12-09220. Tanghinigenin [Archived]

Nomenclature

CAS number: 6875-16-7
(3β,5β,7β)-7,8-Epoxy-3,14-dihydroxycard-20(22)-enolide.
C23H32O5; mol wt 388.50.
C 71.11%, H 8.30%, O 20.59%.

Description and references

Isoln from glucosides: Sigg et al., Helv. Chim. Acta 38, 166 (1955). Structure: Flury, Reichstein, Ann. Chim. (Rome) 53, 23 (1963); Flury et al., Helv. Chim. Acta 48, 1113 (1965). Toxicity study: Chen, Henderson, J. Pharmacol. Exp. Ther. 111, 365 (1954).

Chemical structure

Properties

Prisms from acetone + petr ether, mp 187-188°. [α]D25 +14.1° (c = 1.138 in chloroform). uv max: 217 nm (log ε 4.22). LD50 i.v. in cats: 1 mg/kg (Chen, Henderson).

Derivative

Acetate.

Nomenclature

Acetyltanghinigenin.
C25H34O6; mol wt 430.53.
C 69.74%, H 7.96%, O 22.30%.

Properties

Prisms from acetone + petr ether, mp 241-243°. [α]D24 +14.9° (c = 1.075 in chloroform).

Derivative

3-[(2-O-Acetyl-6-deoxy-3-O-methyl-α-l-glucopyranosyl)oxy].

Nomenclature

CAS number: 25390-16-3
Tanghinin.
C32H46O10; mol wt 590.70.
C 65.07%, H 7.85%, O 27.09%.

Description and references

From the seed of Tanghinia madagascariensis Pet., Apocynaceae and Tanghinia venenifera Poir., Apocynaceae. Isoln: Arnaud, Compt. Rend. 108, 1255 (1889); Frèrejacque et al., ibid. 226, 268 (1948).

Properties

Leaflets from methanol + ether, mp 128-131°. [α]D21 81.5° (c = 1.092 in methanol). LD50 i.v. in cats: 0.4 mg/kg (Chen, Henderson).

Status

This monograph has been retired and is no longer subject to revision or update.