90-24-4

Basic information

• Product Name: 2'-HYDROXY-4',6'-DIMETHOXYACETOPHENONE
• Synonyms: 6-HYDROXY-2,4-DIMETHOXYACETOPHENONE;4',6'-DIMETHOXY-2'-HYDROXYACETOPHENONE;4,6-DIMETHOXY-2-HYDROXYACETOPHENONE;1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)ETHAN-1-ONE;1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)ETHANONE;2'-HYDROXY-4',6'-DIMETHOXYACETOPHENONE;2-HYDROXY-4,6-DIMETHOXYACETOPHENONE;2,4-DIMETHOXY-6-HYDROXYACETOPHENONE
• CAS NO: 90-24-4
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.2
• EINECS: 201-978-3
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);C10;Carbonyl Compounds;Ketones;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Inhibitors
• Mol File: 90-24-4.mol
• Article Data: 132

Chemical Properties

• Melting Point: 80-84 °C(lit.)
• Boiling Point: 185°C/20mm
• Flash Point: 185°C/20mm
• Appearance: /
• Density: 1.172g/cm³
• Vapor Pressure: 1.57E-05mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Soluble in hot methanol.
• PKA: 9.41±0.15(Predicted)
• Merck: 14,10067
• BRN: 1285013
• CAS DataBase Reference: 2'-HYDROXY-4',6'-DIMETHOXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-HYDROXY-4',6'-DIMETHOXYACETOPHENONE(90-24-4)
• EPA Substance Registry System: 2'-HYDROXY-4',6'-DIMETHOXYACETOPHENONE(90-24-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 90-24-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 90-24-4 differently. You can refer to the following data:
1. 1-(2-Hydroxy-4,6-dimethylphenyl)-ethanone was investigated for its properties as an antibacterial agent and urease inhibitory effects.
2. 2'-Hydroxy-4',6'-dimethoxyacetophenone is a chemical with potential antibacterial agent effects and urease inhibitory effects as well as synthesis applications.

Preparation

Preparation by reaction of acetonitrile on phloroglucinol dimethyl ether (Hoesch reaction).

InChI:InChI=1/C10H12O4/c1-6(11)10-8(12)4-7(13-2)5-9(10)14-3/h4-5,12H,1-3H3

Upstream product

• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 7446-70-0 aluminium trichloride 
• 60-29-7 diethyl ether 
• 10034-85-2 hydrogen iodide 
• 108-24-7 acetic anhydride 
• 7647-01-0 hydrogenchloride 
• 500-99-2 3,5-dimethoxyphenol 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 75-05-8 acetonitrile 
• 67-64-1 acetone 
• 71-43-2 benzene 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 125553-65-3 4',6'-dimethoxy-2'-(4-nitrobenzoyloxy)acetophenone 
• 105476-00-4 1-(2-ethoxy-4,6-dimethoxy-phenyl)-ethanone 
• 19158-99-7 (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 59263-72-8 2-hydroxy-4,6-dimethoxyacetophenone monoacetate 
• 855839-06-4 1,1′-(2-hydroxy-4,6-dimethoxy-1,3-phenylene)bis(ethan-1-one) 
• 53350-27-9 (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 
• 1775-97-9 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropenone 
• 1775-97-9 flavokawain B 
• 1036-72-2 5,7-dimethoxyflavone 
• 33495-30-6 2-benzoyloxy-4,6-dimethoxyacetophenone 
• 108979-34-6 (2E)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)-3-(3-chlorophenyl)-2-propen-1-one 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 110048-31-2 5,7-dimethoxy-2-(2-methoxymethoxy-phenyl)-chroman-4-one 
• 2555-38-6 4-hydroxy-5,7-dimethoxycoumarin 

Relevant articles and documents

Total Synthesis and Cytotoxic Activity of 6,8-Dimethoxy-1,3-dimethylisoquinoline Isolated from Ancistrocladus tectorius: A 6π-Azaelectrocyclization Approach

A facile and convenient approach toward the total synthesis of 1,3-dimethyl-6,8-dimethoxyisoquinoline from phloroacetophenone is reported. The sequence entailed the selective 2,4-di-O-methylation and further triflation of the resulting phenolic product. This was followed by a Stille-type allylation, an allyl-to-propenyl isomerization, and the methoximation of the carbonyl moiety. A final microwave-assisted 6π-azaelectrocyclization completed the sequence. Functionalized derivatives on C-1 were also prepared. The heterocycles exhibited cytotoxic activity.

Construction and Biological Evaluation of Small Libraries Based on the Intermediates within the Total Synthesis of Uvaretin

-

Identification of novel androgen receptor degrading agents to treat advanced prostate cancer

Prostate cancer (PCa) is one of the most common malignancies affecting men worldwide. Androgen receptor (AR) has been a target of PCa treatment for nearly six decades. AR antagonists/degraders can effectively treat PCa caused by increased AR overexpression. However, all approved AR antagonists have similar chemical structures and exhibit the same mode of action on the protein. Although initially effective, resistance to these AR antagonists usually develops. Therefore, this calls for the identification of novel chemical structures of AR antagonists to overcome the resistance. Herein, we employed the synergetic combination of virtual and experimental screening to identify a flavonoid compound which not only effectively inhibits AR transcriptional activity, but also induces the degradation of the protein. Based on this compound, we designed and synthesized a series of derivatives. We discovered that the most potent compound 10e could effectively inhibit AR transcriptional activity, and possessed a profound ability to cause degradation of both full length- and ARv7 truncated forms of human AR. Notably, 10e efficiently inhibited the growth of ARv7 dependent prostate cancer cell-lines, which are completely resistant to all current anti-androgens. Compound 10e also showed strong antitumor activity in the LNCaP (androgen dependent prostate cancer cell line) in vivo xenograft model. These results provide a foundation for the development of a new class of AR antagonists.