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Salicyl alcohol (saligenin) is an
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. Th ...
with the formula C6H4(OH)(CH2OH). It is a white solid that is used as a precursor in
organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
.


Chemical synthesis

Salicyl alcohol can be prepared through the reduction of
salicylaldehyde Salicylic aldehyde (2-hydroxybenzaldehyde) is the organic compound with the formula (C7 H6 O2) C6H4CHO-2-OH. Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oi ...
via
lithium aluminium hydride Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li Al H4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic ...
(LAH) in THF.


Applications

Chemical sweeteners were formed by acetal formation with ''e.g.'' isovanillin (Cmp4). Salicyl alcohol appears as a pharmacophore in several notable β2-adrenoceptor agonists (e.g.
salbutamol Salbutamol, also known as albuterol and sold under the brand name Ventolin among others, is a medication that opens up the medium and large airways in the lungs. It is a short-acting β2 adrenergic receptor agonist which works by causing rel ...
), as well as in synthetic
estrone Estrone (E1), also spelled oestrone, is a steroid, a weak estrogen, and a minor female sex hormone. It is one of three major endogenous estrogens, the others being estradiol and estriol. Estrone, as well as the other estrogens, are synthesized ...
analogs, e.g
CID:22940780
o
CID:154236944


Biosynthesis

Salicyl alcohol is the precursor of
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 Substanc ...
. It is formed from
salicin Salicin is an alcoholic β- glucoside. Salicin is produced in (and named after) willow (''Salix'') bark. It is a biosynthetic precursor to salicylaldehyde. Medicinal aspects Salicin is found in the bark of and leaves of willows, poplars and v ...
by enzymatic hydrolysis by Salicyl-alcohol beta-D-glucosyltransferase or by acid hydrolysis.


See also

* Gastrodigenin (4-hydroxybenzyl alcohol) * Discovery and development of beta2 agonists


References

Primary alcohols Phenols {{alcohol-stub