2-Ethylhexyl salicylate

2-Ethylhexyl salicylate, 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.

Octyl salicylate
Structural formula of octyl salicylate
Ball-and-stick model of the octyl salicylate molecule
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.877
UNII
  • 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 ☒N
    Key: FMRHJJZUHUTGKE-UHFFFAOYSA-N ☒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
  • CCCCC(CC)COC(=O)C1=CC=CC=C1O
Properties
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)
NFPA 704 four-colored diamond
1
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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
  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.
  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. S2CID 221937086.
  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. S2CID 32838625.

References
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