Avobenzone

Toxicity

A minimum toxic dose has not been established. Significant toxicity is not expected

Background

Avobenzone is dibenzoyl methane derivative. It is oil soluble ingredient. Avobenzone has the ability to absorb ultraviolet light over wider range of wavelengths. It is included in many commercially available sunscreens which are used as wide spectrum sunscreens. Avobenzone is very sensitive to light, to increase its stability and duration of action, photostablizers are added in the sunscreen product. Avobenzone has an absorption maximum of 357 nm. Sunscreens containing avobenzone is indicated for providing protection from the sun. In addition to limiting the skin's exposure to the sun, using sunscreen agents may help reduce long-term sun damage such as premature aging of the skin and skin cancer.

Indications

Sun protection factor, added in the sunscreen products for its wide spectrum ultraviolet absorption properties.

Definition

ChEBI: Avobenzone is a member of dihydrochalcones.

General Description

Avobenzone is a dibenzoylmethane derivative for which the ground state is a mixture of the enol/ keto forms. Only the enol form is an effective UVA absorber. When irradiated with UVA light, it generates a triplet excited state in the keto form that can cause the avobenzone to degrade, as well as cause deep-level skin damage. Avobenzone can lose up to 36% of its potential for UV absorption after only 1 hour of exposure to sunlight, if not stabilized.

Synthesis

Avobenzone is produced synthetically by reacting 4-tert-butylbenzoic methyl ester (from 4-tert-butylbenzoic acid by esterification with methanol) with 4-methoxyacetophenone in toluene in the presence of sodium amide.