Salicyl alcohol

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]

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

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