4632. Helveticoside

Nomenclature

CAS number: 630-64-8
(3β,5β)-[(2,6-Dideoxy-β-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-19-oxocard-20(22)-enolide; erisimin; erysimin; alleoside A.
C29H42O9; mol wt 534.64.
C 65.15%, H 7.92%, O 26.93%.

Description and references

A β-glycoside consisting of one mole strophanthidin and one mole d-digitoxose. Isoln from Erysimum helveticum (Jacq.) DC. and Erysimum crepidifolium Reichenb., Cruciferae, and structure: Nagata et al., Helv. Chim. Acta 40, 41 (1957); eidem, Festschr. Arthur Stoll 1957, 715; Gmelin, DE 1221764 (1966). From Erysimum spp.: Kowalewski, Helv. Chim. Acta 43, 1314 (1960). Toxicity study: Graebner, Giesel, Arzneim.-Forsch. 22, 1854 (1972).

Derivative

Dihydrate.

Properties

Needles from dil methanol, mp 153-157°. [α]D25 +30.7° (c = 1.5 in methanol); [α]D24 +26.0° (c = 1.1 in chloroform). uv max (ethanol): 217, 304 nm (log ε 4.27, 1.55). Poisonous. LD100 i.v. in cats: 0.104 mg/kg (Graebner, Giesel).

Derivative

3′,4′-Diacetate.
C33H46O11; mol wt 618.71.
C 64.06%, H 7.49%, O 28.45%.

Properties

Prisms from methanol + ether, mp 237-244°. [α]D25 +41.3° (chloroform).