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Salicin

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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.

Medicinal aspects

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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]

References

[edit]
Look up salicin in Wiktionary, the free dictionary.
  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. ^ a b 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.
  5. ^ "Salicin". Stanford Chemicals. Retrieved Oct 21, 2024.
  6. ^ "History of Aspirin". About.com Inventors. Archived from the original on July 20, 2012. Retrieved 2016-06-15.
  7. ^ Daniells, S (2006-10-09). "Symrise explores cheaper alternatives in bitter-maskers". www.foodnavigator.com. Retrieved 2007-12-13.
  8. ^ "Willow bark | University of Maryland Medical Center". Archived from the original on 2013-10-30. Retrieved 2013-10-21.
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