2425. Cnicin

Nomenclature

CAS number: 24394-09-0
(3R)-(3aR,4S,6E,10Z,11aR)-3,4-Dihydroxy-2-methylenebutanoic acid 2,3,3a,4,5,8,9,11a-octahydro-10-(hydroxymethyl)-6-methyl-3-methylene-2-oxocyclodeca[b]furan-4-yl ester; (Z,E)-6α,8α,15-trihydroxygermacra-1(10),4,11(13)-trien-12-oic acid 12,6-lactone 8-(3,4-dihydroxy-2-methylenebutyrate); cynisin; centaurin.
C20H26O7; mol wt 378.42.
C 63.48%, H 6.93%, O 29.60%.

Description and references

Bitter principle of Cnicus benedictus L., Compositae. Isolation and review: Korte, Bechmann, Naturwissenschaften 45, 390 (1958). Structure: Suchy et al., Tetrahedron Letters no. 10, 5 (1969); Ber. 93, 2449 (1960). Revised structure: Samek et al., Tetrahedron Lett. 1969, 2931. Stereochemistry: Tori et al., J. Chem. Soc. B 1971, 1084.

Chemical structure

Properties

Crystals, mp 143°. [α]D20 +158° (c = 2.3 in ethanol). uv max: 220 nm (log ε 4.34). Slightly sol in water; freely sol in alcohol. Practically insol in ether.