52182-14-6

Basic information

• Product Name: 3,4'-DIMETHOXYCHALCONE
• Synonyms: 3,4'-DIMETHOXYBENZYLIDENEACETOPHENONE;3,4'-DIMETHOXYCHALCONE;3-(3-methoxyphenyl)-1-(4-methoxyphenyl)-2-propen-1-on;3-(3-methoxyphenyl)-1-(4-methoxyphenyl)-2-propen-1-one;DIMETHOXYCHALCONE,3,4-(RG);DIMETHOXYFLAVONE, 3',4'-(RG);2-Propen-1-one, 3-(3-methoxyphenyl)-1-(4-methoxyphenyl)-;Brn 3140713
• CAS NO: 52182-14-6
• Molecular Formula: C₁₇H₁₆O₃
• Molecular Weight: 268.31
• Product Categories: Chalcones
• Mol File: 52182-14-6.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 435.1°C at 760 mmHg
• Flash Point: 208.8°C
• Appearance: /
• Density: 1.128g/cm³
• Vapor Pressure: 8.98E-08mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 3,4'-DIMETHOXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4'-DIMETHOXYCHALCONE(52182-14-6)
• EPA Substance Registry System: 3,4'-DIMETHOXYCHALCONE(52182-14-6)

Safety Data

• Hazardous Substances Data: 52182-14-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H16O3/c1-19-15-9-7-14(8-10-15)17(18)11-6-13-4-3-5-16(12-13)20-2/h3-12H,1-2H3/b11-6+

Upstream product

• 20912-79-2 4-methoxyphenacylidene dimethylsulphurane 
• 19350-71-1 N'-(3-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 7099-91-4 p-methoxybenzoylformic acid 
• 6099-04-3 3-methoxycinnamic acid 
• 591-31-1 3-methoxy-benzaldehyde 
• 1226526-58-4 2-(benzo[d]thiazol-2-ylsulfonyl)-1-(4-methoxyphenyl)ethanone 
• 15851-92-0 (E)-3-methoxycinnamoyl chloride 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 3654-50-0 3-(3-hydroxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one 
• 74-88-4 methyl iodide 

Downstream Products

• 1188386-75-5 3-(4-bromo-3-methoxyphenyl)-1-(4-methoxyphenyl)allylketone 
• 1092964-13-0 5-(3-methoxyphenyl)-3-(4-methoxyphenyl)-1H-pyrazole 
• 1122659-71-5 2,3-dibromo-1-(4-methoxyphenyl)-3-(3-methoxyphenyl)propane-1-one 
• 1380395-74-3 3-(3-methoxyphenyl)-1-(4-methoxyphenyl)pent-4-en-1-ol 
• 1380395-69-6 3-(3-methoxyphenyl)-1-(4-methoxyphenyl)pent-4-en-1-one 
• 63144-61-6 1-methoxy-3-(3-(4-methoxyphenyl)propyl)benzene 
• 75849-21-7 1-(4-methoxyphenyl)-3-(3-methoxyphenyl)propan-1-ol 
• 75849-31-9 7-methoxy-1-(4-methoxyphenyl)indan 
• 75849-32-0 5-methoxy-1-(4-methoxyphenyl)indan 
• 75849-24-0 1-(4-methoxyphenyl)-3-(3-methoxyphenyl)prop-1-ene 
• 74973-44-7 3-(4-methoxybenzoyl)-1-(3-methoxyphenyl)propanol 
• 169803-91-2 4-(4-Methoxy-phenyl)-2-(3-methoxy-phenyl)-4-oxo-butyric acid methyl ester 
• 169803-90-1 4-(4-Methoxy-phenyl)-2-(3-methoxy-phenyl)-4-oxo-butyronitrile 
• 75849-20-6 3-(3-methoxyphenyl)-1-(4-methoxyphenyl)propan-1-one 

Relevant articles and documents

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Synthesis, characterization, molecular docking and in vitro anticancer activity of 3-(4-methoxyphenyl)-5-substituted phenyl-2-pyrazoline-1-carbothioamide

In the present study, eight numbers of new 3-(4-methoxy phenyl)-5-substituted phenyl-2-pyrazoline-1-carbothioamide (5a-h) have been synthesized from 1-(4-methoxy phenyl)-3-(substituted phenyl)-prop-2-en-1-one (3a-h) and structurally characterized by using FT-IR,1H NMR,13C NMR, Mass and Elemental analysis. The synthesized molecules were biologically eval-uated for their in vitro anticancer activity against human breast adenocar-cinoma (MCF-7), liver cancer (Hep-G2) and leukaemia cancer (K-562) cell line using Sulforhodamine B (SRB) bioassay technique. From the all synthesized compounds 5a, 5c, 5d, and 5e exhibited potent anticancer activity (GI50= 50=44.5μg/ml) and Adriamycin (ADR) (GI50= 10μg/ml) on MCF-7 cell lines. Besides this, all the synthesized compounds have exhibited moderate activity against human liver cancer (Hep-G2) and leukaemia cancer (K-562) cell lines. In addition, molecular docking studies were also explored in order to study the probable binding specificity into the active site of Epidermal Growth Factor Receptor tyrosine kinase (EGFR) (PDB ID: 1M17) using Molegro Virtual Docker Evaluation 2013 6.0.1 (MVD). Based on the molecular docking result, it was found that compound 5a exhibited the best interaction with the above target (i.e., EGFR) by interacting with specific amino acid residues such as: Thr 766, Gin 767, Thr 830, Cys 575, Ala 719 and Met 769.

Hansch’s analysis application to chalcone synthesis by Claisen–Schmidt reaction based in DFT methodology

Chalcones are bioactive compounds obtained from either natural sources or synthetic procedures and widely used due to their several biological properties. The most common experimental methodology in obtaining these compounds is Claisen–Schmidt reaction, which is a particular type of aldolic condensation. In this work, we have synthesized 23 chalcones and by density functional theory (DFT) calculation, we have studied the difference in reactivity of the several benzaldehydes and their effects on the yield of this reaction. From molecular orbital descriptors were obtained two quantitative structure–reactivity relationship (QSRR) models based on Hansch’s analysis. The results of this study showed that, for the most benzaldehydes (15 of 23 compounds), their reactivity was correlated with LUMO energy and global Electrophilicity Index (ω) values, which are determined in the first step of Claisen–Schmidt condensation mechanism (nucleophilic addition). Likewise, for the smallest group of benzaldehydes, their reactivity was related to their HOMO and ΔL???H (LUMO???HOMO) energies, which were determined in the second step of the mechanism (trans-elimination). This is the first report of a QSRR model analyzing the yield of chalcone synthesis based on DFT methodology.