Octisalate

Octisalate is a weak, but stable and safe organic sunscreen that is usually used to augment other UVB absorbers in cosmetics and skin care products.

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

A weak UVB absorber that does not inhibit DNA damage, but has good skin cancer chemoprevention potential.

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Scientific Research


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Table of contents:

1. Sources

Octisalate, short for octyl salicylate, is a colourless, viscous and oil-soluble liquid that can be synthesized by esterifying salicylic acid with 2-ethylhexanol.[1] It is a chemical sunscreen that protects against UVB radiation,[2] and has also been used in cosmetic products as a fragrance ingredient.[3]

Surface waters that receive wastewater effluents may contain sunscreens including octisalate that are washed off during bathing, as has been shown in Japan.[4] Octisalate has also been detected in indoor dust samples from Spain.[5]

2. Skin penetration

Data obtained from in vitro experiments suggest that the permeation of octisalate through human skin is quite low. When applied as a finite dose in a hydroalcoholic formulation containing 5% octisalate or in an oil-in-water emulsion containing 2.7% octisalate, only about 0.6% of the dose was absorbed over 48 hours.[6][7] When 3% octisalate in petrolatum or an oil-in-water emulsion-gel was applied to the backs of 4 human volunteers, 40-50% of the applied dose in the emulsion-gel, and 15% of the applied dose in petrolatum, was found in the first 5 strips of the stratum corneum after 30 minutes.[8]

Application temperature does not affect the adsorption of octisalate to the stratum corneum of the skin.[9]

3. Effects on the skin

3.1 Photoprotection

Octisalate is a UV filter that absorbs in the range of 280-320 nm, with an absorption maximum that varies between 300-310 nm depending on the solvent.[10][11] In a comparison of 18 sun filters at the highest concentrations authorized by the European Union, it was ranked third-last in terms of efficacy.[12]

Although octisalate does not inhibit the formation of thymine dimers in the skin,[13] it was the most potent sunscreen among 13 others with regards to its skin cancer chemoprevention potential, as measured by an in vitro assay.[14] The combination of octisalate, oxybenzone and octinoxate in a SPF 29 sunscreen, was able to prevent UVB-induced local immunosuppression in human skin,[15] but another formulation containing the same combination of sunscreens was not completely effective in protecting the skin against UV-induced oxidative stress and inflammation.[16]

Octisalate is not effective in protecting against UVA radiation[17][18] and needs to be combined with a UVA filter such as avobenzone in order to provide broad spectrum protection.

4. Stability

Octisalate is acceptably stable in water samples containing low concentrations of chlorine.[19] UV irradiation for 2-3 hours leads to a 15% reduction in the amount of octisalate recoverable.[20][21]

5. Safety

Octisalate is a permitted sunscreen in the United States and in the European Union, where it is allowed up to a concentration of 5%.[22][23]

5.1 Adverse skin reactions

4% octisalate in petrolatum was neither irritating or sensitizing when applied to the backs of 23 male volunteers in a human maximization test, though mild erythema lasting 24 hours had previously been observed when rabbit skin was exposed to pure octisalate.[3]

There are a few isolated reports of allergic contact dermatitis or contact sensitivity to octisalate in topical products.[24][25][26]

5.2 No evidence of endocrine disruption

Unlike homosalate, octisalate did not exhibit estrogenic activity in a bioassay.[27]

5.3 Penetration enhancer

Octisalate can act as a dermal penetration enhancer.[28][29][30] It increased the penetration of the herbicide 2,4-dichlorophenoxyacetic acid in vitro, which may pose a risk to agricultural workers who are encouraged to use sunscreens to decrease their risk of UV-related skin cancer.[31]

Scientific References


  1. Villa C, et. al. Eco-friendly methodologies for the synthesis of some aromatic esters, well-known cosmetic ingredients. Int J Cosmet Sci. (2005)
  2. Yousef Agha N, Haidar S, Al‐Khayat MA. Development and Validation of RP-HPLC Method for Analysis of Four UV Filters in Sunscreen Products. Int J Pharm Sci Rev Res. (2013)
  3. Lapczynski A, et. al. Fragrance material review on ethyl hexyl salicylate. Food Chem Toxicol. (2007)
  4. Kameda Y, Kimura K, Miyazaki M. Occurrence and profiles of organic sun-blocking agents in surface waters and sediments in Japanese rivers and lakes. Environ Pollut. (2011)
  5. Negreira N, et. al. Determination of selected UV filters in indoor dust by matrix solid-phase dispersion and gas chromatography-tandem mass spectrometry. J Chromatogr A. (2009)
  6. Walters KA, et. al. Percutaneous penetration of octyl salicylate from representative sunscreen formulations through human skin in vitro. Food Chem Toxicol. (1997)
  7. Walters KA, Watkinson AC, Brain KR. In vitro skin permeation evaluation: the only realistic option. Int J Cosmet Sci. (1998)
  8. Treffel P, Gabard B. Skin penetration and sun protection factor of ultra-violet filters from two vehicles. Pharm Res. (1996)
  9. Clarys P, et. al. There is no influence of a temperature rise on in vivo adsorption of UV filters into the stratum corneum. J Dermatol Sci. (2001)
  10. de Groot AC, Weyland JW, Nater JP. Cosmetics for the body and parts of the body. Unwanted Effects of Cosmetics and Drugs Used in Dermatology, Issue 282. (1994)
  11. Agrapidis-Paloympis LE, Nash RA. The effect of solvents on the ultraviolet absorbance of sunscreens. J Soc Cosmet Chem. (1987)
  12. Couteau C, et. al. Study of the efficacy of 18 sun filters authorized in European Union tested in vitro. Pharmazie. (2007)
  13. McVean M, Liebler DC. Prevention of DNA photodamage by vitamin E compounds and sunscreens: roles of ultraviolet absorbance and cellular uptake. Mol Carcinog. (1999)
  14. Kapadia GJ, et. al. Evaluation of skin cancer chemoprevention potential of sunscreen agents using the Epstein-Barr virus early antigen activation in vitro assay. Int J Cosmet Sci. (2013)
  15. Whitmore SE, Morison WL. Prevention of UVB-induced immunosuppression in humans by a high sun protection factor sunscreen. Arch Dermatol. (1995)
  16. Vilela FM, et. al. Sunscreen protection against ultraviolet-induced oxidative stress: evaluation of reduced glutathione levels, metalloproteinase secretion, and myeloperoxidase activity. Pharmazie. (2013)
  17. Lowe NJ, et. al. Indoor and outdoor efficacy testing of a broad-spectrum sunscreen against ultraviolet A radiation in psoralen-sensitized subjects. J Am Acad Dermatol. (1987)
  18. Gange RW, et. al. Efficacy of a sunscreen containing butyl methoxydibenzoylmethane against ultraviolet A radiation in photosensitized subjects. J Am Acad Dermatol. (1986)
  19. Negreira N, et. al. Study of some UV filters stability in chlorinated water and identification of halogenated by-products by gas chromatography-mass spectrometry. J Chromatogr A. (2008)
  20. Gaspar LR, Maia Campos PM. Evaluation of the photostability of different UV filter combinations in a sunscreen. Int J Pharm. (2006)
  21. Vilela FM, et. al. Effect of ultraviolet filters on skin superoxide dismutase activity in hairless mice after a single dose of ultraviolet radiation. Eur J Pharm Biopharm. (2012)
  22. US Food and Drug Administration. CFR - Code of Federal Regulations Title 21, Part 352, Subpart B, Section 352.10. Code of Federal Regulations. (2013)
  23. European Commission. List of UV filters allowed in cosmetic products. Cosmetics Directive. (2011)
  24. Shaw DW. Allergic contact dermatitis from octisalate and cis-3-hexenyl salicylate. Dermatitis. (2006)
  25. Singh M, Beck MH. Octyl salicylate: a new contact sensitivity. Contact Dermatitis. (2007)
  26. Mortz CG, et. al. Allergic contact dermatitis from ethylhexyl salicylate and other salicylates. Dermatitis. (2010)
  27. Jiménez-Díaz I, et. al. Simultaneous determination of the UV-filters benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in human placental tissue by LC-MS/MS. Assessment of their in vitro endocrine activity. J Chromatogr B Analyt Technol Biomed Life Sci. (2013)
  28. Nicolazzo JA, et. al. Synergistic enhancement of testosterone transdermal delivery. J Control Release. (2005)
  29. Morgan TM, et. al. Enhanced skin permeation of sex hormones with novel topical spray vehicles. J Pharm Sci. (1998)
  30. Santos P, et. al. Influence of penetration enhancer on drug permeation from volatile formulations. Int J Pharm. (2012)
  31. 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)