Octyl Salicylate

Octyl salicylate
Names
	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;
Identifiers
CAS Number	118-60-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL117388 ;
ChemSpider	8061 ;
PubChem CID	8364;
UNII	4X49Y0596W ;
	InChI InChI=1S/C15H22O3/c1-3-5-8-12(4-2)11-18-15(17)13-9-6-7-10-14(13)16/h6-7,9-10,12,16H,3-5,8,11H2,1-2H3 Key: FMRHJJZUHUTGKE-UHFFFAOYSA-N ; InChI=1/C15H22O3/c1-3-5-8-12(4-2)11-18-15(17)13-9-6-7-10-14(13)16/h6-7,9-10,12,16H,3-5,8,11H2,1-2H3 Key: FMRHJJZUHUTGKE-UHFFFAOYAL;
	SMILES CCCCC(CC)COC(=O)C1=CC=CC=C1O;
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).
	verify (what is ?)
	Infobox references

Octyl salicylate, or 2-ethylhexyl 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

Octisalate and all other salicylates have a good safety profile.^[2] It is often used to improve affinity and reduce photodegradation of other sunscreen ingredients (such as oxybenzone and avobenzone), and <1% of the applied dose of Octisalate penetrates through the skin. Although Octisalate is a weaker UVB absorber it has superior stability than some other sunscreen active ingredients^[3] and 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.^[4]

Notes

↑ Skin cancer foundation: Understanding UVA and UVB
↑ 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. http://www.bioline.org.br/abstract?dv07028.
↑ 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. https://link.springer.com/article/10.1007/s10971-020-05417-6.
↑ 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. https://onlinelibrary.wiley.com/doi/abs/10.1111/ajd.12597.

References

"The Skin Cancer Foundation's Guide to Sunscreens". Skin Cancer Foundation. 2011. http://www.skincancer.org/the-scfs-guide-to-sunscreens.html.

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[1] Skin cancer foundation: Understanding UVA and UVB

[2] 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. http://www.bioline.org.br/abstract?dv07028.

[3] 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. https://link.springer.com/article/10.1007/s10971-020-05417-6.

[4] 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. https://onlinelibrary.wiley.com/doi/abs/10.1111/ajd.12597.

v t e Sunscreening agents approved by the US FDA or other agencies
UVA: 400–315 nm UVB: 315–290 nm chemical agents unless otherwise noted
UVA filters	Avobenzone (Parsol 1789) Bisdisulizole disodium (Neo Heliopan AP) Diethylamino hydroxybenzoyl hexyl benzoate (Uvinul A Plus) Ecamsule (Mexoryl SX) Menthyl anthranilate
UVB filters	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
UVA+UVB filters	Bemotrizinol (Tinosorb S) Benzophenones 1–12 Dioxybenzone Drometrizole trisiloxane (Mexoryl XL) Iscotrizinol (Uvasorb HEB) Octocrylene Oxybenzone (Eusolex 4360) Sulisobenzone hybrid (chemical/physical): Bisoctrizole (Tinosorb M / Eversorb M) physical: Titanium dioxide Zinc oxide
See also: Photoprotection, Sun protective clothing, Sun tanning, and Sunburn