Salicyl alcohol

Last updated
Salicyl alcohol
Salicyl alcohol.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-960-5
PubChem CID
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:
GHS-pictogram-exclam.svg
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).

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]

Contents

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

Related Research Articles

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Salicylic acid is an organic compound with the formula HOC6H4COOH. 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 Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen. The name is from Latin salix for willow tree, from which it was initially identified and derived. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates.

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References

  1. "2-Hydroxybenzyl alcohol". chemicalbook.com.
  2. 1 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) 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.