Homosalate

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Homosalate[1]
Skeletal formula
Space-filling model
Names
IUPAC name
3,3,5-Trimethylcyclohexyl 2-hydroxybenzoate
Other names
Homosalate
Identifiers
118-56-9 YesY
ChemSpider 8059 YesY
Jmol 3D model Interactive image
KEGG D04450 YesY
PubChem 8362
UNII V06SV4M95S YesY
  • InChI=1S/C16H22O3/c1-11-8-12(10-16(2,3)9-11)19-15(18)13-6-4-5-7-14(13)17/h4-7,11-12,17H,8-10H2,1-3H3 YesY
    Key: WSSJONWNBBTCMG-UHFFFAOYSA-N YesY
  • InChI=1/C16H22O3/c1-11-8-12(10-16(2,3)9-11)19-15(18)13-6-4-5-7-14(13)17/h4-7,11-12,17H,8-10H2,1-3H3
    Key: WSSJONWNBBTCMG-UHFFFAOYAJ
  • O=C(OC1CC(CC(C1)(C)C)C)c2ccccc2O
Properties
C16H22O3
Molar mass 262.36 g/mol
Density 1.045 g/cm3
Melting point <25 °C
Boiling point 161 to 165 °C (322 to 329 °F; 434 to 438 K) at 4 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Homosalate is an organic compound used in some sunscreens. It is an ester formed from salicylic acid and 3,3,5-trimethylcyclohexanol, a derivative of cyclohexanol. Contained in 45% of U.S. sunscreens, it is used as a chemical UV filter.[2] The salicylic acid portion of the molecule absorbs ultraviolet rays with a wavelength from 295 nm to 315 nm, protecting the skin from sun damage. The hydrophobic cyclohexanol portion provides greasiness that prevents it from dissolving in water.

Safety

Lua error in package.lua at line 80: module 'strict' not found. Similar to other UV filter compounds,[3] more homosalate is absorbed into the stratum corneum of the face (25% of applied dose) versus back of volunteers.[4] Homosalate has been identified as an antiandrogen in vitro,[5] as well as having estrogenic activity toward estrogen receptors α,[6] and general in vitro estrogenic activity.[7] Homosalate has been shown to be an antagonist toward androgen and estrogen receptors in vitro.[8] There is also heavy evidence that homosalate, (and other UV filters) can break down into more toxic products.[9][not in citation given]

No evidence of toxicity or side effects have been documented in vivo.

References

  1. ↑ Homosalate, Merck Index, 11th Edition, 4660
  2. ↑ Homosalate, ChemIDplus
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ [1] Benson et al., 2005
  5. ↑ [2] Ma et al., 2003
  6. ↑ [3] Gomez et al., 2005
  7. ↑ [4] Schlumpf et al., 2004
  8. ↑ [5] Schreurs et al., 2005
  9. ↑ [6] Klimova et al., 2013. Current problems in the use of organic UV filters to protect skin from excessive sun exposure. Acta Chimica Slovaca, 6(1):82—88, doi:10.2478/acs-2013-0014


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