Salicyl alcohol

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
CAS Number	90-01-7  Y
3D model (JSmol)	Interactive image
ChemSpider	4962
ECHA InfoCard	100.001.782
EC Number	201-960-5
PubChem CID	5146
UNII	FA1N0842KB  Y
CompTox Dashboard (EPA)	DTXSID9045843
InChI InChI=1S/C7H8O2/c8-5-6-3-1-2-4-7(6)9/h1-4,8-9H,5H2 Key: CQRYARSYNCAZFO-UHFFFAOYSA-N
SMILES c1ccc(c(c1)CO)O
Properties
Chemical formula	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)
Solubility in water	67g/L at 22 °C [2]
Magnetic susceptibility (χ)	−76.9·10−6 cm3/mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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

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

• Gastrodigenin (4-hydroxybenzyl alcohol)
• Discovery and development of beta2 agonists

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 .
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.