114021-60-2

Basic information

• Product Name: 2'-HYDROXY-3,4,4',6'-TETRAMETHOXYCHALCONE
• Synonyms: 2'-HYDROXY-3,4,4',6'-TETRAMETHOXYCHALCONE;3-(3,4-DIMETHOXYPHENYL)-1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-2-PROPEN-1-ONE
• CAS NO: 114021-60-2
• Molecular Formula: C19H20O6
• Molecular Weight: 344.36
• Mol File: 114021-60-2.mol
• Article Data: 30

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2'-HYDROXY-3,4,4',6'-TETRAMETHOXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-HYDROXY-3,4,4',6'-TETRAMETHOXYCHALCONE(114021-60-2)
• EPA Substance Registry System: 2'-HYDROXY-3,4,4',6'-TETRAMETHOXYCHALCONE(114021-60-2)

Safety Data

• Hazardous Substances Data: 114021-60-2(Hazardous Substances Data)

Upstream product

• 77-78-1 dimethyl sulfate 
• 520-33-2 hesperetin 
• 108-73-6 3,5-dihydroxyphenol 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 76650-20-9 1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone 
• 871878-99-8 1-(2,4-dimethoxyphenyl)-2-hydroxyethanone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 500-99-2 3,5-dimethoxyphenol 
• 39856-08-1 3,4-dimethoxy-cinnamoyl chloride 

Downstream Products

• 17060-20-7 2,3-dihydro-5,7-dimethoxy-2-(4'-dimethoxyphenyl)-4H-1-benzopyran-4-one 
• 95931-33-2 Bis(3,4,4',6'-tetramethoxy-2'-chalconoxy)methane 
• 95931-32-1 2,5-Dihydro-6,8-dimethoxy-3-(3',4'-dimethoxyphenyl)-1-benzoxepin 
• 23053-69-2 (Z)-2-(3,4-dimethoxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one 
• 1244-78-6 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone 

Relevant articles and documents

Synthesis and antiproliferative activity of aminoalkylated chalcones on three human cancer cells

Abstract: Two series of 16 novel aminoalkylated chalcone derivatives 2a–h and 3a–h were synthesized from 2′-hydroxy-3,4,4′,6′-tetramethoxychalcone (1) through extending alkoxy side chain at the 2′-position, and introducting amine hydrogen bond receptor at the end of the side chain. Their in vitro antiproliferative activities were evaluated on a panel of three human cell lines (Hela, HCC1954, and SK-OV-3) by CCK-8 assay. The results showed that all the target compounds, except compound 3e, exhibited moderate to potent antiproliferative activities against these three human cancer cells with the IC50 values of 6.78–64.45 μmol/L, in particular compounds 2g (on Hela cells), 2c (on HCC1954 cells), and 2c, 2d (on SK-OV-3 cells) possess IC50 values below 10 μmol/L. It showed the introduction of aminoalkyl moiety at 2′-O-position of chalcone 1 resulted to produce the desired effect of increasing the antiproliferative activities, and the distance between the amino groups and chalcone moiety plays an important role, the optimal number of methylene units is two-carbon spacer. Graphical abstract: A series of 16 novel aminoalkylated chalcones were synthesized and their antiproliferative acivities on three human cancer cells were evaluated. [InlineMediaObject not available: see fulltext.].

Identification of methoxylchalcones produced in response to CuCl2 treatment and pathogen infection in barley

Changes in specialized metabolites were analyzed in barley (Hordeum vulgare) leaves treated with CuCl2 solution as an elicitor. LC-MS analysis of the CuCl2-treated leaves showed the induced accumulation of three compounds. Among them

Attrition-enhanced deracemization and absolute asymmetric synthesis of flavanones from prochiral precursors

Seven racemic 5,7-dimethoxyflavanones afforded conglomerate crystals upon recrystallization from a solvent. Three methodologies were investigated to achieve asymmetric transformation based on dynamic crystallization of the chiral conglomerate system. The first was chiral symmetry breaking of racemic flavanones by attrition-enhanced deracemization. Continuous suspension of racemic flavanones in a small amount of propanol in the presence of a base (1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)) and glass beads promoted chiral symmetry breaking and converted the flavanones to crystals of (+)- or (-)-enantiomers with 78 to 99% ee. The second method involved cyclization of the intermediate aldol product to give optically active flavanone with 90% ee involving a reversible oxa-Michael addition reaction with attrition-enhanced deracemization. The third was a reaction starting from prochiral 2-hydroxy-4,6-dimethoxyacetophenone and 2-naphthaldehyde under basic conditions, which gave the corresponding flavanone in 89% ee.