Homosalate

Source: Wikipedia, the free encyclopedia.
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

hydrophobic
trimethyl cyclohexyl group provides greasiness that prevents it from dissolving in water.

Safety

Similar to other UV filter compounds,[4] more homosalate is absorbed into the uppermost stratum corneum (ie, the stratum disjunctum) of the face (25% of applied dose) versus back of volunteers. This amounted to approximately two to three times the amount of sunscreen that was present in the superficial stratum corneum layers of the face compared with the back. There was no homosalate detected in the urine samples or blood plasma samples of the volunteers in this study.[5][6]

Homosalate has been identified as an antiandrogen in vitro,[7] as well as having estrogenic activity toward estrogen receptors α,[8] and general in vitro estrogenic activity.[9] Homosalate has been shown to be an antagonist toward androgen and estrogen receptors in vitro.[10] Some work has shown that organic UV filters in general can present concerns.[11]

There is no in vivo evidence of toxicity, endocrine disfunction or adverse effects; and none of these adverse events have ever been reported to occur in humans.

An in vivo study involving repeated

zebra fish
also found no estrogenic effects after being continuously exposed to homosalate for 96 hours straight. The
phototoxic or photosensitive effects when applied topically.[6]

References

  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.
  4. S2CID 24610879
    .
  5. PMID 18360561
    .
  6. ^ a b "OPINION on Homosalate" (PDF). Scientific Committee on Consumer Safety. June 2021.
  7. PMID 12730620
    .
  8. S2CID 41796996
    .
  9. PMID 15458796
    .
  10. PMID 15537743
    .
  11. S2CID 42677951
    .
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