3543. Elenolide

Nomenclature

CAS number: 24582-91-0
(4S)-4-[(1E)-1-Formyl-1-propenyl]-3,4-dihydro-2-oxo-2H-pyran-5-carboxylic acid methyl ester.
C11H12O5; mol wt 224.21.
C 58.93%, H 5.39%, O 35.68%.

Description and references

Hypotensive lactone from fruits, bark and leaves of the olive tree, Olea europaea L., Oleaceae: Veer et al., Rec. Trav. Chim. 76, 839 (1957); GB 789427 (1958 to Organon); US 3033877 (1962 to Organon). Structure: Panizzi et al., Gazz. Chim. Ital. 90, 1464 (1960); Beyerman et al., Bull. Soc. Chim. Fr. 1961, 1812. Synthesis from secologanin: L. F. Tietze, H. C. Uzar, Angew. Chem. Int. Ed. 18, 539 (1979).

Chemical structure

Properties

Needles from hot alc, mp 155.5°. [α]D20 +369° (chloroform). uv max (ethanol): 225, 317 nm (log ε 4.29, 1.75).