2051-07-2

Basic information

• Product Name: BIS(4-METHOXYBENZYLIDENE)ACETONE
• Synonyms: (E,E)-1,5-BIS-(4-METHOXYPHENYL)-1,4-PENTADIEN-3-ON;(E,E)-1,5-BIS(4-METHOXYPHENYL)-1,4-PENTADIEN-3-ONE;DIANISYLIDENE ACETONE;DI-(4,4'-DIMETHOXY)-BENZYLIDENE-ACETONE;BIS(4-METHOXYBENZYLIDENE)ACETONE;(1E,4E)-1,5-BIS(4-METHOXYPHENYL)-1,4-PENTADIEN-3-ONE;1,5-BIS-(4-METHOXYPHENYL)-3-PENTADIENONE;1,5-DI(4-METHOXYPHENYL)PENTA-1,4-DIEN-3-ONE
• CAS NO: 2051-07-2
• Molecular Formula: C₁₉H₁₈O₃
• Molecular Weight: 294.34
• EINECS: 262-278-1
• Product Categories: Adehydes, Acetals & Ketones;Anisoles, Alkyloxy Compounds & Phenylacetates;Aromatics
• Mol File: 2051-07-2.mol
• Article Data: 77

Chemical Properties

• Melting Point: 128-129 °C
• Boiling Point: 492℃
• Flash Point: 244℃
• Appearance: /
• Density: 1.128
• Vapor Pressure: 7.88E-10mmHg at 25°C
• Refractive Index: 1.5490 (estimate)
• BRN: 1885379
• CAS DataBase Reference: BIS(4-METHOXYBENZYLIDENE)ACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(4-METHOXYBENZYLIDENE)ACETONE(2051-07-2)
• EPA Substance Registry System: BIS(4-METHOXYBENZYLIDENE)ACETONE(2051-07-2)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• RTECS: RZ2476500
• Hazardous Substances Data: 2051-07-2(Hazardous Substances Data)

Usage

Chemical Properties

light yellow crystalline powder

InChI:InChI=1/C19H18O3/c1-21-18-11-5-15(6-12-18)3-9-17(20)10-4-16-7-13-19(22-2)14-8-16/h3-14H,1-2H3/b9-3-,10-4+

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 67-64-1 acetone 
• 98272-52-7 5-acetonyl-dihydro-furan-2-one 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 2573-85-5 2,3,5,6-Tetrahydro-2,6-di-p-anisylthiopyran-4-one 1,1-dioxide 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 123-54-6 acetylacetone 
• 2573-84-4 2,3,5,6-Tetrahydro-2,6-p-anisylthiopyran-4-one 
• 3815-30-3 4-(4-methoxyphenyl)-3-buten-2-one 
• 116222-10-7 (2S,6R)-2,6-Bis-(4-methoxy-phenyl)-1-methyl-piperidin-4-one 
• 115584-10-6 r⁽²⁾,c⁽⁶⁾-bis(p-methoxyphenyl)piperidine-4-one 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 108-46-3 recorcinol 

Downstream Products

• 41167-39-9 2,6-bis-(4-methoxy-phenyl)-4-oxo-cyclohexane-1,1-dicarboxylic acid dimethyl ester 
• 75335-21-6 5,5-Dimethoxy-1,4-bis(4-methoxyphenyl)-1-penten-3-on 
• 75347-08-9 meso-2,4-Bis(4-methoxyphenyl)-1,1,5,5-tetramethoxy-3-pentanon 
• 75335-24-9 (+/-)-2,4-Bis(4-methoxyphenyl)-1,1,5,5-tetramethoxy-3-pentanon 
• 89725-78-0 2,6-Bis-(4-methoxy-phenyl)-bicyclo[5.3.1]undecane-4,11-dione 
• 74882-32-9 1,5-bis(4-methoxyphenyl)pentan-3-one 
• 150160-31-9 7,11-bis(4-methoxyphenyl)-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone 
• 181520-09-2 7,11-Bis-(4-methoxy-phenyl)-3-thioxo-2,4-diaza-spiro[5.5]undecane-1,5,9-trione 
• 137569-07-4 C₄₅H₅₀O₅ 
• 1354948-34-7 C₂₁H₂₆O₃ 
• 1354948-33-6 C₂₀H₂₄O₃ 

Relevant articles and documents

Second harmonic generation in pyrazoline derivatives of dibenzylideneacetones and chalcone: A combined experimental and theoretical approach

In this work, we investigate theoretically and experimentally second harmonic generation (SHG) in three pyrazoline compounds, being two derivatives of dibenzylideneacetone (DBA) (C23H20N2 and C25H24N2O2) and one derivative of chalcone (C21H18N2). The compounds were synthesized after two steps employing a Claisen-Schmidt condensation followed by an addition-elimination reaction with phenylhydrazine. All compounds were characterized using NMR, FT-IR, UV-Vis, and XRD. We calculated the first-order hyperpolarizabilities of these molecules using program packages based on the time-dependent Hartree-Fock (TDHF) and density functional theory (DFT). SHG was characterized by Kurtz and Perry's powder method. We observed that these organic crystals present SHG efficiencies up to 5 times larger than the KDP, and we associated these values to their molecular structure and crystalline arrangements. The values obtained experimentally and theoretically evidence that these compounds have good potential for application in electronic devices based on second-order nonlinear responses.

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The synthesized 1,5 diarylpenta-1,4-dien-3-one derivatives (compounds 1-6) as synthetic curcumin analogues were tested for their potential anticancer activity against human ovarian and lung adenocarcinoma cells. The absorption, distribution, metabolism, excretion, and toxicity (ADMET/pharmacokinetic) parameters of all the compounds were predicted by admetSAR software. The pharmacokinetics, pharmacodynamics and bioactivity scores properties based on Lipinski rule and Ghose filter, calculated with the help of Molinspiration and ChemDraw. Molecular docking evaluation of all the compounds was also performed by using AutoDock Vina and iGEMDOCK against three most common human anticancer targets; epidermal growth factor receptor (EGFR), heat shock protein (Hsp 90-α), and vascular endothelial growth factor receptor-2 (VEGFR2). The obtained results were compared with the reference compound 7 and drugs 8-10 (7: GO-035; 8: Quinazolin; 9: Naquotinib and 10: Ribofuranuronamide). Finding indicates, all the compounds were potentially interacting with VEGFR2 through the average –9.1 binding energy (BE) with closer contact 1H-NMR). In vitro anti-proliferative activity was tested via MTT method against human ovarian carcinoma (PA-1) and human lung adenocarcinoma (A549) cells and further screened for apoptotic parameters such as nuclear fragmentation and ROS generation. Compound 4 exhibits good dose-dependent anti-proliferative activity (IC50 73 and 79.7 μM) against human ovarian carcinoma and human lung adenocarcinoma, respectively. Communicated by Ramaswamy H. Sarma.