Dibenzylideneacetone Struktur

1,5-Diphenylpenta-1,4-dien-3-on

Bezeichnung:1,5-Diphenylpenta-1,4-dien-3-on

CAS-Nr538-58-9

Englisch Name:Dibenzylideneacetone

CBNumberCB3705221

SummenformelC17H14O

Molgewicht234.29

MOL-Datei538-58-9.mol

Synonyma

1,5-Diphenylpenta-1,4-dien-3-on

1,5-Diphenylpenta-1,4-dien-3-on physikalisch-chemischer Eigenschaften

Schmelzpunkt	107-113 °C
Siedepunkt	336.62°C (rough estimate)
Dichte	1.0477 (rough estimate)
Brechungsindex	1.5000 (estimate)
storage temp.	Sealed in dry,Room Temperature
Aggregatzustand	solid
Farbe	yellow
Stabilität	Stable. Incompatible with strong oxidizing agents. Combustible.
InChIKey	WMKGGPCROCCUDY-UHFFFAOYSA-N
CAS Datenbank	538-58-9(CAS DataBase Reference)
EPA chemische Informationen	1,4-Pentadien-3-one, 1,5-diphenyl- (538-58-9)

Sicherheit

S-Sätze:	22-24/25
WGK Germany	3
HS Code	2914790090

Gefahreninformationscode (GHS)

Dibenzylideneacetone Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
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.
Verwenden
Dibenzylideneacetone is used as a ligand to prepare palladium catalysts, which are widely used in catalytic hydrogenation, coupling, carbonylation, alkyne ring trimerization, etc.
synthetische
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, 1980
The Journal of Organic Chemistry, 45, p. 3840, 1980 DOI: 10.1021/jo01307a022
Organic Syntheses, Coll. Vol. 2, p. 167, 1943
Biologische Aktivität
Dibenzylideneacetone (DBA) showed inhibitory activity against Botrytis cinerea Chitinase with an IC50 of 13.10 μg/mL. The MIC of DBA against B. cinerea was 32 μg/mL, and the EC50 values for inhibition of hyphae growth and spore germination were 16.29 and 14.64 μg/mL, respectively. DBA was able to significantly extend the shelf life of cherry tomato shelf life and is a promising antifungal agent for fruit preservation^[1].
läuterung methode
Crystallise the ketone from hot ethyl acetate (2.5mL/g) or EtOH. [Beilstein 7 IV 1747.]
Einzelnachweise
[1] XIAODI NIU; Chenyang W; Ziyou Wang, HONGSU WANG*. Dibenzylideneacetone Overcomes Botrytis cinerea Infection in Cherry Tomatoes by Inhibiting Chitinase Activity[J]. Journal of Agricultural and Food Chemistry, 2023. DOI:10.1021/acs.jafc.3c05695.

Dibenzylideneacetone Upstream-Materialien And Downstream Produkte

1,5-Diphenylpenta-1,4-dien-3-on Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

538-58-9, Dibenzylideneacetone Verwandte Suche:

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