3006. Dibenzalacetone

Nomenclature

CAS number: 538-58-9
1,5-Diphenyl-1,4-pentadien-3-one; dibenzylidene acetone; distyryl ketone.
C17H14O; mol wt 234.29.
C 87.15%, H 6.02%, O 6.83%.

Description and references

Prepn from benzaldehyde + acetone: Conrad, Dolliver, Org. Synth. 12, 22 (1939); Haslam, US 2719863 (1955 to du Pont); Tokár et al., Acta Chim. Acad. Sci. Hung. 19, 83 (1959). Prepn of geometrical isomers: Dinwiddie et al., J. Org. Chem. 27, 327 (1962).

Chemical structure

Derivative

(E,E)-Form.

Nomenclature

CAS number: 35225-79-7

Properties

Crystals from hot ethyl acetate, mp 110-111°. uv max: 330 nm (ε 34,300). Practically insol in water. Slightly sol in alc, ether; sol in acetone, chloroform.

Derivative

(1Z,4E)-Form.

Nomenclature

CAS number: 115587-57-0

Properties

Light yellow needles from ethanol, mp 60°. uv max: 295 nm (ε 20,000).

Derivative

(Z,Z)-Form.

Nomenclature

CAS number: 58321-78-1

Properties

Yellow oil, bp0.02 130°. uv max: 287 nm (ε 11,000).

Use

In sun protection preparations.