2-Ethylhexyl salicylate

Last updated
Octyl salicylate
2-Ethylhexyl salicylate Structural Formula V1.svg
2-Ethylhexyl salicylate 3D ball.png
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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 X mark.svgN
    Key: FMRHJJZUHUTGKE-UHFFFAOYSA-N X mark.svgN
  • 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.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability (yellow): no hazard codeSpecial hazards (white): no code
1
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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

According to the classification provided by companies to ECHA in REACH registrations this substance is very toxic to aquatic life with long lasting effects and is suspected of damaging the unborn child. [2]

In 2020 the ECHA decided that a fish sexual development test of the chemical was necessary, because the compound may be an endocrine disruptor. [3]

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. [4]

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. [5] [6]

In 2007 octyl salicylate and all other salicylates were found to have a good safety profile. [7] 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. [8]

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. [9]


Notes

  1. ↑ "UV Radiation". The Skin Cancer Foundation. Retrieved 2025-02-25.
  2. ↑ "Substance Information - ECHA". echa.europa.eu (in German). Retrieved 2025-02-25.
  3. ↑ "Board of Appeal decisions concerning vertebrate animal testing on cosmetic ingredients". echa.europa.eu.
  4. ↑ "Animal tests for makeup ingredients allowed". BBC News. 5 May 2023.
  5. ↑ "CURIA - Documents".
  6. ↑ "CURIA - Documents".
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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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