Homosalate

Homosalate[1]
Skeletal formula
Space-filling model
Names
IUPAC name
3,3,5-Trimethylcyclohexyl 2-hydroxybenzoate
Other names
Homosalate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.874 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: WSSJONWNBBTCMG-UHFFFAOYSA-N checkY
  • 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 262.349 g·mol−1
Density 1.05 g/cm3 (20 °C)[2]
Melting point < -20 °C[2]
Boiling point 181–185 °C (358–365 °F; 454–458 K)[2]
0.4 mg/L
Hazards
Flash point 171 °C (340 °F; 444 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Homosalate is an organic compound used in some sunscreens. It is made by the Fischer–Speier esterification of salicylic acid and 3,3,5-trimethylcyclohexanol, the latter being a hydrogenated derivative of isophorone. Contained in 45% of U.S. sunscreens, it is used as a chemical UV filter.[3] 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 trimethyl cyclohexyl group provides greasiness that prevents it from dissolving in water.

  1. ^ Homosalate, Merck Index, 11th Edition, 4660.
  2. ^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ Homosalate, ChemIDplus.