Octocrylene

Octocrylene is a very popular sunscreen ingredient that absorbs UVB and near-UVA wavelengths. It is often used to photostabilize other UV filters, especially avobenzone.

Effects


Grade Level of Evidence
A Multiple double-blind, controlled clinical trials.
B 1 double-blind, controlled clinical trial.
C At least 1 controlled or comparative clinical trial.
D Uncontrolled, observational, animal or in-vitro studies only.
Grade Effect Size of Effect Comments

D

Photoprotection

Moderate

Absorbs UVB and near-UVA wavelengths. Its SPF is proportional to its concentration in the range between 0-10%.

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Scientific Research


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Table of contents:

1. Sources

Octocrylene is an oil-soluble sunscreen that absorbs in the UVB and near-UVA regions. First introduced in sun care and cosmetic products in the late 1990s,[1] it has become increasingly popular over the years because of its ability to photostabilize the UVA filter avobenzone.[2] A 2009 survey of topical sunscreen products in the United States found that 36% contained both avobenzone and octocrylene, up from 10% in 2003 and none in 1997.[3]

In Switzerland, an investigation of 116 personal care products revealed that octocrylene was the third most popular UV filter, present in 43% of the products.[4] A larger study in Germany that analyzed 4,477 cosmetic products found avobenzone to be present in 30.7% of the products, behind only octinoxate (38.5%), titanium dioxide (40.1%) and avobenzone (48.7%).[5]

Octocrylene has also been detected in tap water samples from Spain, up to a concentration of 170 ng/L.[6]

2. Skin penetration

Sunscreen agents should ideally penetrate only into the shallow layers of the skin so that the risk of adverse systemic reactions is minimized.[7] Studies on human skin indicate that octocrylene can penetrate into the stratum corneum and the epidermis, but either cannot penetrate through the epidermis,[8][9] or permits only a minuscule amount through the epidermis into the dermis.[10] However, the total absorbed dose of octocrylene is increased in irradiated skin, though the reason for this is not clear.[11]

Nanoencapsulation of octocrylene using the polymer poly(epsilon-caprolactone) (PCL) can increase its retention in the skin, thereby avoiding systemic absorption.[12]

3. Effects on the skin

3.1 Photoprotection

The UV absorption profile of octocrylene spans from 290 to 360 nm, covering the UVB and short UVA wavelengths.[13] Its peak absorption has been variously reported to be at 303,[14] 304[15] or 307 nm.[2][13]

Octocrylene's sun protection factor (SPF) is directly proportional to its concentration, at least in the range between 0-10%. When compared against 17 other UV filters authorized in the EU by using the highest concentration allowed by European legislation for each filter, octocrylene was among the most efficacious, ahead of oxybenzone, octisalate and homosalate.[15]

Octocrylene's photoprotection can be augmented by encapsulating it within solid nanoparticles, which act as physical sunscreens on their own and can provide a synergistic UV-blocking effect.[16][17] Rice bran and raspberry seed oil-based lipid nanocarriers formulated into creams containing 3.5% of the UV filters avobenzone and octocrylene also led to improved photoprotection, reflecting up to 91% of UVA and 93% of UVB rays.[18]

3.2 Prevention of photoaging

One study has evaluated whether the photoprotection afforded by a daily use cream containing octocrylene, avobenzone and Mexoryl SX can inhibit damage to the skin induced by daily exposure to UV radiation. The buttock skin of 12 volunteers was exposed 5 days per week for 6 weeks to one minimal erythema dose of solar simulated radiation per exposure, and both treated and untreated skin were assessed for erythema, pigmentation, skin hydration, skin microtopography, histology and immunochemistry, and collagen and metalloproteinase mRNA levels. The unprotected skin sites saw melanization as well as changes in skin hydration and microtopography. The thickness of the stratum corneum and stratum granulosum was increased, and in the dermis the expression of the extracellular matrix glycoprotein tenascin was enhanced, whereas the expression of type I pro-collagen was reduced. Moreover, types I and III collagen mRNA were also slightly increased, and there was a 2.8-fold enhancement of the mRNA level of matrix metalloproteinase-2 (MMP-2). These changes were all prevented by the daily use cream, indicating that daily photoprotection with octocrylene, avobenzone and ecamsule can significantly inhibit UV-induced skin damage.[19]

3.3 Other effects and uses

Apart from its photoprotective effect, octocrylene also has anti-inflammatory properties. When a preparation containing 10% octocrylene (the highest concentration allowed in Europe) was subjected to the phorbol-myristate-acetate test using mice, 83% edema inhibition was observed. The effect was dose-dependent -- 0.5% octocrylene caused no inhibition, while at concentrations of 1.25%, 2.5% and 5% inhibitions of more than 20%, 50% and 70% were seen, respectively.[20]

A sunscreen containing octocrylene, ecamsule, avobenzone and titanium dioxide has been found to be effective in preventing the development of UV-induced skin lesions in patients with photosensitive lupus erythematosus.[21]

4. Stability

In a comparison with 17 other UV filters authorized in the European Union, octocrylene was not among the most photostable,[22] but it is believed to be an efficient singlet quencher, which may account for why it can photostabilize a number of other sunscreen actives such as avobenzone, octinoxate and oxybenzone.[23][24][25][26][27]

A formulation containing octocrylene, octinoxate and oxybenzone has even been shown to enhance the photostability of retinyl palmitate.[28]

The photostability of octocrylene can be further improved by 6 to 8-fold upon forming inclusion complexes with hydroxypropyl-beta-cyclodextrin (HP-beta-CD) in lotion formulations.[29]

5. Safety

Octocrylene is an approved sunscreen ingredient in both the United States and Europe, where it can be included up to a concentration of 10%.[30][31] Its safety profile is considered excellent overall, with low irritation, phototoxicity, and photoallergic potential.[32] It was also not subchronically toxic, developmentally toxic or genotoxic in animals, supporting its use as a human photoprotectant.[33]

However, some researchers have recommended that octocrylene should be avoided in sunscreens for children and pregnant mothers, due to its propensity to cause contact dermatitis in the former and the fact that a significant correlation exists between the use of products containing octocrylene and its presence in human breast milk.[34][35]

5.1 Enhanced production of reactive oxygen species

The absorption of octocrylene increases under irradiation.[11] Unfortunately, this increases the chance of an enhancement in the level of reactive oxygen species (ROS) in the skin, which has been demonstrated to occur when octocrylene penetrates into the epidermis.[36] The presence of antioxidants in the formulation can help prevent the damage caused by these ROS by deactivating free radicals.[27]

5.2 Photocontact and contact allergy

Octocrylene is both a photocontact allergen and a contact allergen.[37][1] Although allergic reactions to UV filters are uncommon,[38][39] studies in Europe have reported increasing numbers of patients with photocontact allergy to octocrylene since 2003.[1] In fact, there is evidence that octocrylene is now among the organic UV absorbers that most frequently elicit photoallergic contact dermatitis in Europe.[40][41]

Similarly, there are many reports of photocontact or contact allergy to octocrylene in the literature.[42][43][44][45] Octocrylene appears to be a strong contact allergen in children,[46][47][48][49] which has led some researchers to suggest that it should probably be avoided in sunscreens for this age group.[34]

Octocrylene's allergenic potency may be attributable to its photoinduced reactivity towards primary amines and alcohols,[50] causing it to react with peptides or free amino acids of the human skin.[37][51] In addition, it is known that many adult patients with photocontact allergy to octocrylene have previously used topical products containing ketoprofen,[37][46][52] leading to the suggestion that photosensitization to ketoprofen leads to photocontact allergy to octocrylene.[1]

5.3 Potential endocrine disruptor

Octocrylene has been shown to stimulate the proliferation of human breast cancer cells in vitro through what appears to be an estrogen receptor-mediated process.[53] A more recent study found that it did not upregulate endocrine-related genes in an aquatic inverterbrate at any of the tested concentrations however.[54]

5.4 No enhancement of pesticide absorption

Some sunscreen formulations have been demonstrated to enhance the dermal penetration of herbicides and pesticides.[55][56] Additional studies revealed that certain sunscreen agents such as Padimate O, octinoxate, homosalate and octisalate can increase the total penetration of the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D) to varying degrees. Octocrylene, however, had no effect or even slowed the lag time for the penetration of 2,4-D in two separate studies.[57][58]

Scientific References


  1. de Groot AC, Roberts DW. Contact and photocontact allergy to octocrylene: a review. Contact Dermatitis. (2014)
  2. Alldredge BK, et. al. Section 8: Dermatologic Disorders. Koda-Kimble and Young's Applied Therapeutics: The Clinical Use of Drugs. (2013)
  3. Wang SQ, et. al. The evolution of sunscreen products in the United States--a 12-year cross sectional study. Photochem Photobiol Sci. (2013)
  4. Manová E, et. al. Organic UV filters in personal care products in Switzerland: a survey of occurrence and concentrations. Int J Hyg Environ Health. (2013)
  5. Uter W, et. al. Coupled exposure to ingredients of cosmetic products: III. Ultraviolet filters. Contact Dermatitis. (2014)
  6. Díaz-Cruz MS, et. al. Analysis of UV filters in tap water and other clean waters in Spain. Anal Bioanal Chem. (2012)
  7. Montenegro L, Paolino D, Puglisi G. Effects of silicone emulsifiers on in vitro skin permeation of sunscreens from cosmetic emulsions. J Cosmet Sci. (2004)
  8. Jiang R, et. al. Absorption of sunscreens across human skin: an evaluation of commercial products for children and adults. Br J Clin Pharmacol. (1999)
  9. Hayden CG, et. al. Sunscreen penetration of human skin and related keratinocyte toxicity after topical application. Skin Pharmacol Physiol. (2005)
  10. Potard G, et. al. Quantitative HPLC analysis of sunscreens and caffeine during in vitro percutaneous penetration studies. Int J Pharm. (1999)
  11. Duracher L, et. al. Irradiation of skin and contrasting effects on absorption of hydrophilic and lipophilic compounds. Photochem Photobiol. (2009)
  12. do Nascimento DF, et. al. Characterization and evaluation of poly(epsilon-caprolactone) nanoparticles containing 2-ethylhexyl-p-methoxycinnamate, octocrylene, and benzophenone-3 in anti-solar preparations. J Nanosci Nanotechnol. (2012)
  13. Rai R, Shanmuga SC, Srinivas CR. Update on Photoprotection. Indian J Dermatol. (2012)
  14. Ho TTY. Factors affecting the clinical efficacy of sunscreens. Hong Kong J Dermatol Venereol. (2007)
  15. Couteau C, et. al. Study of the efficacy of 18 sun filters authorized in European Union tested in vitro. Pharmazie. (2007)
  16. Berkman MS, Yazan Y. A validated HPLC method for the determination of octocrylene in solid lipid nanoparticle systems. Pharmazie. (2011)
  17. Berkman MS, Yazan Y. Solid lipid nanoparticles: a possible vehicle for zinc oxide and octocrylene. Pharmazie. (2012)
  18. Niculae G, et. al. Rice bran and raspberry seed oil-based nanocarriers with self-antioxidative properties as safe photoprotective formulations. Photochem Photobiol Sci. (2014)
  19. Seité S, et. al. A full-UV spectrum absorbing daily use cream protects human skin against biological changes occurring in photoaging. Photodermatol Photoimmunol Photomed. (2000)
  20. Couteau C, et. al. UV filters, ingredients with a recognized anti-inflammatory effect. PLOS ONE. (2012)
  21. Stege H, et. al. Evaluation of the capacity of sunscreens to photoprotect lupus erythematosus patients by employing the photoprovocation test. Photodermatol Photoimmunol Photomed. (2000)
  22. Couteau C, et. al. Study of the photostability of 18 sunscreens in creams by measuring the SPF in vitro. J Pharm Biomed Anal. (2007)
  23. Bonda CA. Research pathways to photostable sunscreens. Cosmet Toil. (2008)
  24. Gaspar LR, Maia Campos PM. Evaluation of the photostability of different UV filter combinations in a sunscreen. Int J Pharm. (2006)
  25. Scalia S, Mezzena M. Incorporation in lipid microparticles of the UVA filter, butyl methoxydibenzoylmethane combined with the UVB filter, octocrylene: effect on photostability. AAPS PharmSciTech. (2009)
  26. Niculae G, et. al. Coencapsulation of butyl-methoxydibenzoylmethane and octocrylene into lipid nanocarriers: UV performance, photostability and in vitro release. Photochem Photobiol. (2013)
  27. Damiani E, et. al. Changes in ultraviolet absorbance and hence in protective efficacy against lipid peroxidation of organic sunscreens after UVA irradiation. J Photochem Photobiol B. (2006)
  28. Gaspar LR, Campos PM. Photostability and efficacy studies of topical formulations containing UV-filters combination and vitamins A, C and E. Int J Pharm. (2007)
  29. Al-Rawashdeh NA, Al-Sadeh KS, Al-Bitar MB. Physicochemical study on microencapsulation of hydroxypropyl-beta-cyclodextrin in dermal preparations. Drug Dev Ind Pharm. (2010)
  30. US Food and Drug Administration. CFR - Code of Federal Regulations Title 21, Part 352, Subpart B, Section 352.10. Code of Federal Regulations. (2013)
  31. European Commission. List of UV filters allowed in cosmetic products. Cosmetics Directive. (2011)
  32. Nash JF. Human safety and efficacy of ultraviolet filters and sunscreen products. Dermatol Clin. (2006)
  33. Odio MR, et. al. Evaluation of subchronic (13 week), reproductive, and in vitro genetic toxicity potential of 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate (Octocrylene). Fundam Appl Toxicol. (1994)
  34. Gilaberte Y, Carrascosa JM. Sun protection in children: realities and challenges. Actas Dermosifiliogr. (2014)
  35. Schlumpf M, et. al. Exposure patterns of UV filters, fragrances, parabens, phthalates, organochlor pesticides, PBDEs, and PCBs in human milk: correlation of UV filters with use of cosmetics. Chemosphere. (2010)
  36. Hanson KM, Gratton E, Bardeen CJ. Sunscreen enhancement of UV-induced reactive oxygen species in the skin. Free Radic Biol Med. (2006)
  37. Karlsson I, et. al. Clinical and experimental studies of octocrylene's allergenic potency. Contact Dermatitis. (2011)
  38. Darvay A, et. al. Photoallergic contact dermatitis is uncommon. Br J Dermatol. (2001)
  39. Shaw T, et. al. True photoallergy to sunscreens is rare despite popular belief. Dermatitis. (2010)
  40. European Multicentre Photopatch Test Study (EMCPPTS) Taskforce. A European multicentre photopatch test study. Br J Dermatol. (2012)
  41. Travassos AR, et. al. Non-fragrance allergens in specific cosmetic products. Contact Dermatitis. (2011)
  42. Delplace D, Blondeel A. Octocrylene: really non-allergenic? Contact Dermatitis. (2006)
  43. Madan V, Beck MH. Contact allergy to octocrylene in sunscreen with recurrence from passive transfer of a cosmetic. Contact Dermatitis. (2005)
  44. Carrotte-Lefebvre I, et. al. Contact allergy to octocrylene. Contact Dermatitis. (2003)
  45. Bennàssar A, et. al. Two cases of photocontact allergy to the new sun filter octocrylene. Dermatol Online J. (2009)
  46. Avenel-Audran M, et. al. Octocrylene, an emerging photoallergen. Arch Dermatol. (2010)
  47. Dumon D, et. al. Allergic contact dermatitis caused by octocrylene in a young child. Contact Dermatitis. (2012)
  48. Macías E, et. al. Allergic contact dermatitis due to sensitisation to sunscreen in two infants. Allergol Immunopathol (Madr). (2013)
  49. Agustí-Mejias A, et. al. Contact allergy to octocrylene in children: a report of 2 cases. Actas Dermosifiliogr. (2014)
  50. Karlsson I, et. al. Investigation of the sunscreen octocrylene's interaction with amino acid analogs in the presence of UV radiation. Photochem Photobiol. (2012)
  51. Stiefel C, Schwack W. Rapid screening method to study the reactivity of UV filter substances towards skin proteins by high-performance thin-layer chromatography. Int J Cosmet Sci. (2013)
  52. Foti C, et. al. Allergic and photoallergic contact dermatitis from ketoprofen: evaluation of cross-reactivities by a combination of photopatch testing and computerized conformational analysis. Curr Pharm Des. (2008)
  53. Matsumoto H, Adachi S, Suzuki Y. Estrogenic activity of ultraviolet absorbers and the related compounds. Yakugaku Zasshi. (2005)
  54. Ozáez I, Martínez-Guitarte JL, Morcillo G. Effects of in vivo exposure to UV filters (4-MBC, OMC, BP-3, 4-HB, OC, OD-PABA) on endocrine signaling genes in the insect Chironomus riparius. Sci Total Environ. (2013)
  55. Brand RM, Spalding M, Mueller C. Sunscreens can increase dermal penetration of 2,4-dichlorophenoxyacetic acid. J Toxicol Clin Toxicol. (2002)
  56. Brand RM, et. al. Sunscreens containing physical UV blockers can increase transdermal absorption of pesticides. Toxicol Ind Health. (2003)
  57. Pont AR, et. al. Effects of active sunscreen ingredient combinations on the topical penetration of the herbicide 2,4-dichlorophenoxyacetic acid. Toxicol Ind Health. (2003)
  58. Pont AR, Charron AR, Brand RM. Active ingredients in sunscreens act as topical penetration enhancers for the herbicide 2,4-dichlorophenoxyacetic acid. Toxicol Appl Pharmacol. (2004)