Salicin

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 ;
3D model (JSmol)	Interactive image;
Abbreviations	Glc(b)-O-Ph(2-CH2OH)
ChemSpider	388601 ;
ECHA InfoCard	100.004.847
KEGG	C01451 ;
PubChem CID	439503;
RTECS number	LZ5901700;
UNII	4649620TBZ ;
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
Melting point	207 °C (405 °F; 480 K)
Boiling point	240 decomp.
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
	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). verify (what is ?) Infobox references

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

^ Merck Index, 11th Edition, 8293
^ ^a ^b ^c Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.312. ISBN 9781498754293.
^ PubChem
^ Pasteels, J. M.; Rowell-Rahier, M.; Braekman, J. C.; Dupont, A. (1983). "Salicin from host plant as precursor of salicylaldehyde in defensive secretion of Chrysomeline larvae". Physiological Entomology. 8 (3): 307–314. doi:10.1111/j.1365-3032.1983.tb00362.x. S2CID 85066862.

[1] Merck Index, 11th Edition, 8293

[crc-2] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.312. ISBN 9781498754293.

[PubChemSafety-3] PubChem

[4] Pasteels, J. M.; Rowell-Rahier, M.; Braekman, J. C.; Dupont, A. (1983). "Salicin from host plant as precursor of salicylaldehyde in defensive secretion of Chrysomeline larvae". Physiological Entomology. 8 (3): 307–314. doi:10.1111/j.1365-3032.1983.tb00362.x. S2CID 85066862.

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