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

• 500-99-2 3,5-dimethoxyphenol 
• 621-23-8 1,2,3-trimethoxybenzene 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 94103-36-3 (2E)-1-(2,4,6-trimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 77-78-1 dimethyl sulfate 
• 871878-99-8 1-(2,4-dimethoxyphenyl)-2-hydroxyethanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 67-56-1 methanol 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 108-73-6 3,5-dihydroxyphenol 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

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 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 5631-70-9 4',5,7-trimethoxyflavone 
• 3791-75-1 2'-hydroxy-4,4',6'-trimethoxydihydrochalcone 
• 82517-06-4 3-iodo-5,7,4'-trimethoxyflavone 
• 57290-97-8 2',2'''-dihydroxy-4,4',4'',4''',6',6'''-hexamethoxy<5',5'''>bichalcone 
• 1607-73-4 (2E)-1-(2'-hydroxy-3'-bromo-4',6'-dimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one 
• 5128-44-9 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 10493-04-6 (2Z)-4,6-dimethoxy-2-(4-methoxybenzylidene)-1-benzofuran-3(2H)-one 
• 1162-82-9 4',5,7-trimethoxyisoflavone 
• 2798-20-1 gardenin B 

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

Development of a novel nitric oxide (NO) production inhibitor with potential therapeutic effect on chronic inflammation

Inflammation is a complex biological response to stimuli. Activated macrophages induced excessively release of pro-inflammatory cytokines and mediators such as endogenous radical nitric oxide (NO) play a significant role in the progression of multiple inflammatory diseases. Both natural and synthetic chalcones possess a wide range of bioactivities. In this work, thirty-nine chalcones and three related compounds, including several novel ones, based on bioactive kava chalcones were designed, synthesized and their inhibitory effects on NO production in RAW 264.7 cells were evaluated. The novel compound (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3-methoxy-4-(3-morpholinopropoxy)phenyl)prop-2-en-1-one (53) exhibited a better inhibitory activity (84.0%) on NO production at 10 μM (IC50 = 6.4 μM) with the lowest cytotoxicity (IC50 > 80 μM) among the tested compounds. Besides, western blot analysis indicated that compound 53 was a potent down-regulator of inducible nitric oxide synthase (iNOS) protein. Docking study revealed that compound 53 also can dock into the active site of iNOS. Furthermore, at the dose of 10 mg/kg/day, compound 53 could both significantly suppress the progression of inflammation on collagen-induced arthritis (CIA) and adjuvant-induced arthritis (AIA) models. In addition, the structure-activity relationship (SAR) of the kava chalcones based analogs was also depicted.

Novel chromenone derivatives having substituted biphenyl group and a pharmaceutical composition for prevention or treatment of allergic diseases compring the same

The present invention relates to: a novel chromenone derivative compound capable of effectively suppressing an allergic immune response by inhibiting signal transduction mediated by thymic stromal lymphopoietin (TSLP); and a pharmaceutical composition capable of fundamentally preventing or treating various allergic diseases by using the same.COPYRIGHT KIPO 2021