Phenyl salicylate

"Salol" redirects here. Salol may also refer to Salol, Minnesota.
Phenyl salicylate[1]
Names
IUPAC name
Phenyl 2-hydroxybenzoate
Other names
Salol
Identifiers
ATC code G04BX12
118-55-8 Yes
ChEBI CHEBI:34918 
ChEMBL ChEMBL1339216 
ChemSpider 8058 
EC number 204-259-2
Jmol-3D images Image
KEGG C14163 
MeSH C026041
PubChem 8361
Properties
C13H10O3
Molar mass 214.22 g/mol
Appearance White solid
Density 1.25 g/cm3
Melting point 41.5 °C (106.7 °F; 314.6 K)
Boiling point 173 °C (343 °F; 446 K) at 12 mmHg
1 g/6670 mL
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Phenyl salicylate, or salol, is a chemical substance, introduced in 1886 by Marceli Nencki of Basel. It can be created by heating salicylic acid with phenol. Once used in sunscreens, phenyl salicylate is now used in the manufacture of some polymers, lacquers, adhesives, waxes and polishes.[1] It is also used frequently in school laboratory demonstrations on how cooling rates affect crystal size in igneous rocks.

Salol reaction

In the salol reaction, phenyl salicylate reacts with o-toluidine in 1,2,4-trichlorobenzene at elevated temperatures to the corresponding amide o-Salicylotoluide.[2] Salicylamides are one type of drug.

Medical

It has been used as an antiseptic[3] based on the antibacterial activity upon hydrolysis in the small intestine.

It acts as a mild analgesic.[4]

References

  1. ↑ 1.0 1.1 Merck Index, 11th Edition, 7282.
  2. ↑ Allen, C. F. H.; VanAllan, J. (1946). "SALICYL-o-TOLUIDE" (PDF). Org. Synth. 26: 92.; Coll. Vol. 3, p. 765
  3. ↑ Walter Sneader (2005). Drug discovery: a history. John Wiley and Sons. pp. 358–. ISBN 978-0-471-89980-8. Retrieved 28 October 2010.
  4. ↑ Judith Barberio (4 September 2009). Nurse's Pocket Drug Guide, 2010. McGraw Hill Professional. pp. 57–. ISBN 978-0-07-162743-6. Retrieved 28 October 2010.