Phenyl salicylate, or salol, is the
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula C
6H
5O
2C
6H
4OH. It is a white solid. It is occasionally used in sunscreens and as an antiseptic.
[
]
Production and reactions
The title compound was synthesized first in 1883 by the Polish chemist and doctor Marceli Nencki
Wilhelm Marceli Nencki (15 January 1847 in Boczki, Zduńska Wola County – 14 October 1901 in Saint Petersburg) was a Polish chemist and doctor.
Work
Nencki's main scientific interest concentrated on urea synthesis, the chemistry of purines a ...
(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
Salicylic acid is an organic compound with the formula HOC6H4CO2H. A colorless, bitter-tasting solid, it is a precursor to and a metabolite of aspirin (acetylsalicylic acid). It is a plant hormone, and has been listed by the EPA Toxic Substance ...
with phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...
in the presence of phosphoryl chloride
Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula . It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosp ...
. It also arises from heating salicylic acid:
:2HOC6H4CO2H → C6H5O2C6H4OH + CO2 + H2O
The conversion entails dehydration and decarboxylation. Heating phenyl salicylate in turn gives xanthone
Xanthone is an organic compound with the molecular formula O 6H4CO. It is a white solid.
In 1939, xanthone was introduced as an insecticide and it currently finds uses as Insecticide, ovicide for codling moth eggs and as a larvicide. Xanthone ...
.
:2C6H5O2C6H4OH → 2C6H5OH + O 6H4">6H4sub>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
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...
''o''-salicylotoluide. Salicylamide
Salicylamide (''o''-hydroxybenzamide or amide of salicyl) is a non-prescription drug with analgesic and antipyretic properties. Its medicinal uses are similar to those of aspirin. Salicylamide is used in combination with both aspirin and caffe ...
s are a type of drug.
Medical
It has been used as an antiseptic
An antiseptic (from Greek ἀντί ''anti'', "against" and σηπτικός ''sēptikos'', "putrefactive") is an antimicrobial substance or compound that is applied to living tissue/skin to reduce the possibility of infection, sepsis, or putre ...
based on the antibacterial activity upon hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
in the small intestine.
It acts as a mild analgesic
An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...
.
History
The Swiss physician Hermann Sahli Hermann Sahli (May 23, 1856 – April 28, 1933) was a Swiss internist who was a native of Bern.
In 1878 he earned his doctorate from the University of Bern, and subsequently became an assistant to Ludwig Lichtheim (1845–1915) in Bern. Afte ...
(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
Wilhelm Marceli Nencki (15 January 1847 in Boczki, Zduńska Wola County – 14 October 1901 in Saint Petersburg) was a Polish chemist and doctor.
Work
Nencki's main scientific interest concentrated on urea synthesis, the chemistry of purines a ...
of Bern
german: Berner(in)french: Bernois(e) it, bernese
, neighboring_municipalities = Bremgarten bei Bern, Frauenkappelen, Ittigen, Kirchlindach, Köniz, Mühleberg, Muri bei Bern, Neuenegg, Ostermundigen, Wohlen bei Bern, Zollikofen
, website ...
, Switzerland, if he knew of a salicylate compound that lacked sodium salicylate's side effects. Nencki recommended phenyl salicylate, which he had synthesized circa 1883. While Nencki had been investigating how phenyl salicylate behaved in the body, he hadn't published his findings. Meanwhile, the German chemist Richard Seifert ( de) (1861–1919), a student of the German chemist Rudolf Wilhelm Schmitt ( de) (1830–1898), independently synthesized phenyl salicylate in 1885. In 1885, Seifert accepted a position at the Heyden chemical corporation ( de) of Radebeul
Radebeul ( hsb, Radobyle) is a town (''große Kreisstadt'') in the Elbe valley in the district of Meißen in Saxony, Germany, a suburb of Dresden. It is well known for its viticulture, a museum dedicated to writer Karl May, and a narrow gaug ...
, Germany, which manufactured salicylic acid. The United States granted to Nencki and Seifert a patent for the production of phenyl salicylate,[Nencki, Marrel V. ; Seifert, Richar]
"Production of salol"
U.S. Patent no. 350,012 (filed: 22 July 1886 ; issued: 28 September 1886). whereas Germany granted a patent for its production to Nencki and the Heyden corporation. The Heyden company subsequently sold phenyl salicylate as a pharmaceutical, under the commercial name "Salol", a contraction of "SALicylate of phenOL". Among other applications, Salol was used as an orally administered antiseptic for the small intestine, where the compound is hydrolyzed
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.
Biological hydrolysis ...
into salicylic acid and phenol.
See also
Phenyl salicylate is used in school laboratory demonstrations on how cooling rates affect crystal size in igneous rock
Igneous rock (derived from the Latin word ''ignis'' meaning fire), or magmatic rock, is one of the three main The three types of rocks, rock types, the others being Sedimentary rock, sedimentary and metamorphic rock, metamorphic. Igneous rock ...
s, and can be used to demonstrate seed crystal selectiveness.
References
{{Urologicals, including antispasmodics
Phenol esters
Salicylate esters
1886 introductions
3-Hydroxypropenals