4394. Gentianine

Nomenclature

CAS number: 439-89-4
5-Ethenyl-3,4-dihydro-1H-pyrano[3,4-c]pyridin-1-one; 4-(2-hydroxyethyl)-5-vinylnicotinic acid δ-lactone; erythricine.
C10H9NO2; mol wt 175.18.
C 68.56%, H 5.18%, N 8.00%, O 18.27%.

Description and references

From Gentiana kirilowi, Gentianaceae: Proskurnina, J. Gen. Chem. USSR 14, 1148 (1944), C.A. 40, 7213 (1946); from Anthocleista procera Afz. and Fagraea fragrans Roxb., Loganiaceae: Lavie, Taylor-Smith, Chem. Ind. (London) 1963, 781; Wan, Chow, J. Pharm. Pharmacol. 16, 484 (1964). Isoln from Slevogtia orientalis Gris., Gentianaceae, structure and synthesis: Govindachari et al., J. Chem. Soc. 1957, 551, 2725.

Chemical structure

Properties

Needles from ether or petr ether, mp 82-83°. uv max: 220 nm (log ε 4.38). Sol in alkali.

Derivative

Hydrochloride.
C10H9NO2.HCl; mol wt 211.64.
C 56.75%, H 4.76%, N 6.62%, O 15.12%, Cl 16.75%.

Properties

Needles from alcohol + ether, dec 169-170°.

Derivative

Dihydrogentianine.
C10H11NO2; mol wt 177.20.
C 67.78%, H 6.26%, N 7.90%, O 18.06%.

Properties

Crystals from ether + petr ether, mp 74-76°. uv max: 270 nm (log ε 3.4).