4399. Gentisin

Nomenclature

CAS number: 437-50-3
1,7-Dihydroxy-3-methoxy-9H-xanthen-9-one; 4,7-dihydroxy-2-methoxyxanthone; gentianic acid; gentianin; gentiin.
C14H10O5; mol wt 258.23.
C 65.12%, H 3.90%, O 30.98%.

Description and references

From root of Gentiana lutea L., Gentianaceae: Henry, Caventou, J. Pharm. Chim. 1821, 178; Canonica, Pelizzoni, Gazz. Chim. Ital. 85, 1007 (1955). Structure: Korte, Ber. 87, 1357 (1954). Synthesis: Anand, Venkataraman, Proc. Indian Acad. Sci. 25A, 438 (1947); Rao, Seshadri, ibid. 37A, 710 (1953).

Chemical structure

Properties

Yellow needles from alc, mp 266-267°. Absorption max (methanol): 260, 275, 315, 410 nm (log ε 4.35, 4.30, 4.10, 3.70). Very slightly sol in water or organic solvents.

Derivative

Diacetate.
C18H14O7; mol wt 342.30.
C 63.16%, H 4.12%, O 32.72%.

Properties

Crystals from alc, mp 196-197°. uv max (methanol): 240, 270, 300 nm (log ε 4.58, 4.05, 4.10).