9016. Syringin

Nomenclature

CAS number: 118-34-3
(E)-4-(3-Hydroxy-1-propenyl)-2,6-dimethoxyphenyl-β-d-glucopyranoside; 4-(3-hydroxypropenyl)-2,6-dimethoxyphenyl-d-glucoside; syringoside; ligustrin; lilacin; methoxyconiferine.
C17H24O9; mol wt 372.37.
C 54.83%, H 6.50%, O 38.67%.

Description and references

First isolated by Meillet in 1841 from bark of Syringa vulgaris L. (lilac): Ann. 40, 319 (1841). Prepn: Pauly, Strassberger, Ber. 62, 2277 (1929); Freudenberg, Schraube, Ber. 88, 16 (1955). Isoln from lilac bark: Freudenberg et al., Ber. 84, 472 (1951); from various plants: Plouvier, Compt. Rend. 254,4196 (1962); from cambial sap of spruce: Freudenberg, Harkin, Phytochemistry 2, 189 (1963).

Chemical structure

Derivative

Monohydrate.

Properties

Crystals from water, mp 192°. [α]D20 8.2° (c = 2.43 in chloroform), 17.25° (water). Slightly sol in cold water; sol in hot water, alc. Practically insol in ether.