5498. Linarin

Nomenclature

CAS number: 480-36-4
7-[[6-O-(6-Deoxy-α-l-mannopyranosyl)-β-d-glucopyranosyl]oxy]-5-hydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one; acacetin-β-rutinoside; linarigenin-glucoside; 5,7-dihydroxy-4′-methoxyflavone-d-glucosido-l-rhamnoside; buddleoflavonoloside.
C28H32O14; mol wt 592.55.
C 56.75%, H 5.44%, O 37.80%.

Description and references

From the flowers of Linaria vulgaris Mill., Scrophulariaceae: Merz, Wu, Arch. Pharm. 274, 126 (1936); from Cirsium oleraceum Scop., Compositae: Wagner et al., ibid. 293, 1053 (1960). Structure: Baker et al., J. Chem. Soc. 1951, 691. Synthesis: Zemplén, Bognàr, Ber. 74, 1818 (1941).

Chemical structure

Derivative

Monohydrate.

Properties

Needles from methanol, mp 268-270°. [α]D26 100° (0.07 g in 10 ml glacial acetic acid); [α]D24 87° (0.05 g in pyridine). Practically insol in water and the usual organic solvents. Sol in nitrobenzene, phenol, aniline, pyridine, concd acids and alkalies. The water of crystn cannot be removed at 100° in vacuo over P2O5 (Merz); may be removed at 138° in high vacuum (Zemplén). Hydrolysis gives 5,7-dihydroxy-4′-methoxyflavone, d-glucose, and l-rhamnose.