Salicin
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| General | |||||||||||||||||||
| Surname | Salicin | ||||||||||||||||||
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| Molecular formula | C 13 H 18 O 7 | ||||||||||||||||||
| Brief description |
colorless solid |
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| properties | |||||||||||||||||||
| Molar mass | 286.28 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
196-202 ° C |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Salicin is a glucoside in which salicyl alcohol ( saligenin ) is β-glycosidically bound to glucose . In 1828 it was first isolated from the bark of willows by Johann Andreas Buchner (and at about the same time by the pharmacist Pierre-Joseph Leroux (1795–1870)), who gave this compound its name, derived from the Latin word salix for willow.
Natural occurrence
Salicin and other derivatives of salicylic acid occur naturally in willows (e.g. white willow ), in the herb of the wild pansy ( Viola tricolor ), in real meadowsweet ( Filipendula ulmaria , formerly: Spiraea ulmaria ), in the shamberry ( Gaultheria procumbens ) as well as in poplar trees ( Populus alba , P. candicans , P. nigra and P. tremula ).
Extraction
Salicin is isolated from plants (mainly from the willow bark) .
Pharmacological effect
Salicyl alcohol glycosides (such as salicin, salireposid, salicortin, fragilin, picein and others) are split in the intestine to glucose and the aglycon salicyl alcohol, which is then oxidatively converted in the liver to salicylic acid (2-hydroxybenzoic acid). Salicylic acid inhibits the synthesis of prostaglandins by blocking the enzyme cyclooxygenase (COX) and thus has an analgesic effect, among other things . However, a three-arm study with daily intake of willow bark extract with salicin (240 mg / d) showed a significantly lower effect on platelet aggregation than acetylsalicylic acid (100 mg / d) .
Web links
- Natural substance wiki: Salicin
- P. Marson and G. Pansero. The Italian contributions to the history of salicylates . In: Reumatismo . 2006 Jan-Mar; 58 (1): 66-75
literature
- B. Schmid, I. Kötter, L. Heide: Pharmacokinetics of salicin after oral administration of a standardized willow bark extract . In: European Journal of Clinical Pharmacology . tape 57 , no. 5 , August 2001, p. 387-391 , doi : 10.1007 / s002280100325 .
- Claudia Biegert, Irmela Wagner, Rainer Lüdtke, Ina Kötter, Claudia Lohmüller, Ilhan Günaydin, Katja Taxis, Lutz Heide: Efficacy and safety of willow bark extract in the treatment of osteoarthritis and rheumatoid arthritis: results of 2 randomized double-controlled blind trials. In: The Journal of Rheumatology . tape 31 , no. November 11 , 2004, pp. 2121-2130 , PMID 15517622 .
Individual evidence
- ↑ entry to salicin in CosIng database of the European Commission, accessed on 22 July 2020th
- ↑ a b c d Data sheet D - (-) - Salicin from Sigma-Aldrich , accessed on November 8, 2016 ( PDF ).
- ↑ Derek Lowe, Das Chemiebuch, Librero 2017, p. 216
- ↑ a b R. Hansel, O. Sticher (Ed.): Pharmakognosie - Phytopharmazie . 9., revised. and updated edition. Springer, Heidelberg 2010, ISBN 978-3-642-00962-4 , pp. 155 .
- ↑ N. Krivoy, E. Pavlotzky, S. Chrubasik, E. Eisenberg, G. Brook: Effect of salicis cortex extract on human platelet aggregation. In: Planta Medica. Volume 67, No. 3, Georg Thieme Stuttgart, April 2001, pp. 209-212; doi: 10.1055 / s-2001-12000 , PMID 11345689 .