Salicyl alcohol
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Names | |
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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]
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.001.782 ![]() |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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 pictograms | ![]() |
GHS Signal word | Warning |
GHS hazard statements
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H315, H319, H335 |
P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, 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 C6H4(OH)(CH2OH). It is a white solid that is used as a precursor in organic synthesis.[3]
Chemical synthesis[]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/4/47/Reduction_of_salicylaldehyde_with_LAH.png/220px-Reduction_of_salicylaldehyde_with_LAH.png)
Reaction scheme for the reduction of salicylaldehyde to salicyl alcohol via lithium aluminium hydride.
Salicyl alcohol can be prepared through the reduction of salicylaldehyde via lithium aluminium hydride (LAH) in THF.[citation needed]
Applications[]
Chemical sweeteners were formed by acetal formation with e.g. isovanillin (Cmp4).[4]
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.[5] 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[]
- ^ "2-Hydroxybenzyl alcohol". chemicalbook.com.
- ^ Jump up to: 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.CS1 maint: multiple names: authors list (link)
- ^ 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.
- ^ 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.
Categories:
- Primary alcohols
- Phenols
- Alcohol stubs