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homosalate
Sign in to saveHomosalate 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.
Chemical data
- Formula
- C16H22O3
- Molecular weight
- 262.34 g/mol
- IUPAC name
- (3,3,5-trimethylcyclohexyl) 2-hydroxybenzoate
- SMILES
- CC1CC(CC(C1)(C)C)OC(=O)C2=CC=CC=C2O
- InChIKey
- WSSJONWNBBTCMG-UHFFFAOYSA-N
- XLogP
- 5
- Polar surface area
- 46.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
166 papers- Homosalate boosts the release of tumour-derived extracellular vesicles with protection against anchorage-loss property.Journal of extracellular vesicles · 2022
- Homosalate and ERK Knockdown in the Modulation of Aurelia coerulea Metamorphosis by Regulating the PI3K Pathway and ERK Pathway.Current issues in molecular biology · 2024
- Sunscreens.2006
- Toxicokinetics of homosalate in humans after dermal application: applicability of oral-route data for exposure assessment by human biomonitoring.Archives of toxicology · 2024
- Effect of Sunscreen Application on Plasma Concentration of Sunscreen Active Ingredients: A Randomized Clinical Trial.JAMA · 2020
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 262.157
- Has use
- sunscreen
Show 4 more facts
- chemical formula
- C₁₆H₂₂O₃
- canonical SMILES
- CC1CC(CC(C1)(C)C)OC(=O)C2=CC=CC=C2O
- Commons category
- Homosalate
- found in taxon
- Camellia sinensis
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
2 sectionsContents
- Safety
- References
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.
==Safety== Homosalate 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.
Excerpted from Wikipedia’s “homosalate” article, available under the CC BY-SA 4.0 licence.