2250. Chrysanthemaxanthin

Nomenclature

CAS number: 27780-11-6
(3S,3′R,5R,6′R,8S)-5,8-Epoxy-5,8-dihydro-β,ε-carotene-3,3′-diol.
C40H56O3; mol wt 584.87.
C 82.14%, H 9.65%, O 8.21%.

Description and references

Carotenoid pigment. Occurs together with flavoxanthin, q.v.. Has same structural formula, mp, rotation, and absorption as flavoxanthin, but differs sterically. Can be separated chromatographically: in a zinc carbonate column the chrysanthemaxanthin zone locates itself below flavoxanthin and above lutein epoxide. Isoln from asters: Karrer, Jucker, Helv. Chim. Acta 26, 626 (1943). Partial synthesis from lutein, eidem, ibid. 28, 300 (1945). For absolute configuration see: H. Cadosch et al., ibid. 61, 783 (1978).

Chemical structure

Properties

Golden yellow leaflets, mp 184-185°, also reported as mp 178.5-180° (Codosch). [α]D23 +104° ±5% (c = 1.833 mg/ml in chloroform). Absorption max (CHCl3): 459, 430 nm. uv max (ethanol): 204, 251, 298, 311, 399, 422, 448 nm (ε 27300, 28800, 10000, 13100, 97700, 150400, 148500). Freely sol in chloroform, benzene, acetone. Less sol in methanol, ethanol. Almost insol in petr ether.

Note

Chrysanthemaxanthin has no vitamin A activity.