Phenyl salicylate, or salol, is the
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
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 (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 HOC6H4COOH. A colorless (or white), bitter-tasting solid, it is a precursor to and a active metabolite, metabolite of acetylsalicylic acid (aspirin). It is a plant hormone, and has been lis ...
with phenol
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire.
The molecule consists of a phenyl group () ...
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 C13H8O2. It is a white solid.
In 1939, xanthone was introduced as an insecticide and it currently finds uses as ovicide for codling moth eggs and as a larvicide. Xanthone is also use ...
.
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 chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...
''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 caffei ...
s are a type of drug.
Medical
It has been used as an antiseptic
An antiseptic ( and ) is an antimicrobial substance or compound that is applied to living tissue to reduce the possibility of sepsis, infection, or putrefaction. Antiseptics are generally distinguished from ''antibiotics'' by the latter's abil ...
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, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in s ...
.
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. Afterwa ...
(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
Bern (), or Berne (), ; ; ; . is the ''de facto'' Capital city, capital of Switzerland, referred to as the "federal city".; ; ; . According to the Swiss constitution, the Swiss Confederation intentionally has no "capital", but Bern has gov ...
, 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 (; ) is a town (''große Kreisstadt'') in the Elbe valley in the district of Meißen (district), Meißen in Saxony, Germany, a suburb of Dresden. It is well known for its viticulture, a Karl May Museum, museum dedicated to writer Karl ...
, 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,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 hydrolysi ...
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 ( ), or magmatic rock, is one of the three main rock types, the others being sedimentary and metamorphic. Igneous rocks are formed through the cooling and solidification of magma or lava.
The magma can be derived from partial ...
s, and can be used to demonstrate seed crystal
A seed crystal is a small piece of single crystal or polycrystal material from which a large crystal of typically the same material is grown in a laboratory. Used to replicate material, the use of seed crystal to promote growth avoids the otherwi ...
selectiveness.
References
{{Urologicals, including antispasmodics
Phenol esters
Salicylate esters
1886 introductions
3-Hydroxypropenals
Substances discovered in the 19th century