Salicin

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Salicin[1]
Salicin2DCSDS.svg
Salicin-from-xtal-1984-3D-balls.png
Names
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
138-52-3 YesY
ChemSpider 388601 N
Jmol 3D model Interactive image
KEGG C01451 N
PubChem 439503
RTECS number LZ5901700
UNII 4649620TBZ YesY
Properties
C13H18O7
Molar mass 286.28 g·mol−1
Melting point 197 to 200 °C (387 to 392 °F; 470 to 473 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Salicin is an alcoholic β-glucoside. Salicin is produced in (and named after) willow (Salix) bark and acts as an anti-inflammatory agent in the human body.[2] Salicin is also commonly found in the bark of Populus species, and the leaves of willows and poplars. It is also found in castoreum, which was used as an analgesic, anti-inflammatory, and antipyretic. The activity of castoreum has been credited to the accumulation of salicin from willow trees in the beaver's diet, which is transformed to salicylic acid and has an action very similar to aspirin.[3] Salicin was the historical origin aspirin[4] and is chemically related to it. When consumed, the acetalic ether bridge is broken down. The two parts of the molecule, glucose and salicyl alcohol, then are metabolized separately. By oxidizing the alcohol function the aromatic part finally is metabolized to salicylic acid. Salicin tastes bitter like quinine.[5] Alkaline cleavage of the glucoside populin produces benzoate and salicin.[6]

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.[7][8]

References[edit]

  1. ^ Merck Index, 11th Edition, 8293
  2. ^ Uchytil, RJ (1991). "Salix drummondiana". Fire Effects Information System,. Online. U.S. Department of Agriculture, Forest Service, Rocky Mountain Research Station, Fire Sciences Laboratory (Producer). Retrieved 2006-07-19. 
  3. ^ Stephen Pincock (28 March 2005). "The quest for pain relief: how much have we improved on the past?". Retrieved 2007-06-17. 
  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. ^ Richtmyer, Nelson K.; Yeakel, Eleanor H. (1934). "The Structure of Populin". Journal of the American Chemical Society 56 (11): 2495–2497. doi:10.1021/ja01326a090. ISSN 0002-7863. 
  7. ^ http://umm.edu/health/medical/altmed/herb/willow-bark
  8. ^ http://www.heart-health-guide.com/salicin.html