salicyl alcohol
{{chembox
| Name = Salicyl alcohol
| ImageFile = Salicyl alcohol.svg
| PIN = 2-(Hydroxymethyl)phenol
| OtherNames = 2-Hydroxybenzyl alcohol, Salicain, Diathesin, Saligenin, Saligenol, Salicyl alcohol, α,2-Toluenediol, o-Methylolphenol, 2-Methylolphenol, Salicylic alcohol{{cite web|url=http://www.chemicalbook.com/ChemicalProductProperty_EN_CB9303076.htm|title=2-Hydroxybenzyl alcohol|work=chemicalbook.com}}
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 90-01-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FA1N0842KB
| ChEMBL_Ref =
| ChEMBL =
| ChemSpiderID_Ref =
| ChemSpiderID = 4962
| ChEBI_Ref =
| ChEBI =
| DrugBank_Ref =
| DrugBank =
| EINECS = 201-960-5
| KEGG_Ref =
| KEGG =
| PubChem = 5146
| SMILES = c1ccc(c(c1)CO)O
| StdInChI_Ref =
| StdInChI = InChI=1S/C7H8O2/c8-5-6-3-1-2-4-7(6)9/h1-4,8-9H,5H2
| StdInChIKey_Ref =
| StdInChIKey = CQRYARSYNCAZFO-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=7 | H=8 | O=2
| Density = 1.16 g/cm3
| MeltingPtC = 86
| BoilingPtC = 267
| Solubility = 67g/L at 22 °C{{cite web|url=http://www.chemspider.com/Chemical-Structure.4962.html|title=salicylic alcohol|work=chemspider.com}}
| MagSus = −76.9·10−6 cm3/mol
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|H315|319|335}}
| PPhrases = {{P-phrases|P261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
}}
}}
Salicyl alcohol (saligenin) is an organic compound with the formula {{chem2|C6HOH(CH2OH}}. It is a white solid that is used as a precursor in organic synthesis.{{cite journal |doi=10.15227/orgsyn.081.0171|title=Synthesis of 9-Spiroepoxy-endo-Tricyclo[5.2.2.0]undeca-4,10-dien-8-one|journal=Organic Syntheses|year=2005|volume=81|page=171|author=Vishwakarma Singh, Mini Porinchu, Punitha Vedantham, Pramod K. Sahu1|doi-access=free}}
Synthesis and applications
Salicyl alcohol is produced by the hydroxymethylation of phenol using formaldehyde:{{cite book |doi=10.1002/0471238961.0825041813011209.a01 |chapter=Hydroxybenzaldehydes |title=Kirk-Othmer Encyclopedia of Chemical Technology |date=2000 |last1=Maliverney |first1=Christian |last2=Mulhauser |first2=Michel |isbn=978-0-471-48494-3 }}
:{{chem2|C6H5OH + CH2O -> C6H4OH(CH2OH}}
Air oxidation of salicyl alcohol gives salicylaldehyde.
:{{chem2|C6H4OH(CH2OH + O -> C6H4OH(CHO) +H2O}}
Chemical sweeteners are formed by acetal formation with e.g. isovanillin (Cmp4).{{cite journal|last1=Bassoli|first1=Angela|last2=Merlini|first2=Lucio|last3=Morini|first3=Gabriella|title=Isovanillyl sweeteners. From molecules to receptors|journal=Pure and Applied Chemistry|volume=74|issue=7|year=2002|pages=1181–1187|issn=1365-3075|doi=10.1351/pac200274071181|s2cid=53554546|doi-access=free}}
Salicyl alcohol appears as a pharmacophore in several notable β2-adrenoceptor agonists (e.g. salbutamol), as well as in synthetic estrone analogs, e.g. [https://pubchem.ncbi.nlm.nih.gov/compound/22940780 CID:22940780] or [https://pubchem.ncbi.nlm.nih.gov/compound/154236944 CID:154236944].
Biosynthesis
Salicyl alcohol is the precursor of salicylic acid.{{cite journal |doi=10.1016/j.jbiotec.2004.10.013|title=Enzymatic synthesis and anti-coagulant effect of salicin analogs by using the Leuconostoc mesenteroides glucansucrase acceptor reaction|year=2005|last1=Seo|first1=Eun-Seong|last2=Lee|first2=Jin-Ha|last3=Park|first3=Ji-Young|last4=Kim|first4=Doman|last5=Han|first5=Ho-Jae|last6=Robyt|first6=John F.|journal=Journal of Biotechnology|volume=117|issue=1|pages=31–38|pmid=15831245}} 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