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Salicyl alcohol - Wikipedia

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From Wikipedia, the free encyclopedia

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

Chemical compound

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[edit]

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.

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.

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

^ "2-Hydroxybenzyl alcohol". chemicalbook.com.
^ ^a ^b "salicylic alcohol". chemspider.com.
^ 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)
^ Maliverney, Christian; Mulhauser, Michel (2000). "Hydroxybenzaldehydes". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0825041813011209.a01. ISBN 978-0-471-48494-3.
^ 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.
^ 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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