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. The ...

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 oil ...

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 Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...

Applications

Chemical sweeteners were formed by acetal formation with ''e.g.''

isovanillin Isovanillin is a phenolic aldehyde, an organic compound and isomer of vanillin. It is a selective inhibitor of aldehyde oxidase. It is not a substrate of that enzyme, and is metabolized by aldehyde dehydrogenase into isovanillic acid, which co ...

(Cmp4). Salicyl alcohol appears as a

pharmacophore 300px, An example of a pharmacophore model. A pharmacophore is an abstract description of molecular features that are necessary for molecular recognition of a ligand by a biological macromolecule. IUPAC defines a pharmacophore to be "an ensemble o ...

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
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o
CID:154236944

Biosynthesis

Salicyl alcohol is the

precursor Precursor or Precursors may refer to: * Precursor (religion), a forerunner, predecessor ** The Precursor, John the Baptist Science and technology * Precursor (bird), a hypothesized genus of fossil birds that was composed of fossilized parts of u ...

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 ...

. 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 va ...

enzymatic Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. ...

hydrolysis by

Salicyl-alcohol beta-D-glucosyltransferase In enzymology, a salicyl-alcohol beta-D-glucosyltransferase () is an enzyme that catalyzes the chemical reaction :UDP-glucose + salicyl alcohol \rightleftharpoons UDP + salicin Thus, the two substrates of this enzyme are UDP-glucose and salic ...

or by

acid hydrolysis In organic chemistry, acid hydrolysis is a hydrolysis process in which a protic acid is used to catalyze the cleavage of a chemical bond via a nucleophilic substitution reaction, with the addition of the elements of water (H2O). For example, in th ...

References

Primary alcohols Phenols {{alcohol-stub

Chemical synthesis

Applications

Biosynthesis

See also

References