Salicyl alcohol

Salicyl alcohol (saligenin) is an organic compound with the formula C6H4(OH)(CH2OH). It is a white solid that is used as a precursor in organic synthesis.[3]

Salicyl alcohol
Names
Preferred IUPAC name
2-(Hydroxymethyl)phenol
Other names
2-Hydroxybenzyl alcohol, Salicain, Diathesin, Saligenin, Saligenol, Salicyl alcohol, α,2-Toluenediol, o-Methylolphenol, 2-Methylolphenol, Salicylic alcohol[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.782
EC Number
  • 201-960-5
UNII
  • InChI=1S/C7H8O2/c8-5-6-3-1-2-4-7(6)9/h1-4,8-9H,5H2
    Key: CQRYARSYNCAZFO-UHFFFAOYSA-N
  • c1ccc(c(c1)CO)O
Properties
C7H8O2
Molar mass 124.139 g·mol−1
Density 1.16 g/cm3
Melting point 86 °C (187 °F; 359 K)
Boiling point 267 °C (513 °F; 540 K)
67g/L at 22 °C[2]
-76.9·10−6 cm3/mol
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 134 °C[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Chemical synthesis
Reaction scheme for the reduction of salicylaldehyde to salicyl alcohol via lithium aluminium hydride.

Salicyl alcohol can be prepared through the reduction of salicylaldehyde via lithium aluminium hydride (LAH) in THF.


Applications

Chemical sweeteners were formed by acetal formation with e.g. isovanillin (Cmp4).[4]

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.[5] 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. "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)
  4. 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.
  5. 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.


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