Phenyl salicylate

Phenyl salicylate, or salol, is a chemical substance, introduced c. 1883 by Marceli Nencki of Basel. It is synthesized 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] Commonly it is used in school laboratory demonstrations on how cooling rates affect crystal size in igneous rocks. Can be used to demonstrate seed crystal selectiveness. Salol is also used as an internal antiseptic and as a mild analgesic.[3].

Phenyl salicylate[1]
Names
IUPAC name
Phenyl 2-hydroxybenzoate
Other names
Salol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.873
EC Number
  • 204-259-2
KEGG
MeSH C026041
PubChem CID
Properties
Chemical formula
 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
Solubility in water
 1 g/6670 mL
Magnetic susceptibility (χ)
 -123.2·10−6 cm3/mol
Refractive index (nD)
 1.615[2]
Pharmacology
G04BX12 (WHO)
Hazards
Flash point 137.3[2] °C (279.1 °F; 410.4 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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.[4] Salicylamides are one type of drug.

Medical

It has been used as an antiseptic[5] based on the antibacterial activity upon hydrolysis in the small intestine.

It acts as a mild analgesic.[6]

References
  1. Merck Index, 11th Edition, 7282.
  2. ChemBK Chemical Database http://www.chembk.com/en/chem/Phenyl%20salicylate
  3. Holden, Alan. "Physics: Crystals 1958". Bell Laboratories - PSSC Physical Science Study Committee. Retrieved 28 January 2018.
  4. Allen, C. F. H.; VanAllan, J. (1946). "SALICYL-o-TOLUIDE" (PDF). Organic Syntheses. 26: 92.; Collective Volume, 3, p. 765
  5. Walter Sneader (2005). Drug discovery: a history. John Wiley and Sons. pp. 358–. ISBN 978-0-471-89980-8. Retrieved 28 October 2010.
  6. 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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.