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538-58-9

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538-58-9 Usage

Chemical Properties

trans,trans-Dibenzylideneacetone is a crystalline solid, melting point 110-111℃; cis-trans is a light yellow needle crystal, melting point 60℃; cis-cis is a yellow oily liquid, boiling point 130℃ (2.7Pa). Soluble in ethanol, acetone, chloroform, insoluble in water.

Uses

Dibenzylideneacetone is used as a ligand to prepare palladium catalysts, which are widely used in catalytic hydrogenation, coupling, carbonylation, alkyne ring trimerization, etc.

Preparation

Dibenzylideneacetone is obtained by the reaction of benzaldehyde and acetone. The reaction was carried out in aqueous ethanol solution at a reaction temperature of 20-25°C with a yield of 78%.

Synthesis Reference(s)

Chemistry Letters, 9, p. 51, 1980The Journal of Organic Chemistry, 45, p. 3840, 1980 DOI: 10.1021/jo01307a022Organic Syntheses, Coll. Vol. 2, p. 167, 1943

Purification Methods

Crystallise the ketone from hot ethyl acetate (2.5mL/g) or EtOH. [Beilstein 7 IV 1747.]

Check Digit Verification of cas no

The CAS Registry Mumber 538-58-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 8 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 538-58:
(5*5)+(4*3)+(3*8)+(2*5)+(1*8)=79
79 % 10 = 9
So 538-58-9 is a valid CAS Registry Number.
InChI:InChI=1/C17H14O/c18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16/h1-14H/b13-11+,14-12u

538-58-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,5-Diphenyl-3-pentadienone

1.2 Other means of identification

Product number -
Other names Styrol ketone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:538-58-9 SDS

538-58-9Relevant articles and documents

Preparation and characterization of a synthetic curcumin analog inclusion complex and preliminary evaluation of in vitro antileishmanial activity

Adeoye, Oluwatomide,Cabral-Marques, Helena,Carvalheiro, Manuela Colla,Francisco, Ana Paula,Pinto, Luciana Matos Alves,Thomasi, Sérgio Scherrer

, (2020)

The aim of this work was to prepare and characterize inclusion complexes between a synthetic curcumin analog (dibenzalacetone, DBA) and beta-cyclodextrin (β-CD); and to evaluate their in vitro antileishmanial activity. DBA was synthetized and characterized by spectroscopic methods and the inclusion complexes were obtained by kneading and lyophilization (LIO) in 1:1 and 1:2 stoichiometries. Phase solubility and dissolution assays showed a 40-fold increase in the aqueous solubility of DBA and its complete dissolution from LIO 1:1 formulation after 120 min respectively. Solid-state characterization by differential scanning calorimetry and near infrared spectroscopy demonstrated the inclusion of DBA in the β-CD cavity at the molar ratios tested, with LIO 1:1 formulation being the most stable. Using nuclear magnetic resonance experiments, the protons inside the cavity of β-CD were the most affected after the inclusion of DBA molecule. The cellular viability of THP-1 macrophage cells treated with plain DBA, β-CD and DBA/CD inclusion complexes showed that the plain DBA and DBA/CD at 1:2 stoichiometry presented toxicity, while β-CD alone and DBA/CD at 1:1 stoichiometry showed no toxicity up to 640 μg mL?1. The in vitro assay with free-living promastigotes demonstrated that plain DBA and β-CD had IC50 of 320 μg mL?1 respectively, while only inclusion complexes with 1:1 stoichiometry showed antiproliferative activity with IC50 = 51.3 μg mL?1. Using the amastigote intracellular forms, there was also a difference between the plain and β-CD complexed DBA with complexes of 1:1 and 1:2 stoichiometry presenting EC50 = 66.3 μg mL?1 and 58.9 μg mL?1 respectively. The study concluded that DBA/CD at 1:1 molar ratio has the potential to decrease the intrinsic toxicity of plain DBA towards Leishmania host cells, which may be a therapeutic advantage in the application of these compounds.

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Kiseleva et al.

, (1975)

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Spectral investigation and structural characterization of Dibenzalacetone: β-Cyclodextrin inclusion complex

Periasamy,Rajamohan,Kothainayaki,Sivakumar

, p. 155 - 163 (2014)

The interaction of Dibenzalacetone (DBA) with β-Cyclodextrin (β-CD) producing an inclusion complex was carried out by co-precipitation method. The binding constant was determined using steady state and time-resolved fluorescence spectroscopy and the results suggested that the inclusion complex preferred 1:1 stoichiometry. The complex was characterized by UV-Visible, infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC) and X-ray diffractometry (XRD). The morphological characteristics of the solid complex were analyzed by Scanning electron microscope (SEM) and Atomic force microscope (AFM). The structure of 1:1 inclusion complex of DBA with β-CD is proposed. The Docking study reveals that this structure was found to be highly probable and energitically favorable model.

Synthesis of lithium/cesium-Zagronas from zagrosian natural asphalt and study of their activity as novel, green, heterogeneous and homogeneous nanocatalysts in the Claisen–Schmidt and Knoevenagel condensations

Soleiman-Beigi, Mohammad,Ghalavand, Saba,Venovel, Hadis Gholami,Kohzadi, Homa

, p. 3267 - 3279 (2021/06/17)

A novel, heterogeneous and homogeneous basic nanocatalysts were synthesized by grafting of lithium and cesium on zagrosian natural asphalt sulfonate (Li/Cs-Zagronas). The activity of these catalysts was examined in the Claisen–Schmidt and Knoevenagel condensations under mild reaction conditions. Li/Cs-Zagronas were characterized by FT-IR spectroscopy, scanning electron microscopy, X-ray diffraction, energy-dispersive spectroscopy, inductively coupled plasma and thermogravimetric analysis techniques. These nanocatalysts were removed by simple filtration and reused several times without any deterioration of activity.

Heterogeneous acid catalyzed synthesis and spectroscopic characterization of schiff bases derived from chalcone derivatives

Ajani, Olayinka O.,Jolayemi, Emmanuel G.,Owolabi, Fisayo E.,Tolu-Bolaji, Olayinka O.,Audu, Oluwatosin Y.

, p. 193 - 200 (2021/01/18)

Schiff bases have continued to gain attention as essential building blocks and versatile pharmacophores in drug development and drug-like molecular entities. Thus, the synthesis of Schiff bases was achieved herein via facile acetic acid catalyzed synthetic transformation of chalcones. The targeted Schiff bases and related compounds 2a-m were accessed by the treatment of amines with chalcone 1 which was previously derived through Claisen-Schmidt reaction between benzaldehyde and acetone, at ambient temperature. Structural characterization was achieved via physicochemical properties and the use of IR, UV, 1H and 13C NMR which were spectroscopic techniques. The compounds have essential candidature for further study, in biological activity so as to unleash their medicinal potential.

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