents and Chk1 inhibitors. These compounds have shown potential in treating cancer by targeting specific cellular pathways and inhibiting the growth of cancer cells.
Used in Synthesis of 5,7,4'-Disubstituted Flavones:
2'-HYDROXY-6'-METHOXYACETOPHENONE is used as a precursor in the preparation of 5,7,4'-disubstituted flavones, which are predicted to act as androgen receptor antagonists. These compounds have potential applications in the treatment of androgen-dependent conditions and diseases.
Used in Synthesis of Anticancer Agents:
2'-HYDROXY-6'-METHOXYACETOPHENONE is also utilized in the synthesis of naphthopyrazolyl carbothioamides, which are known to possess anticancer properties. These agents target specific cellular mechanisms, contributing to the development of novel cancer therapies.
Used in Synthesis of Flavones:
2'-HYDROXY-6'-METHOXYACETOPHENONE has been used as a starting material in the synthesis of 5-methoxyflavaone and 5,6-dihydroxyflavone. These flavones are known for their diverse biological activities, including antioxidant, anti-inflammatory, and anticancer properties.

Preparation

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

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 
• 127-19-5 N,N-dimethyl acetamide 
• 217813-03-1 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate 
• 1352515-27-5 2-hydroxy-6-methoxy-a-methylbenzenemethanol 
• 150-19-6 O-methylresorcine 
• 75-77-4 chloro-trimethyl-silane 
• 85630-30-4 N,N-diethyl-2-hydroxy-6-methoxybenzamide 
• 67-56-1 methanol 
• 4056-73-9 2-acetyl-1,3-cyclohexanedione 

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.

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Chromones and xanthones are oxygen-containing heterocyclic compounds acknowledged by their antioxidant properties. In an effort to develop novel agents with improved activity, a series of compounds belonging to these chemical classes were prepared. Their syntheses involve the condensation of appropriate 2-methyl-4H-chromen-4-ones, obtained via Baker-Venkataraman rearrangement, with (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde to provide the corresponding 2-[(1E,3E)-4-(3,4-dimethoxyphenyl)buta-1,3-dien-1-yl]-4H-chromen-4-ones. Subsequent electrocyclization and oxidation of these compounds led to the synthesis of 1-aryl-9H-xanthen-9-ones. After cleavage of the protecting groups, hydroxylated chromones and xanthones were assessed as scavenging agents against both reactive oxygen species (ROS) [superoxide radical (O2?-), hydrogen peroxide (H2O2), hypochlorous acid (HOCl), singlet oxygen (1O2), and peroxyl radical (ROO?)] and reactive nitrogen species (RNS) [nitric oxide (?NO) and peroxynitrite anion (ONOO-)]. Generally, all the tested new hydroxylated chromones and xanthones exhibited scavenger effects dependent on the concentration, with IC50 values found in the micromolar range. Some of them were shown to have improved scavenging activity when compared with previously reported analogues, allowing the inference of preliminary conclusions on the structure-activity relationship.