Structure via PubChem · Public domain (PubChem)
D-(−)-salicin
Sign in to saveAlso known as saligenin beta-D-glucopyranoside, o-(hydroxymethyl)phenyl beta-D-glucopyranoside, salicyl alcohol glucoside, D-(-)-salicin, 2-(hydroxymethyl)phenyl-O-beta-D-glucopyranoside, 2-(hydroxymethyl)phenyl-beta-D-glucopyranoside, (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol, (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]tetrahydropyran-3,4,5-triol
Salicin is an alcoholic β-glucoside. Salicin is produced in (and named after) willow (Salix) bark. It is a biosynthetic precursor to salicylaldehyde.
Chemical data
- Formula
- C13H18O7
- Molecular weight
- 286.28 g/mol
- IUPAC name
- (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
- SMILES
- C1=CC=C(C(=C1)CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
- InChIKey
- NGFMICBWJRZIBI-UJPOAAIJSA-N
- XLogP
- -1.2
- Polar surface area
- 120 Ų
- H-bond donors
- 5
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
18 papers- D(-)-Salicin inhibits the LPS-induced inflammation in RAW264.7 cells and mouse models.International immunopharmacology · 2015
- D(-)-salicin inhibits RANKL-induced osteoclast differentiation and function in vitro.Fitoterapia · 2022
- Biosynthesis and metabolism of β-d-salicin: A novel molecule that exerts biological function in humans and plants.Biotechnology reports (Amsterdam, Netherlands) · 2014
- Relaxation behaviour of D(-)-salicin as studied by Thermally Stimulated Depolarisation Currents (TSDC) and Differential Scanning Calorimetry (DSC).International journal of pharmaceutics · 2008
- Miktoarm star copolymers from D-(-)-salicin core aggregated into dandelion-like structures as anticancer drug delivery systems: synthesis, self-assembly and drug release.International journal of pharmaceutics · 2016
via PubMed
Wikidata facts
- Subclass of
- aromatic alcohol
- Mass
- 286.105
- Image
- Salicin powder crop.jpg
Show 8 more facts
- found in taxon
- Populus alba
- chemical formula
- C₁₃H₁₈O₇
- isomeric SMILES
- C1=CC=C(C(=C1)CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
- canonical SMILES
- C1=CC=C(C(=C1)CO)OC2C(C(C(C(O2)CO)O)O)O
- Commons category
- Salicin
- melting point
- 199
- has characteristic
- bitterness
- described by source
- Encyclopædia Britannica 11th edition
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Medicinal aspects
- References
Salicin is an alcoholic β-glucoside. Salicin is produced in (and named after) willow (Salix) bark. It is a biosynthetic precursor to salicylaldehyde.
Salicin hydrolyses into β-d-glucose and salicyl alcohol (saligenin). Salicyl alcohol can be oxidized into salicylaldehyde and salicylate, both biologically and industrially.
Excerpted from Wikipedia’s “D-(−)-salicin” article, available under the CC BY-SA 4.0 licence.