23121-32-6

Basic information

• Product Name: 2-HYDROXY-4,6-DIMETHOXY-3-METHYLACETOPHENONE
• Synonyms: 2'-Hydroxy-3'-methyl-4',6'-dimethoxyacetophenone;Methylxanthoxylin;Nsc296648;1-(2-Hydroxy-4,6-dimethoxy-3-methylphenyl)-ethanone;3-Methylxanthoxylin;Methylxanthoxyline;2-HYDROXY-4,6-DIMETHOXY-3-METHYLACETOPHENONE;4',6'-DIMETHOXY-2'-HYDROXY-3-METHYLACETOPHENONE
• CAS NO: 23121-32-6
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23
• Product Categories: Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 23121-32-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 141-142℃
• Boiling Point: 362.4 °C at 760 mmHg
• Flash Point: 140.5 °C
• Appearance: /
• Density: 1.144±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 9.26E-06mmHg at 25°C
• Refractive Index: 1.525
• PKA: 9.75±0.20(Predicted)
• CAS DataBase Reference: 2-HYDROXY-4,6-DIMETHOXY-3-METHYLACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-4,6-DIMETHOXY-3-METHYLACETOPHENONE(23121-32-6)
• EPA Substance Registry System: 2-HYDROXY-4,6-DIMETHOXY-3-METHYLACETOPHENONE(23121-32-6)

Safety Data

• Hazardous Substances Data: 23121-32-6(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of acetonitrile on 3,5-dimethoxy-2-methylphenol (Hoesch reaction) (68%).

InChI:InChI=1/C11H14O4/c1-6-8(14-3)5-9(15-4)10(7(2)12)11(6)13/h5,13H,1-4H3

Upstream product

• 83459-37-4 2,4-dihydroxy-6-methoxy-3-methylacetophenone 
• 74-88-4 methyl iodide 
• 14107-97-2 2,4,6-trimethoxytoluene 
• 75-36-5 acetyl chloride 
• 487-70-7 2,4,6-trihydroxybenzaldehyde 
• 2657-28-5 2,4,6-trihydroxy-3-methyl-acetophenon 
• 77-78-1 dimethyl sulfate 
• 88-03-9 2,4,6-trihydroxytoluene 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 859176-50-4 2-acetoxy-4,6-dimethoxy-3-methyl-benzaldehyde 
• 39827-80-0 2-hydroxy-4,6-dimethoxy-3-methylbenzoic acid 
• 89877-54-3 2-Hydroxy-4,6-dimethoxy-3-methyl-benzoesaeure-methylester 
• 16024-31-0 2,4-dimethoxy-6-nitro-toluene 
• 50827-65-1 2-hydroxy-4,6-dimethoxy-3-methylbenzaldehyde 

Downstream Products

• 39701-13-8 1-(2,4,6-trimethoxy-3-methylphenyl)ethan-1-one 
• 857566-92-8 3,4-dimethoxy-benzoic acid-(2-acetyl-3,5-dimethoxy-6-methyl-phenyl ester) 
• 108062-80-2 1-(2-benzoyloxy-4,6-dimethoxy-3-methyl-phenyl)-ethanone 
• 65349-37-3 2'-Hydroxy-4',6'-dimethoxy-3'-methyl-2-phenylpropiophenon 
• 182172-56-1 1-(3,4-dimethoxy-phenyl)-3-(2-hydroxy-4,6-dimethoxy-3-methyl-phenyl)-propane-1,3-dione 
• 111033-47-7 1-(2-hydroxy-4,6-dimethoxy-3-methyl-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione 
• 39690-10-3 2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-8-methyl-chromen-4-one 
• 116194-53-7 2-(3,4-dimethoxy-phenyl)-5-hydroxy-7-methoxy-8-methyl-chromen-4-one 
• 23367-08-0 2-(3,4-dimethoxy-phenyl)-5-hydroxy-7-methoxy-6-methyl-chromen-4-one 
• 5559-28-4 5,7-dimethoxy-2-(4-methoxy-phenyl)-8-methyl-chromen-4-one 
• 14004-50-3 5-hydroxy-7,4'-dimethoxy-8-methylflavone 
• 211749-01-8 8-methylluteolin 
• 14004-48-9 5-hydroxy-7-methoxy-8-methylflavone 
• 113863-13-1 1-(2,5-bis-benzoyloxy-4,6-dimethoxy-3-methyl-phenyl)-ethanone 

Relevant articles and documents

3-site piperazinylchalcone derivative, and pharmaceutical composition and applications thereof

The present invention relates to a 3-site piperazinylchalcone derivative, which has a structure formula represented by a general formula (I) defined in the specification, wherein R is one selected from a substituted or unsubstituted phenyl group, a fused ring group and substituted or a unsubstituted heterocyclic group. The present invention further provides a pharmaceutical composition of the3-site piperazinylchalcone derivative, and applications thereof. According to the present invention, the results of the activity test based on P-gp target show that the 3-site piperazinylchalcone derivative and the pharmaceutical composition have good activity, can provide practical value in the treatment of the multidrug resistance of tumors, can solve the technical problems of difficult synthesis and high cost in the synthesis of the reversing agent used in the prior art, and is meaningful.

Concise synthesis and cellular evaluation of 3′-formyl-4′,6′-dihydroxy-2′-methoxy-5′-methylchalcone (FMC) and its analogues

3′-Formyl-4′,6′-dihydroxy-2′-methoxy-5′-methylchalcone (FMC) was a natural product isolated from Cleistocalyx operculatus. A four-step synthetic strategy toward FMC and its four analogues (1b-1e) was first developed. All compounds were synthesized from commercially available 2,4,6-trihydroxyacetophenone; formylation at 3′ position under Vilsmeier-Haack conditions was followed by the introduction of a methyl group at 5′ position. The key step of selective methylation at 2′ position was achieved by trimethylsilyldiazomethane (TMSCHN2). Then substituted aromatic aldehydes were condensed through Claisen-Schmidt reaction in the presence of potassium hydroxide. All structures were confirmed by 1H NMR, 13C NMR, and high-resolution mass spectra. FMC and analogues were screened for their antiproliferative activity.

Synthesis, cytotoxicity, and antioxidative activity of minor prenylated chalcones from Humulus lupulus

The minor hop (Humulus lupulus) chalcones 3′-geranylchalconaringenin (3), 5′-prenylxanthohuraol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1″,2″-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3′-geranyl-6′-O- methylchalconaringenin (2), 3′-methylflavokawin (6), and 2′-0-methyl-3′-prenylchalconaringenin (7) were also synthesized. Cytotoxicity was investigated in HeLa cells, and these compounds all had IC 50 values comparable to xanthohumol (8.2-19.2 μM). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.