Tanghinigenin
Title: Tanghinigenin
CAS Registry Number: 6875-16-7
CAS Name: (3b,5b,7b)-7,8-Epoxy-3,14-dihydroxycard-20(22)-enolide
Molecular Formula: C23H32O5
Molecular Weight: 388.50
Percent Composition: C 71.11%, H 8.30%, O 20.59%
Literature 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).
Properties: Prisms from acetone + petr ether, mp 187-188°. [a]D25 +14.1° (c = 1.138 in chloroform). uv max: 217 nm (log e 4.22). LD50 i.v. in cats: 1 mg/kg (Chen, Henderson).
Melting point: mp 187-188°
Optical Rotation: [a]D25 +14.1° (c = 1.138 in chloroform)
Absorption maximum: uv max: 217 nm (log e 4.22)
Toxicity data: LD50 i.v. in cats: 1 mg/kg (Chen, Henderson)
 
Derivative Type: Acetate
Additional Names: Acetyltanghinigenin
Molecular Formula: C25H34O6
Molecular Weight: 430.53
Percent Composition: C 69.74%, H 7.96%, O 22.30%
Properties: Prisms from acetone + petr ether, mp 241-243°. [a]D24 +14.9° (c = 1.075 in chloroform).
Melting point: mp 241-243°
Optical Rotation: [a]D24 +14.9° (c = 1.075 in chloroform)
 
Derivative Type: 3-[(2-O-Acetyl-6-deoxy-3-O-methyl-a-L-glucopyranosyl)oxy]
CAS Registry Number: 25390-16-3
Additional Names: Tanghinin
Molecular Formula: C32H46O10
Molecular Weight: 590.70
Percent Composition: C 65.07%, H 7.85%, O 27.09%
Literature 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°. [a]D21 -81.5° (c = 1.092 in methanol). LD50 i.v. in cats: 0.4 mg/kg (Chen, Henderson).
Melting point: mp 128-131°
Optical Rotation: [a]D21 -81.5° (c = 1.092 in methanol)
Toxicity data: 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.

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