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Salicin

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Salicin[1]
Names
Preferred 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
ECHA InfoCard 100.004.847 Edit this at Wikidata
KEGG
RTECS number
  • LZ5901700
UNII
  • InChI=1/C13H18O7/c14/h1-4,9-18H,5-6H2
Properties
C13H18O7
Molar mass 286.280 g·mol−1
Appearance White crystals
Melting point 197 to 200 °C (387 to 392 °F; 470 to 473 K)
4.3 g/100 mL
Solubility in Ethanol 0.3g/100 mL
Solubility in DMSO 2 g/100mL
Solubility in dimethyl formamide 3 g/100mL
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Skin sensitizer / Contact dermatitis[2]
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.[3]

Medicinal aspects

Salicin is found in the bark of and leaves of willows, poplars and various other plants. Derivates are found in castoreum. Salicin from meadowsweet was used in the synthesis of aspirin (acetylsalicylic acid),[4] in 1899 by scientists at Bayer. Salicin tastes bitter like quinine.[5]

Salicin may cause an allergic skin reaction (skin sensitization; category 1).[2]

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.[6]

References

  1. ^ Merck Index, 11th Edition, 8293
  2. ^ a b PubChem
  3. ^ 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.
  4. ^ "History of Aspirin". About.com Inventors. Retrieved 2016-06-15.
  5. ^ Daniells, S (2006-10-09). "Symrise explores cheaper alternatives in bitter-maskers". www.foodnavigator.com. Retrieved 2007-12-13.
  6. ^ "Willow bark | University of Maryland Medical Center". Archived from the original on 2013-10-30. Retrieved 2013-10-21.
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