Salicyl alcohol explained

Salicyl alcohol (saligenin) is an organic compound with the formula . It is a white solid that is used as a precursor in organic synthesis.^[1]

Synthesis and applications

Salicyl alcohol is produced by the hydroxymethylation of phenol using formaldehyde:^[2]

Air oxidation of salicyl alcohol gives salicylaldehyde.

Chemical sweeteners are formed by acetal formation with e.g. isovanillin (Cmp4).^[3]

Salicyl alcohol appears as a pharmacophore in several notable β2-adrenoceptor agonists (e.g. salbutamol), as well as in synthetic estrone analogs, e.g. CID:22940780 or CID:154236944.

Biosynthesis

Salicyl alcohol is the precursor of salicylic acid.^[4] It is formed from salicin 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

Notes and References

1. 10.15227/orgsyn.081.0171. Synthesis of 9-Spiroepoxy-endo-Tricyclo[5.2.2.0]undeca-4,10-dien-8-one. Organic Syntheses. 2005. 81. 171. Vishwakarma Singh, Mini Porinchu, Punitha Vedantham, Pramod K. Sahu1. free.
2. Book: 10.1002/0471238961.0825041813011209.a01 . Hydroxybenzaldehydes . Kirk-Othmer Encyclopedia of Chemical Technology . 2000 . Maliverney . Christian . Mulhauser . Michel . 978-0-471-48494-3 .
3. Bassoli. Angela. Merlini. Lucio. Morini. Gabriella. Isovanillyl sweeteners. From molecules to receptors. Pure and Applied Chemistry. 74. 7. 2002. 1181–1187. 1365-3075. 10.1351/pac200274071181. 53554546. free.
4. 10.1016/j.jbiotec.2004.10.013. Enzymatic synthesis and anti-coagulant effect of salicin analogs by using the Leuconostoc mesenteroides glucansucrase acceptor reaction. 2005. Seo. Eun-Seong. Lee. Jin-Ha. Park. Ji-Young. Kim. Doman. Han. Ho-Jae. Robyt. John F.. Journal of Biotechnology. 117. 1. 31–38. 15831245.