4285. Fulvoplumierin

Nomenclature

CAS number: 20867-01-0
(7E)-7-(2E)-Butenylidene-1,7-dihydro-1-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester; 3-(2-butenylidene)-2-carboxy-α-(hydroxymethylene)-1,4-cyclopentadiene-1-acetic acid δ-lactone methyl ester; methyl 7-crotonylidenecyclopenta[c]pyran-1-(7H)-one-4-carboxylate.
C14H12O4; mol wt 244.24.
C 68.85%, H 4.95%, O 26.20%.

Description and references

Occurs together with plumieride and plumericin. Isoln from Plumeria acutifolia Poir., Apocynaceae, also from roots of P. rubra var alba: Grumbach et al., Experientia 8, 224 (1952). Structure: Schmid, Bencze, Helv. Chim. Acta 36, 206, 1468 (1953). Stereochemistry: Albers-Schnberg et al., ibid. 45, 1406 (1962). Synthesis: Büchi, Carlson, J. Am. Chem. Soc. 90, 5336 (1968); 91, 6470 (1969).

Chemical structure

Properties

Orange needles from chloroform + petr ether, ethyl acetate, or alcohol, dec 151-152°. Sublimes in high vacuum. uv max (ethanol): 272, 365 nm (ε 7,000; 33,700). Sol in chloroform, hot ethyl acetate, benzene, alcohol; less sol in pyridine, acetone. Practically insol in water, petr ether.