2-Ethylhexyl salicylate
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Names | |
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IUPAC name 2-ethylhexyl 2-hydroxybenzoate | |
Other names octisalate; 2-ethylhexyl salicylate; ethyl hexyl salicylate; 2-ethylhexyl ester salicylic acid; salicylic acid, 2-ethylhexyl ester; benzoic acid, 2-hydroxy-, 2-ethylhexyl ester; 2-ethylhexyl ester benzoic acid, 2-hydroxy-; 2-hydroxy- 2-ethylhexyl ester benzoic acid; | |
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ECHA InfoCard | 100.003.877 ![]() |
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InChI
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Properties | |
Chemical formula | C15H22O3 |
Molar mass | 250.33 g/mol |
Density | 1.014 g/cm3 |
Melting point | < 25 °C (77 °F; 298 K) |
Boiling point | 189 °C (372 °F; 462 K) |
Hazards | |
NFPA 704 (fire diamond) | ![]() 1 1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ![]() ![]() ![]() Infobox references |
2-Ethylhexyl salicylate also known as octisalate or octyl salicylate, is an organic compound used as an ingredient in sunscreens and cosmetics to absorb UVB (ultraviolet) rays from the sun.[1] It is an ester formed by the condensation of salicylic acid with 2-ethylhexanol. It is a colorless oily liquid with a slight floral odor.
The salicylate portion of the molecule absorbs ultraviolet light, protecting skin from the harmful effects of exposure to sunlight. The ethylhexanol portion is a fatty alcohol, adding emollient and oil-like (water resistant) properties.
Safety
In 2020 the ECHA decided that a fish sexual development test of the chemical was necessary, because the compound may be an endocrine disruptor.[2]
The compound was identified in a court case brought by German chemical company Symrise who claimed that the ingredient used in sunscreen did not require animal testing.
Symrise lost the appeal against a European Chemicals Agency (ECHA) decision that requires the German manufacturer to test sunscreen ingredients on animals.[3]
The Court of Justice of the European Union (CJEU) decision applies to two formerly approved ingredients used exclusively in sunscreens — UV filter homosalate and 2-ethylhexyl salicylate.[4][5]
In 2007 octyl salicylate and all other salicylates were found to have a good safety profile.[6] It is often used to improve affinity and reduce photodegradation of other sunscreen ingredients (such as oxybenzone and avobenzone), and under 1% of the applied dose of octyl salicylate penetrates through the skin. Although more stable, octyl salicylate is a weak organic UVB absorber.[7]
Octyl salicylate does not produce reactive oxygen species when exposed to sunlight. However, it does have some minor sensitization potential; with some individuals experiencing minimal to mild skin irritation.[8]
Notes
- ^ Skin cancer foundation: Understanding UVA and UVB
- ^ https://echa.europa.eu/documents/10162/13554/boa_decisions_reach_cosmetics_en.pdf/0c7da234-f467-6af9-c0cc-4dfb27cd0f9a [bare URL]
- ^ https://www.bbc.co.uk/news/science-environment-65484552 [bare URL]
- ^ https://curia.europa.eu/juris/document/document.jsf?text=&docid=286802&pageIndex=0&doclang=en&mode=lst&dir=&occ=first&part=1&cid=6696644 [bare URL]
- ^ https://curia.europa.eu/juris/document/document.jsf;jsessionid=13FF5B0EB4FF44663026FDE8D390B8ED?text=&docid=244529&pageIndex=0&doclang=en&mode=lst&dir=&occ=first&part=1&cid=6696105 [bare URL]
- ^ Rai, Reena; Srinivas, CR (2007). "Photoprotection". Indian Journal of Dermatology, Venereology and Leprology. 73 (2): 73–79. doi:10.4103/0378-6323.31889. PMID 17456910.
- ^ Ma, Haohua; Wang, Jianqiang; Zhang, Wenpei; Guo, Cheng (2021). "Synthesis of phenylalanine and leucine dipeptide functionalized silica-based nanoporous material as a safe UV filter for sunscreen". Journal of Sol-Gel Science and Technology. 97 (2): 466–478. doi:10.1007/s10971-020-05417-6. S2CID 221937086.
- ^ Yap, Francis HX; Chua, Hock C.; Tait, Clare P. (10 March 2017). "Active sunscreen ingredients in Australia". Australasian Journal of Dermatology. 58 (4): e160–e170. doi:10.1111/ajd.12597. PMID 28295176. S2CID 32838625.
References
- "The Skin Cancer Foundation's Guide to Sunscreens". Skin Cancer Foundation. 2011. Archived from the original on 23 November 2011. Retrieved 15 November 2011.
- v
- t
- e
- UVA: 400–315 nm
- UVB: 315–290 nm
- Chemical agents unless otherwise noted
- Amiloxate
- 4-Aminobenzoic acid (PABA)
- Cinoxate
- Ethylhexyl triazone (Uvinul T 150)
- Homosalate
- 4-Methylbenzylidene camphor (Enzacamene)
- Octyl methoxycinnamate (Octinoxate)
- Octyl salicylate (Octisalate)
- Padimate O (Escalol 507)
- Phenylbenzimidazole sulfonic acid (Ensulizole)
- Polysilicone-15 (Parsol SLX)
- Trolamine salicylate
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