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

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

Downstream Products

• 54987-77-8 3.4.4'.6'-tetramethoxy-2'-acetoxy-trans-chalcone 
• 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 
• 93012-86-3 7-methoxy-3',4',5-trihydroxyflavanone 
• 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.].

Anti‐melanogenic properties of velutin and its analogs?

Velutin, one of the flavones contained in natural plants, has various beneficial activities, such as skin whitening, as well as anti‐inflammatory, anti‐allergic, antioxidant, and antimicrobial activities. However, the relationship between the structure of velutin and its anti‐melanogenesis activity is not yet investigated. In this study, we obtained 12 velutin derivatives substituted at C5, C7, C3′, and C4′ of the flavone backbone with hydrogen, hydroxyl, and methoxy functionalities by chemical synthesis, to perform SAR analysis of velutin structural analogues. The SAR study revealed that the substitution of functional groups at C5, C7, C3′, and C4′ of the flavone backbone affects biological activities related to melanin synthesis. The coexistence of hydroxyl and methoxy at the C5 and C7 position is essential for inhibiting tyrosinase activity. However, 1,2‐diol compounds substituted at C3′ and C4′ of flavone backbone induce apoptosis of melanoma cells. Further, substitution at C3′ and C4′ with methoxy or hydrogen is essential for inhibiting melanogenesis. Thus, this study would be helpful for the development of natural‐derived functional materials to regulate melanin synthesis.

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.