Homosalate

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Homosalate[1]
Skeletal formula
Space-filling model
Identifiers
CAS number 118-56-9 YesY
PubChem 8362
ChemSpider 8059 YesY
KEGG D04450 YesY
Jmol-3D images Image 1
Properties
Molecular formula C16H22O3
Molar mass 262.36 g/mol
Density 1.045 g/cm3
Melting point <25 °C
Boiling point 161-165 °C at 4 mmHg
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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[edit]

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 evidence that homosalate (and other UV filters) can break down into more toxic products.[9][not in citation given]

References[edit]

  1. ^ Homosalate, Merck Index, 11th Edition, 4660
  2. ^ Homosalate, ChemIDplus
  3. ^ Rougier A, Dupuis D, Lotte C, Roguet R, Wester RC, Maibach HI (1986). "Regional variation in percutaneous absorption in man: measurement by the stripping method". Arch. Dermatol. Res. 278 (6): 465–9. PMID 3789805. 
  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