3420-72-2

Basic information

• Product Name: 2'-HYDROXY-4,4',6'-TRIMETHOXYCHALCONE
• Synonyms: 1-(2-Hydroxy-4,6-diMethoxyphenyl)-3-(4-Methoxyphenyl)prop-2-en-1-one;FLAVOKAWAIN A;FLAVOKAWIN A;(E)-1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-3-(4-METHOXYPHENYL)PROP-2-EN-1-ONE;1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-3-(4-METHOXYPHENYL)-2-PROPEN-1-ONE;2'-HYDROXY-4,4',6'-TRIMETHOXYCHALCONE;2'-Hydroxy-4,4',6'-trimethoxy;4-Methoxybenzylidene(4,6-dimethoxy-2-hydroxyacetophenone)
• CAS NO: 3420-72-2
• Molecular Formula: C₁₈H₁₈O₅
• Molecular Weight: 314.33
• Product Categories: Chemical Synthesis;Organic Building Blocks;Chalcones;Plant Oils, Toxins, Phenolic Acids & Derivatives;C15 to C38;Carbonyl Compounds;Ketones;Building Blocks;C15 to C38;Carbonyl Compounds
• Mol File: 3420-72-2.mol
• Article Data: 54

Chemical Properties

• Melting Point: 112-116 °C(lit.)
• Boiling Point: 529.9°Cat760mmHg
• Flash Point: 193.2°C
• Appearance: /
• Density: 1.207g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 6.78±0.40(Predicted)
• CAS DataBase Reference: 2'-HYDROXY-4,4',6'-TRIMETHOXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-HYDROXY-4,4',6'-TRIMETHOXYCHALCONE(3420-72-2)
• EPA Substance Registry System: 2'-HYDROXY-4,4',6'-TRIMETHOXYCHALCONE(3420-72-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 3420-72-2(Hazardous Substances Data)

Usage

Uses

2′-Hydroxy-4,4′,6′-trimethoxychalcone may be used to synthesize 2′,2”′-dihydroxy-4,4′,4′′,4”′,6′,6′′′-hexamethoxy[5′,5′′′]bichalcone and 3′-bromo-4,4′,6′-trimethoxy-2′-hydroxychalcone.

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 62014-87-3 helichrysetin 
• 74-88-4 methyl iodide 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 77-78-1 dimethyl sulfate 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 67-56-1 methanol 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 108-73-6 3,5-dihydroxyphenol 
• 871878-99-8 1-(2,4-dimethoxyphenyl)-2-hydroxyethanone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 480-66-0 2,4,6-trihydroxyacetophenone 

Downstream Products

• 95931-35-4 (E)-1-(2-{3,5-Dimethoxy-2-[(E)-3-(4-methoxy-phenyl)-acryloyl]-phenoxymethoxy}-4,6-dimethoxy-phenyl)-3-(4-methoxy-phenyl)-propenone 
• 66074-95-1 4',5,7-trimethoxyflavanone 
• 95931-34-3 2,5-Dihydro-6,8-dimethoxy-3-(4'-methoxyphenyl)-1-benzoxepin 
• 95931-35-4 Bis(4,4',6'-trimethoxy-2'-chalconoxy)methane 
• 111570-58-2 6-ethoxycarbonyl-3-(2'-hydroxy-4,6'-dimethoxyphenyl)-5(4''-methoxyphenyl)cyclohex-2-en-1-one 
• 10493-04-6 2-(4'-methoxybenzylidene)-4,6-dimethoxycoumaran-3-one 
• 1098-92-6 kaempferol 5,7,4'-trimethyl ether 
• 5128-44-9 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 1162-82-9 4',5,7-trimethoxyisoflavone 
• 35095-45-5 8-bromo-5,7-dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one 
• 51254-82-1 2'-acetoxy-4,4',6'-trimethoxychalcone 
• 822-16-2 sodium stearate 
• 67859-06-7 5,7-dimethoxy-2-(4-methoxyphenyl)-2H-chromene 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 

Relevant articles and documents

Practical synthesis of naringenin

Two routes for the synthesis of the flavanone naringenin are described. In the first, 3,5-dimethoxyphenol is converted to 2-hydroxy- 4,6-dimethoxyacetophenone and then by condensation with anisaldehyde to 2′-hydroxy-4,4′,6′-trimethoxychalcone. The chalcone is then cyclised with aqueous hydrochloric acid and demethylated with pyridine hydrochloride to form naringenin in 45% overall yield. The condensation of 2-hydroxy-4,6-dimethoxyacetophenone with anisaldehyde could also directly produce 4′,5,7-trimethoxyflavanone, which was then converted into naringenin in 60% overall yield. In the second route, a single step for the preparation of the chalcone is used in which 1,3,5-trimethoxybenzene is acylated with p-methoxycinnamic acid. Although the synthesis of naringenin is achieved in a lower overall yield of 29%, the process is simpler.

An improved synthesis of apigenin

Two routes for the synthesis of the flavone apigenin are described. In the first, taxicatigenin was converted to 2-hydroxy-4,6- dimethoxyacetophenone and then by condensation with anisaldehyde to 2′-hydroxy-4,4′,6′-trimethoxychalcone. The latter was cyclised with iodine and demethylated with pyridine hydrochloride to form apigenin in 53% overall yield. In the second route, a single step for the preparation of the chalcone was used in which 1,3,5-trimethoxybenzene was acylated with p-methoxycinnamic acid. Although the synthesis of apigenin was achieved in a lower overall yield of 34%, the process was simpler.

Flavokawain a induces apoptosis in MCF-7 and MDA-MB231 and inhibits the metastatic process in vitro

Introduction: The kava-kava plant (Piper methsyticum) is traditionally known as the pacific elixir by the pacific islanders for its role in a wide range of biological activities. The extract of the roots of this plant contains a variety of interesting mol

Design, synthesis and biological evaluation of dimethyl cardamonin (DMC) derivatives as P-glycoprotein-mediated multidrug resistance reversal agents

Background: P-glycoprotein (P-gp) has been regarded as an important factor in the multidrug resistance (MDR) of tumor cells within the last decade, which can be solved by inhibiting P-gp to reverse MDR. Thus, it is an effective strategy to develop inhibitor of P-gp. Objective: In this study, the synthesis of a series of derivatives had been carried out by bioisosterism design on the basis of Dimethyl Cardamonin (DMC). Subsequently, we evaluated their reversal activities as potential P-glycoprotein (P-gp)-mediated Multidrug Resistance (MDR) agents. Methods: Dimethyl cardamonin derivatives were synthesized from acetophenones and the corresponding benzaldehydes in the presence of 40% KOH by Claisen-Schmidt reaction. Their cytotoxicity and reversal activities in vitro were assessed with MTT. Moreover, the compound B4 was evaluated by Doxorubicin (DOX) accumulation, Western blot and wound-healing assays deeply. Results and Discussion: The results showed that compounds B2, B4 and B6 had the potency of MDR reversers with little intrinsic cytotoxicity. Meanwhile, these compounds also demonstrated the capability to inhibit MCF-7 and MCF-7/DOX cells migration. Besides, the most compound B4 was selected for further study, which promoted the accumulation of DOX in MCF-7/DOX cells and inhibited the expressionof P-gp at protein levels. Conclusion: The above findings may provide new insights for the research and development of P-gp-mediated MDR reversal agents.

Synthesis method of isolicoflavonol

The invention provides a synthesis method of isolicoflavonol, which comprises the following steps: carrying out condensation reaction on 2,4-O-R1(protective group, the same below)-6-hydroxyacetophenone and 4-O-R2(protective group, the same below)-benzaldehyde to generate 2',4'-O-R1-6'-hydroxy-4-O-R2-chalcone; oxidizing the chalcone to generate flavonol; carrying out selective protection on 3-OH ofthe flavonol to obtain 3,5,7-O-R1-4'-O-R2-flavonol; removing the protecting group R2 from the 3,5,7-O-R1-4'-O-R2-flavonol to obtain 3,5,7-O-R1-4'-hydroxyflavonol; carrying out 1,1-dimethylpropargyl reaction on the 4,4'-OH site to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonol; carrying out partial hydrogenation on the alkynyl of the 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonolunder the action of a catalyst to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol and carrying out Claisen rearrangement on the 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol to obtain 3,5,7-O-R1-isolicoflavonol, and removing the protecting group R1 from the 3,5,7-O-R1-isolicoflavonol to obtain the isolicoflavonol.