Dibenzylideneacetone

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.

The Uses of Dibenzylideneacetone

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, 1980
The Journal of Organic Chemistry, 45, p. 3840, 1980 DOI: 10.1021/jo01307a022
Organic Syntheses, Coll. Vol. 2, p. 167, 1943

Biological Activity

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].

Purification Methods

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

References

[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.