Homosalate

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A synthetic chemical that replaces the phenolic compounds used in sunscreens. Poisonng has been reported when the chemical is absorbed into the skin.

Homosalate (Wikipedia)

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. 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.

Homosalate
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)
Melting point < -20 °C
Boiling point 181–185 °C (358–365 °F; 454–458 K)
0.4 mg/L
Hazards
Flash point 171 °C (340 °F; 444 K)
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 ?)
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