I’ve received quite a few questions about the organic sunscreen chemical Avobenzone over the years and I wanted to shed some light on one of the most common concerns – its photodegradation in UV. These concerns are usually raised by websites that say things like, “Avobenzone degrades in the sun, resulting in the release of free radicals that may actually increase the risk for cancer.”
What these quotes often leave out is the context, which is important in understanding why Avobenzone is so commonly used in sunscreens and why it is effective.
Avobenzone or butyl methoxydibenzoyl methane is an organic sunscreen that absorbs in the UVA region and has global approval. Among the sunscreen chemicals available in the US it is the strongest and most effective UVA absorber. Avobenzone exists in two chemical forms when in solution, the enol form and the diketo (or keto) form.
When exposed to UV light some Avobenzone in the enol form can be changed into the keto form – however this is slowly reversed once Avobenzone is removed from UV light.
In its keto form Avobenzone is susceptible to photodegradation from UV light. The energy from UV light causes structural changes in the Avobenzone that can lead to breakdown products. In many cases, those breakdown products no longer effectively absorb UVA and UVB (some of them will absorb UVC). Some of these breakdown products are also thought to be irritants. The other concern is that some singlet oxygen can also be formed – a reactive oxygen species which can damage DNA and cells.
The above only relates to Avobenzone on its own though, the material that Avobenzone is dissolved into and other chemicals in the formula can change how easily Avobenzone photodegrades. Other modifications like encapsulating Avobenzone have also been tested, though the benefit is often reduced contact between Avobenzone and the skin – not photostability.
Photostabilizers generally work by absorbing energy from the Avobenzone before it becomes unstable and breaks and down. Effective photostabilizers will then be able to take this energy and dissipate it in safer forms, most often heat.
A company that produces Avobenzone, DSM Nutritional Products, performed a study testing different photostabilizers and their effect on Avobenzone’s phostability. The most commonly used and known photostabilizer of Avobenzone is the organic sunscreen chemical Octocrylene, but there are other photostabilizers that don’t act as sunscreens such as Polyester-8 and Polysilicone-15.
To perform the test, 4% Avobenzone and different photostabilizers were dissolved into a mixture of 70% ethanol, 15% caprylic/capric triglyceride, and 15% C12-15 alkyl benzoate. The solutions were placed on glass slides at a density of 2 mg/cm2 then exposed to 25 MED (Minimal Erythemal Dose, 1 MED defined by the US FDA as 200 Joules/Meter2) units of UV light. After exposure, the amount of Avobenzone remaining was determined.
What the researchers found was that the combination of 4% Avobenzone and 3-5% Octocrylene maintained 90% of the Avobenzone after 25 MEDs of UV light. Based on this, they tested different combinations of Octocrylene and other photostabilizers to see how well they stabilized Avobenzone.
They found that 3.6% Octocrylene with 4% Bis Ethylhexyloxyphenyl Methoxyphenol Triazine or 4% 4-Methylbenzylidene Camphor were able to completely stabilize the Avobenzone after 25 MED of UV.
There’s currently no global standard on photostability, different regions have their own standards. In the US as part of the Broad Spectrum test, sunscreens are pre-irradiated with 4 MED before testing.
Just like how some chemicals can increase the photostability of Avobenzone, others like Octinoxate (Octyl Methoxycinnamate) are known to speed up the photodegradation of Avobenzone. This paper is often misquoted to include Oxybenzone (2-Hydroxy-4-Methoxybenzophenone), often mischaracterized as not photostable, as a chemical that increases the photodegradation of Avobenzone, but it was included as an internal standard to allow comparison between samples – as it did not photodegrade in the experiment.
What matters when it comes to the protection offered by a sunscreen are the values and ratings determined from standardized tests like SPF, PPD, Broad Spectrum, etc and not the appearance of an ingredient on the INCI.
Basing assumptions on INCI is dangerous, as the only way to truly know is to test the products. An experiment on 6 different commercial sunscreens on their photostability highlights this. 4/6 of the organic sunscreens tested exhibited a decrease in photoprotection after UV exposure. Of the two photostable organic sunscreens one contained a combination of Avobenzone and 4-Methylbenzylidene Camphor and the other Octocrylene, Avobenzone, Mexoryl SX, and Titanium Dioxide. The one inorganic sunscreen tested was shown to be photostable after UV exposure.
Keep in mind, this study tested commercial sunscreens available in 2006, where photostability was a relatively newer concern for sunscreens and standards had not yet been defined. It was around this time that Neutrogena began marketing its Helioplex patent, a photostable combination of Avobenzone, Diethylhexyl 2,6-Naphthalate, and Oxybenzone. The Helioplex US patent was granted in 2002 and other patents for increasing photostability of Avobenzone are present as early as 1999, when the US FDA finalized the use of Avobenzone in sunscreens.
While we still do not have a global standard for photostability, the options for and knowledge to stabilize sunscreens has grown considerably. It also still very important to reapply your sunscreen throughout UV exposure, this compensates for any protection lost through photodegradation as well as physical changes in the film of sunscreen on the skin.
Source: C. Mendrok-Edinger, K. Smith, A Janssen, J. Vollhardt. The Quest for Avobenzone Stabilizers and Sunscreen Photostability, Cosmetics and Toiletries, http://www.cosmeticsandtoiletries.com/formulating/category/suncare/premium-the-quest-for-avobenzone-stabilizers-and-sunscreen-photostability-214405251.html