385. Ambrosin

Nomenclature

CAS number: 509-93-3
3,3a,4,5,6,6a,9a,9b-Octahydro-6,9a-dimethyl-3-methyleneazuleno[4,5-b]furan-2,9-dione; 6β-hydroxy-4-oxo-10αH-ambrosa-2,11(13)-dien-12-oic acid γ-lactone.
C15H18O3; mol wt 246.30.
C 73.15%, H 7.37%, O 19.49%.

Description and references

From herb of Ambrosia maritima L., Compositae: Abu-Shady, Soine, J. Am. Pharm. Assoc. 42, 387 (1953); 43, 365 (1954). Structure: Bernardi, Büchi, Experientia 13, 466 (1957); Sorm et al., Collect. Czech. Chem. Commun. 24, 1548 (1959); Nerz et al., J. Am. Chem. Soc. 84, 2601 (1962). Absolute configuration: Emerson et al., Tetrahedron Lett. 1966, 6151. Stereospecific total synthesis of (±)-form: P. A. Grieco et al., J. Am. Chem. Soc. 99, 7393 (1977).

Chemical structure

Properties

Crystals from alc, mp 146°. [α]D22 154.50° (c = 2 in alcohol). uv max (95% ethanol): 217, 324 nm (ε 13465; 36). Very sol in chloroform; sol in alc, benzene, sparingly sol in ether, petr ether. Practically insol in water, cold dil NaOH, dil acids.

Derivative

(±)-Form.

Properties

mp 188-190°.