Salicyl alcohol

In the following article we are going to delve into the exciting world of Salicyl alcohol, exploring its most relevant aspects and its implications in modern society. From its emergence to its effects on an individual and collective level, we will embark on a journey of discovery and reflection that will allow us to better understand Salicyl alcohol and its impact on our daily lives. Through in-depth analysis and case studies, we will seek to shed light on the lesser-known aspects of Salicyl alcohol and its relevance in the contemporary world. Join us on this journey of knowledge and discovery, where we hope to open perspectives and generate reflections around 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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.782 Edit this at Wikidata
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 , 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]

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

References

  1. ^ "2-Hydroxybenzyl alcohol". chemicalbook.com.
  2. ^ a b "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.