Syringin
Structural formula | |||||||||||||||||||
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General | |||||||||||||||||||
Surname | Syringin | ||||||||||||||||||
other names |
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Molecular formula | C 17 H 24 O 9 | ||||||||||||||||||
Brief description |
colorless, needle-shaped crystals |
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properties | |||||||||||||||||||
Molar mass | 372.37 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
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Melting point |
192 ° C |
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safety instructions | |||||||||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Syringin is a natural product that occurs in the common lilac ( Syringa vulgaris ) and was first isolated in 1841.
History and occurrence
Alphons Meillet isolated a substance from the bark of the common lilac , which he called lilacin , based on the violet color of the flowers . Franz J. Bernays isolated the substance from leaves and green branches of the same plant and named it syringin based on the Latin name . It is also found as Eleutherosid B in Siberian Ginseng ( Eleutherococcus senticosus ).
properties
Syringin forms colorless, needle-shaped crystals that melt at 192 ° C. From a chemical point of view, it is the glycoside with sinapyl alcohol as aglycon and glucose . Structurally and specifically, the following are derived from it: syringol , syringa alcohol , syringaaldehyde , syringic acid and acetosyringone , structurally also: sinapyl alcohol, sinapinaldehyde and sinapinic acid .
Syringin lowers the glucose concentration in the blood of rats in which diabetes was previously caused by streptozocin .
Individual evidence
- ↑ a b c Merck, without further references (PDF; 338 kB).
- ↑ a b Data sheet Eleutheroside B at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
- ↑ Alphons Meillet: "Lilacin", in: Justus Liebigs Annalen der Chemie , 1841 , 40 (3), pp. 319-320 ( doi : 10.1002 / jlac.18410400342 ).
- ↑ Alphons Meillet: "About the Lilacin, the bitter principle of the Lilas ( Syringa vulgaris )", in: Archiv der Pharmazie , 1842 , 79 (3), pp. 354-356 ( doi : 10.1002 / ardp.18420790312 ).
- ^ Franz J. Bernays: "Ueber das Syringin", in: Pharmaceutisches Central Blatt , 1841 , 12 , pp. 938-939 ( limited preview in Google book search).
- ↑ Franz J. Bernays: "About a new crystallizable plant substance, the syringin from Syringa vulgaris", in: Repertorium für die Pharmacie , 1841 , 74 , pp. 348-351 ( restricted preview in the Google book search).
- ↑ Ho-Shan Niu, I-Min Liu, Juei-Tang Cheng, Che-Ling Lin, Feng-Lin Hsu: "Hypoglycemic Effect of Syringin from Eleutherococcus senticosus in Streptozotocin-Induced Diabetic Rats", in: Planta Medica , 2008 , 74 , Pp. 109-113 ( doi : 10.1055 / s-2008-1034275 ).