Syringin

Structural formula
General
Surname	Syringin
other names	4 - [(1 E ) -3-hydroxyprop-1-en-1-yl] -2,6-dimethoxyphenyl β- D -glucopyranoside; Eleutheroside B; Lilacin;
Molecular formula	C 17 H 24 O 9
Brief description	colorless, needle-shaped crystals
External identifiers / databases
EC number	601-519-0
ECHA InfoCard	100.120.487
PubChem	5316860
ChemSpider	4475831
Wikidata	Q891785
properties
Molar mass	372.37 g mol −1
Physical state	firmly
Melting point	192 ° C
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	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

Close-up of a common lilac

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 ).

[Merck-1] Merck, without further references (PDF; 338 kB).

[Sigma-2] Data sheet Eleutheroside B at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

[3] Alphons Meillet: "Lilacin", in: Justus Liebigs Annalen der Chemie , 1841 , 40 (3), pp. 319-320 ( doi : 10.1002 / jlac.18410400342 ).

[4] 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 ).

[5] Franz J. Bernays: "Ueber das Syringin", in: Pharmaceutisches Central Blatt , 1841 , 12 , pp. 938-939 ( limited preview in Google book search).

[6] 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).

[7] 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 ).