Octocrylene
Also known as: 2-Ethylhexyl 2-cyano-3,3-diphenylacrylate, 2-Ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate
Description
Octocrylene is a cyanoacrylate-based UV absorber that provides protection across the UVB and short UVA range (290–360 nm), with peak absorption around 303 nm. Approved by the FDA at up to 10%, it serves a dual role in sunscreen formulations: as a direct UV absorber and, critically, as a photostabilizer for avobenzone. Octocrylene quenches the excited triplet state of avobenzone, preventing its photodegradation and maintaining broad-spectrum UVA protection. It has a favorable safety profile, though concerns have been raised about its degradation product benzophenone, a potential endocrine disruptor and photoallergen, which may accumulate in aged formulations. [Burnett 2011]
Mechanism of Action
Octocrylene absorbs UV radiation through its 2-cyano-3,3-diphenylacrylate chromophore, dissipating absorbed energy as heat via vibrational relaxation. As a photostabilizer, it acts as a triplet-state quencher for avobenzone — it accepts energy from the excited triplet state of avobenzone's diketo form via triplet–triplet energy transfer, preventing the irreversible photolysis that would otherwise destroy avobenzone's UVA-absorbing capacity. Octocrylene itself is highly photostable due to the rigidity of its acrylate backbone, making it an ideal stabilizing partner in broad-spectrum formulations. [Shaath 2010]
Indications
Available Concentrations
Side Effects
Contraindications
- Known hypersensitivity to octocrylene or acrylate compounds
- History of photoallergic contact dermatitis to octocrylene
Pregnancy Category
Not formally classified (topical use generally considered low risk)
Found In
Cosmetics containing Octocrylene
Related Conditions
References
- Burnett ME, Wang SQ. "Current sunscreen controversies: a critical review." Photodermatol Photoimmunol Photomed, 2011. doi:10.1111/j.1600-0781.2011.00557.x
- Matta MK, Zusterzeel R, Pilli NR, et al. "Effect of sunscreen application under maximal use conditions on plasma concentration of sunscreen active ingredients." JAMA, 2019. doi:10.1001/jama.2019.5586
- Shaath NA. "Ultraviolet filters." Photochem Photobiol Sci, 2010. doi:10.1039/b9pp00174c
Limitations
This page provides a general overview of Octocrylene in dermatology. It does not cover every possible use, formulation, or interaction. Individual responses to compounds vary — what works for one person may not work for another. Always consult a qualified dermatologist before starting or changing any treatment.