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
3D model (JSmol)
Abbreviations Glc(b)-O-Ph(2-CH2OH)
ChemSpider
ECHA InfoCard 100.004.847 Edit this at Wikidata
KEGG
RTECS number
  • LZ5901700
UNII
  • InChI=1/C13H18O7/c14/h1-4,9-18H,5-6H2
  • OCc1ccccc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Properties
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]
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:
GHS07: Exclamation mark
Warning
H317
P261, P272, P280, P302+P352, P333+P313, P362, P363, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

  1. ^ Merck Index, 11th Edition, 8293
  2. ^ a b c Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.312. ISBN 9781498754293.
  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.