Salicin

Salicin

Names
IUPAC name (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3, 4,5-triol
Other names Salicin; D-(−)-Salicin; Salicoside; 2-(Hydroxymethyl)phenyl -β-D-glucopyranoside
Identifiers
CAS Number	138-52-3 Y
3D model (JSmol)	Interactive image
ChemSpider	388601 N
ECHA InfoCard	100.004.847
KEGG	C01451 N
PubChem CID	439503
RTECS number	LZ5901700
UNII	4649620TBZ Y
CompTox Dashboard (EPA)	DTXSID10883326
InChI InChI=1/C13H18O7/c14/h1-4,9-18H,5-6H2
SMILES c1ccc(c(c1)CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Properties
Chemical formula	C13H18O7
Molar mass	286.280 g·mol−1
Melting point	197 to 200 °C (387 to 392 °F; 470 to 473 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Salicin is an alcoholic β-glucoside. Salicin is produced in (and named after) willow (Salix) bark and acts as an anti-inflammatory agent in the human body. Salicin is also commonly found in the bark of Populus species, and the leaves of willows and poplars. It is also found in castoreum, which was used as an analgesic, anti-inflammatory, and antipyretic. The activity of castoreum has been credited to the accumulation of salicin from willow trees in the beaver's diet, which is transformed to salicylic acid and has an action very similar to aspirin. Salicin was the historical origin of aspirin and is chemically related to it. When consumed, the acetalic ether bridge is broken down. The two parts of the molecule, glucose and salicyl alcohol, then are metabolized separately. By oxidizing the alcohol function the aromatic part finally is metabolized to salicylic acid. Salicin tastes bitter like quinine.

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.