Salicin

Salicin is an alcoholic β-glucoside. Salicin is produced in (and named after) willow (Salix) bark. It is a biosynthetic precursor to salicylaldehyde.^[4]

Salicin^[1]

Names
IUPAC name 2-(Hydroxymethyl)phenyl β-D-glucopyranoside
Systematic IUPAC name (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
Other names Salicin; D-(−)-Salicin; Salicoside
Identifiers
CAS Number	138-52-3 Y
3D model (JSmol)	Interactive image
Abbreviations	Glc(b)-O-Ph(2-CH2OH)
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 OCc1ccccc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Properties
Chemical formula	C13H18O7
Molar mass	286.280 g·mol−1
Appearance	White crystals
Density	1.434 g/cm3[2]
Melting point	207 °C (405 °F; 480 K)[2]
Boiling point	240 decomp.[2]
Solubility in water	43 g/L
Solubility in Ethanol	3 g/L
Solubility in DMSO	20 g/L
Solubility in dimethyl formamide	30 g/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Skin sensitizer / Contact dermatitis[3]
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H317
Precautionary statements	P261, P272, P280, P302+P352, P333+P313, P362, P363, P501
NFPA 704 (fire diamond)	1 0 0
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 hydrolyses into 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 willows, poplars and various other plants.^[5] Derivates are found in castoreum. Salicin from meadowsweet was used in the synthesis of aspirin (acetylsalicylic acid),^[6] in 1899 by scientists at Bayer. Salicin tastes bitter like quinine.^[7]

Salicin may cause an allergic skin reaction (skin sensitization; category 1).^[3]

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.^[8]