ChemicalBook CAS DataBase List 538-58-9

538-58-9

Name	DIBENZYLIDENEACETONE
CAS	538-58-9
EINECS(EC#)	208-697-5
Molecular Formula	C17H14O
MDL Number	MFCD00004790
Molecular Weight	234.29
MOL File	538-58-9.mol

Synonyms

1,5-DIPHENYL-1,4-PENTADIEN-3-ONE 1,5-DIPHENYL-3-PENTADIENONE 1,5-DIPHENYL-PENTA-1,4-DIEN-3-ONE AKOS 213-33 DBA DIBENZAL ACETONE DIBENZYLIDENEACETONE DISTYRYL KETONE TRANS,TRANS-1,5-DIPHENYL-1,4-PENTADIEN-3-ONE TRANS,TRANS-1,5-DIPHENYLPENTA-1,4-DIEN-3-ONE TRANS,TRANS-DIBENZALACETONE TRANS,TRANS-DIBENZYLIDENEACETONE TRANS,TRANS-DISTYRYL KETONE (1E,4E)-1,5-Diphenyl-1,4-pentadien-3-one 1,4-Pentadien-3-one, 1,5-diphenyl- 1,5-Diphenyl-1,4-pentadiene-3-one 1,5-diphenyl-4-pentadien-3-one Bis(2-phenylvinyl) ketone Styrol ketone 1,5-Diphenyl-3-Pentadieneone

Chemical Properties

Appearance	yellow powder
Melting point	107-113 °C
Boiling point	336.62°C (rough estimate)
density	1.0477 (rough estimate)
refractive index	1.5000 (estimate)
storage temp.	0-6°C
form	solid
color	yellow
Stability:	Stable. Incompatible with strong oxidizing agents. Combustible.
InChI	InChI=1S/C17H14O/c18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16/h1-14H
InChIKey	WMKGGPCROCCUDY-UHFFFAOYSA-N
SMILES	C(C1=CC=CC=C1)=CC(=O)C=CC1=CC=CC=C1
CAS DataBase Reference	538-58-9(CAS DataBase Reference)
EPA Substance Registry System	1,4-Pentadien-3-one, 1,5-diphenyl- (538-58-9)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H315-H317-H319-H335-H413
Precautionary statements	P261-P280-P305+P351+P338
Safety Statements	S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . less more
WGK Germany	3
TSCA	TSCA listed
HS Code	2914790090

Hazard Information

Chemical Properties

yellow powder

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, 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.

Spectrum Detail

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