Salicin

Salicin^[1]

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
ChemSpider	388601 N
Jmol interactive 3D	Image
KEGG	C01451 N
PubChem	439503
RTECS number	LZ5901700
UNII	4649620TBZ Y
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	286.28 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 an anti-inflammatory agent that is produced in (and named after) willow (Salix) bark.^[2] 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.^[3] Salicin is closely related in chemical make-up to aspirin. 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 elicits bitterness like quinine, when consumed.^[4] Alkaline cleavage of the glucoside populin produces benzoate and salicin.^[5]

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, similar to reactions to aspirin. Others that are advised against taking salicin are those with asthma, diabetes, gout, gastritis, hemophilia, stomach ulcers, children under 16, pregnant and breastfeeding women.^[6][7]

References