Phenyl salicylate

Phenyl salicylate, or salol, is the organic compound with the formula C6H5O2C6H4OH. It is a
white solid. It is occasionally used in sunscreens and as an antiseptic.[3]
 Phenyl salicylate
[1]

Names

Preferred IUPAC name

Phenyl 2-hydroxybenzoate

Other names
Salol

Identifiers

CAS Number 118-55-8 (https://commonchemistry.cas.org/deta

il?cas_rn=118-55-8)  

3D model (JSmol) Interactive image (https://chemapps.stolaf.edu/j

mol/jmol.php?model=O%3DC%28Oc2ccccc2%29
c1c%28O%29cccc1)

ChEBI CHEBI:34918 (https://www.ebi.ac.uk/chebi/searc

hId.do?chebiId=34918)  

ChEMBL ChEMBL1339216 (https://www.ebi.ac.uk/chembl

db/index.php/compound/inspect/ChEMBL1339
216)  

ChemSpider 8058 (https://www.chemspider.com/Chemical-Str

ucture.8058.html)  

ECHA InfoCard 100.003.873 (https://echa.europa.eu/substance-i

 nformation/-/substanceinfo/100.003.873)
EC Number 204-259-2

KEGG C14163 (https://www.kegg.jp/entry/C14163)  

MeSH C026041 (https://www.nlm.nih.gov/cgi/mesh/20

14/MB_cgi?mode=&term=C026041)

PubChem CID 8361 (https://pubchem.ncbi.nlm.nih.gov/compou

nd/8361)

UNII 28A37T47QO (https://fdasis.nlm.nih.gov/srs/srsd

irect.jsp?regno=28A37T47QO)  

CompTox Dashboard (EPA) DTXSID6021957 (https://comptox.epa.gov/dashb

oard/chemical/details/DTXSID6021957)

InChI
InChI=1S/C13H10O3/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9,14H 
Key: ZQBAKBUEJOMQEX-UHFFFAOYSA-N 
InChI=1/C13H10O3/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9,14H
Key: ZQBAKBUEJOMQEX-UHFFFAOYAI

SMILES
O=C(Oc2ccccc2)c1c(O)cccc1

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
ATC code G04BX12 (WHO (https://www.whocc.no/atc_ddd_
index/?code=G04BX12) )

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).
 verify (https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=412457168&page2=
Phenyl+salicylate)  (what is   ?)
Infobox references

Production and reactions

The title compound was synthesized first in 1883 by the Polish chemist and doctor Marceli
Nencki (who didn't publish his findings) and then independently in 1885 by the German chemist
Richard Seifert (de) (1861–1919) (who did publish his findings). It is synthesized by heating
salicylic acid with phenol in the presence of phosphoryl chloride.[4] It also arises from heating
salicylic acid:[5]

2 HOC6H4CO2H → C6H5O2C6H4OH + CO2 + H2O

The conversion entails dehydration and decarboxylation. Heating phenyl salicylate in turn gives
xanthone.[6][3]

2 C6H5O2C6H4OH → 2 C6H5OH + O[C6H4]2CO + CO2

In this conversion, phenol is produced as well as carbon dioxide.

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.[7] Salicylamides are a type
of drug.

Medical
It has been used as an antiseptic[8] based on the antibacterial activity upon hydrolysis in the
small intestine.

It acts as a mild analgesic.[9]

History

The Swiss physician Hermann Sahli (sometimes spelled "Saly") (1856–1933) sought a
substitute for sodium salicylate, which was used as a treatment for rheumatoid arthritis but
which wasn't tolerated by some patients. So Dr. Sahli asked the Polish chemist and doctor
Marceli Nencki of Bern, Switzerland if Nencki knew of a salicylate compound that lacked sodium
salicylate's side effects.[10] Nencki recommended phenyl salicylate, which he had synthesized
circa 1883.[11][12] While Nencki had been investigating how phenyl salicylate behaved in the body,
he hadn't published his findings.[13] Meanwhile, the German chemist Richard Seifert (de) (1861–
1919), a student of the German chemist Rudolf Wilhelm Schmitt (de) (1830–1898),[14]
independently synthesized phenyl salicylate in 1885.[15] In 1885, Seifert accepted a position at
the Heyden chemical corporation (de) of Radebeul, Germany, which manufactured salicylic
acid.[16] The United States granted to Nencki and Seifert a patent for the production of phenyl
salicylate,[17] whereas Germany granted a patent for its production to Nencki and the Heyden
corporation.[18] The Heyden company subsequently sold phenyl salicylate as a pharmaceutical,
under the commercial name "Salol",[19] a contraction of "SALicylate of phenOL".[20] Among other
applications,[21] Salol was used as an orally administered antiseptic for the small intestine,
where the compound is hydrolyzed into salicylic acid and phenol.[17]

See also

Phenyl salicylate is used in school laboratory demonstrations on how cooling rates affect crystal
size in igneous rocks, and can be used to demonstrate seed crystal selectiveness.

References

1. Merck Index, 11th Edition, 7282.

2. ChemBK Chemical Database http://www.chembk.com/en/chem/Phenyl%20salicylate