Salicin: Difference between revisions

{{short description|Chemical compound}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 447460581

| Name =

| ImageFile1 = Salicin powder crop.jpg

| ImageFile2 = Salicin.svg

| IUPACName = 2-(Hydroxymethyl)phenyl β-<small>D</small>-glucopyranoside

| SystematicName = (2''R'',3''S'',4''S'',5''R'',6''S'')-2-(Hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol

| OtherNames = Salicin; <small>D</small>-(−)-Salicin; Salicoside

| Abbreviations = Glc(b)-O-Ph(2-CH2OH)

| CASNo_Ref = {{cascite|correct|CAS}}

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 388601

| SMILES = OCc1ccccc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

| InChI = 1/C13H18O7/c14/h1-4,9-18H,5-6H2

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C01451

}}

| C=13 | H=18 | O=7

| Appearance = White crystals

| Density = 1.434 g/cm³<ref name=crc/>

| MeltingPtC = 207

| MeltingPt_ref = <ref name=crc>{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = [[CRC Handbook of Chemistry and Physics]] | edition = 97th | publisher = [[CRC Press]] | isbn = 9781498754293|page=3.312}}</ref>

| BoilingPt = 240

| BoilingPt_notes = decomp.<ref name=crc/>

| Solubility = 43 g/L

| Solvent1 = Ethanol

| Solubility1 = 3 g/L

| Solvent2 = DMSO

| Solubility2 = 20 g/L

| Solvent3 = dimethyl formamide

| Solubility3 = 30 g/L

| Pregnancy_category =

| Pregnancy_AU =

| Pregnancy_US = }}

| DetonationV =

| MainHazards = [[Skin sensitizer]] / [[Contact dermatitis]]<ref name=PubChemSafety>[https://pubchem.ncbi.nlm.nih.gov/compound/439503#section=Safety-and-Hazards PubChem]</ref>

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|317}}

| PPhrases = {{P-phrases|261|272|280|302+352|333+313|362|363|501}}

| NFPA-H = 1

| NFPA-F = 0

| NFPA-R = 0

| NFPA-S =

| GHS_ref =

| AutoignitionPt =

| OtherFunction =

| OtherFunction_label =

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'''Salicin''' is an alcoholic β-[[glucoside]]. Salicin is produced in (and named after) [[willow]] (''Salix'') bark. It is a biosynthetic precursor to [[salicylaldehyde]].<ref>{{cite journal |doi=10.1111/j.1365-3032.1983.tb00362.x|title=Salicin from host plant as precursor of salicylaldehyde in defensive secretion of Chrysomeline larvae|year=1983|last1=Pasteels|first1=J. M.|last2=Rowell-Rahier|first2=M.|last3=Braekman|first3=J. C.|last4=Dupont|first4=A.|journal=Physiological Entomology|volume=8|issue=3|pages=307–314|s2cid=85066862|url=https://dipot.ulb.ac.be/dspace/bitstream/2013/95098/4/ac2db4af-9a60-4c77-bdb4-6fa9e75d3003.txt}}</ref>

Salicin hydrolyses into [[Glucose|β-d-glucose]] and [[salicyl alcohol]] (saligenin). Salicyl alcohol can be oxidized into salicylaldehyde and salicylate, both biologically and industrially.

==Medicinal aspects==

Salicin is found in the bark of and leaves of [[willow]]s, [[Populus | poplars]] and various other plants. Derivates are found in [[castoreum]]. Salicin from [[Filipendula ulmaria | meadowsweet]] was used in the synthesis of [[aspirin]] (acetylsalicylic acid),<ref>{{Cite web|url=http://inventors.about.com/library/inventors/blaspirin.htm|archive-url=https://archive.today/20120720230829/http://inventors.about.com/library/inventors/blaspirin.htm|url-status=dead|archive-date=July 20, 2012|title=History of Aspirin|website=About.com Inventors|access-date=2016-06-15}}</ref> in 1899 by scientists at [[Bayer]]. Salicin tastes bitter like [[quinine]].<ref>{{cite web

| last = Daniells

| first = S

| title = Symrise explores cheaper alternatives in bitter-maskers

| publisher = www.foodnavigator.com

| date = 2006-10-09

| url = http://www.foodnavigator.com/Science-Nutrition/Symrise-explores-cheaper-alternatives-in-bitter-maskers

| access-date = 2007-12-13}}</ref>

Salicin may cause an allergic skin reaction (skin sensitization; category 1).<ref name=PubChemSafety/>

Mild side effects are standard, with rare occurrences of nausea, vomiting, rash, dizziness and breathing problems. Overdose from high quantities of salicin can be toxic, damaging kidneys, causing stomach ulcers, diarrhea, bleeding or digestive discomfort. Some people may be allergic or sensitive to salicylates and suffer reactions similar to those produced by aspirin. People should not take salicin if they have asthma, diabetes, gout, gastritis, hemophilia, stomach ulcers; also contraindicated are children under 16, and pregnant and breastfeeding women.<ref>{{Cite web |url=http://umm.edu/health/medical/altmed/herb/willow-bark |title=Willow bark &#124; University of Maryland Medical Center |access-date=2013-10-21 |archive-url=https://web.archive.org/web/20131030093857/http://umm.edu/health/medical/altmed/herb/willow-bark |archive-date=2013-10-30 |url-status=dead }}</ref>

== References ==

{{wictionary|salicin}}

{{Analgesics}}

{{Prostanoidergics}}

[[Category:Natural phenols]]

[[Category:Phenol glucosides]]