R,3 S,4 S,5 R,6 S)-2-(Hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3, 4,5-triol
D-(−)-Salicin; Salicoside; 2-(Hydroxymethyl)phenyl
RTECS number LZ5901700
13H 18O 7
Molar mass 286.28 g·mol
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
(at 25 °C [77 °F], 100 kPa).
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Salicin is an alcoholic β- glucoside. Salicin is an anti-inflammatory agent that is produced in willow bark. Salicin is also commonly found in the bark of Populus species, and the leaves of willows and poplars. It is also found in [2 ] 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. Salicin is closely related in chemical make-up to [3 ] aspirin. When consumed, the acetalic ether bridge is broken down. The two parts of the molecule, glucose and salicylic alcohol, then are metabolized separately. By oxidizing the alcohol function the aromatic part finally is metabolized to salicylic acid. Salicin elicits bitterness like quinine, when consumed. [4 ] Alkaline cleavage of the glucoside populin produces benzoate and salicin. [5 ]
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, stomach causing ulcers, diarrhea, bleeding or digestive discomfort. Some people may be allergic, or sensitive to salicylates, similar to reactions to aspirin. Others that are advised against taking salicin are those with asthma, diabetes, gout, gastritis, hemophilia, stomach ulcers, children under 16, pregnant and breastfeeding women.
[6 ] [7 ]
References [ edit ]
^ , 11th Edition, 8293 Merck Index
^ 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
^ Stephen Pincock (28 March 2005). "The quest for pain relief: how much have we improved on the past?" . Retrieved . 2007-06-17
^ Daniells, S (09/10/2006). "Symrise explores cheaper alternatives in bitter-maskers". www.foodnavigator.com . Retrieved . 2007-12-13
^ 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.