620. Anabsinthin

Nomenclature

CAS number: 6903-12-4
(3S,3aS,6S,6aR,6bS,7R,7aR,8S,10aS,11S,13aS,13bS,13cR,14bS,15S)-3,3a,4,5,6,6a,6b,7,7a,8,9,10,10a,13a,13c,14b-Hexadecahydro-6-hydroxy-3,6,8,11,14,15-hexamethyl-2H-8,15-epoxy-7,13b-ethanopentaleno[1″,2″:6,7;5″,4″:6′,7′]dicyclohepta[1,2-b:1′,2′-b′]difuran-2,12(11H)-dione; anabsynthin.
C30H40O6; mol wt 496.64.
C 72.55%, H 8.12%, O 19.33%.

Description and references

A bitter principle isolated from Artemisia absinthium L., Compositae (wormwood). Isoln: F. Sorm et al., Chem. Ind. (London) 1955, 569; V. Herout et al., Collect. Czech. Chem. Commun. 21, 1485 (1956). Structure: L. Novotny et al., Chem. Ind. (London) 1958, 465; V. Herout et al., Collect. Czech. Chem. Commun. 25, 1492 (1960); J. Beauhaire et al., Tetrahedron Lett. 21, 3191 (1980).

Chemical structure

Derivative

Anhydrous Form.

Properties

Crystals from benzene or isopropanol + diisopropyl ether, or by drying over phosphorus pentoxide in vacuo, mp 267°. [α]D20 +113° (c = 1.85 in chloroform).

Derivative

Monohydrate.

Properties

Crystals from methanol, mp 210°.