Salicyl alcohol (saligenin) is an organic compound with the formula C6HOH(CH2OH. It is a white solid that is used as a precursor in organic synthesis.[3]

Synthesis and applications

Salicyl alcohol is produced by the hydroxymethylation of phenol using formaldehyde:[4]

C6H5OH + CH2O → C6H4OH(CH2OH

Air oxidation of salicyl alcohol gives salicylaldehyde.

C6H4OH(CH2OH + O → C6H4OH(CHO) +H2O

Chemical sweeteners are formed by acetal formation with e.g. isovanillin (Cmp4).[5]

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.[6] It is formed from salicin by enzymatic hydrolysis by Salicyl-alcohol beta-D-glucosyltransferase or by acid hydrolysis.

See also

References

  1. ^ "2-Hydroxybenzyl alcohol". chemicalbook.com.
  2. ^ a b "salicylic alcohol". chemspider.com.
  3. ^ Vishwakarma Singh, Mini Porinchu, Punitha Vedantham, Pramod K. Sahu1 (2005). "Synthesis of 9-Spiroepoxy-endo-Tricyclo[5.2.2.0]undeca-4,10-dien-8-one". Organic Syntheses. 81: 171. doi:10.15227/orgsyn.081.0171.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  4. ^ Maliverney, Christian; Mulhauser, Michel (2000). "Hydroxybenzaldehydes". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0825041813011209.a01. ISBN 978-0-471-48494-3.
  5. ^ Bassoli, Angela; Merlini, Lucio; Morini, Gabriella (2002). "Isovanillyl sweeteners. From molecules to receptors". Pure and Applied Chemistry. 74 (7): 1181–1187. doi:10.1351/pac200274071181. ISSN 1365-3075. S2CID 53554546.
  6. ^ Seo, Eun-Seong; Lee, Jin-Ha; Park, Ji-Young; Kim, Doman; Han, Ho-Jae; Robyt, John F. (2005). "Enzymatic synthesis and anti-coagulant effect of salicin analogs by using the Leuconostoc mesenteroides glucansucrase acceptor reaction". Journal of Biotechnology. 117 (1): 31–38. doi:10.1016/j.jbiotec.2004.10.013. PMID 15831245.