4925. Imperatorin

Nomenclature

CAS number: 482-44-0
9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one; 6-hydroxy-7-(3-methyl-2-butenyloxy)-5-benzofuranacrylic acid δ-lactone; 8-isoamylenoxypsoralen; marmelosin; ammidin; pentosalen.
C16H14O4; mol wt 270.28.
C 71.10%, H 5.22%, O 23.68%.

Description and references

From roots of Imperatoria osthruthium L., Umbelliferae: Spth, Holzen, Ber. 66, 1137 (1933); from seeds of Angelica archangelica L.: Spth, Vierhapper, ibid. 71, 1667 (1938); from fruit of Pastinaca sativa L., Umbelliferae: Soine et al., J. Am. Pharm. Assoc. 45, 426 (1956). Identity with marmelosin: Spth et al., Ber. 70, 1021 (1937). Identity with ammidin: Fahmy, Abu-Shady, Q. J. Pharm. Pharmacol. 21, 499 (1948). Partial synthesis: Spth, Holzen, Ber. 68, 1123 (1935). Synthesis: Spth, Vierhapper, ibid. 70, 248 (1937).

Chemical structure

Properties

Prisms from ether, long fine needles from hot water, mp 102°. Practically insol in cold water. Very sparingly sol in boiling water; freely sol in chloroform; sol in benzene, alcohol, ether, petr ether, alkali hydroxides. uv max: 302, 265, 250 nm (log ε 3.95, 4.00, 4.24).