The most widely used UVA absorber in broad-spectrum sunscreens is 4-tert-butyl-4
-methoxydibenzoylmethane
(avobenzone). However, the photostability of avobenzone is solvent-dependent. The
aim of this work was to investigate the photostability of avobenzone in solvents of different polarity
and proticity. Four solvents were employed, namely, cyclohexane, ethyl acetate, dimethylsulfoxide and
methanol. The cause of the instability of avobenzone in these solvents was determined by means of
UV spectroscopy, high performance liquid chromatography, gas chromatography–mass spectrometry and
nuclear magnetic resonance spectroscopy. The effect of oxygen on the photo-instability was also determined.
Avobenzone was found to lose absorption efficacy as a result of photoisomerisation from the
enol to the keto form and/or photodegradation to form photoproducts that absorb principally in the UVC
region, depending on the solvent. It was found to be essentially photostable in the polar protic solvent
methanol but photoisomerised in the polar aprotic solvent dimethylsulfoxide. In the nonpolar solvent
cyclohexane, it photodegraded appreciably. Both photoisomerisation and photodegradation occurred to
a similar extent in the moderately polar aprotic solvent ethyl acetate. Photoisomerisation occurred only
in the presence of oxygen whereas photodegradation occurred irrespective of oxygen. This knowledge is
important in order to achieve the correct formulation for sunscreens incorporating avobenzone.