Title: Peucedanin
CAS Registry Number: 133-26-6
CAS Name: 3-Methoxy-2-(1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
Additional Names: 6-hydroxy-2-isopropyl-3-methoxy-5-benzofuranacrylic acid d-lactone; 4-methoxy-5-isopropylfuro[2,3:6,7]coumarin; oreoselone methyl ether
Molecular Formula: C15H14O4
Molecular Weight: 258.27
Percent Composition: C 69.76%, H 5.46%, O 24.78%
Literature References: Coumarin deriv obtained from rhizome of Peucedanum officinale L., Umbelliferae: Schlatter, Ann. 5, 201 (1833); Hlasiwetz, Weidel, ibid. 174, 67 (1874); A. Jassoy, P. Haensel, Arch. Pharm. 236, 662 (1898); Popper, Monatsh. Chem. 19, 268 (1898); from Peucedanum morisonii, Bess., Umbelliferae: G. K. Nikonov, A. A. Ivashenko, Zh. Obshch. Khim. 33, 2740 (1963). Fluorescence spectrum: R. H. Goodwin, F. Kavanagh, Arch. Biochem. 27, 182 (1950). Antitumor activity and toxicity studies: E. M. Vermel, S. A. Kruglyak-Syrkina, Vopr. Onkol. 5, 43 (1959), C.A. 53, 19162h (1959). Structure: E. Späth et al., Ber. 64, 2203 (1931); E. Späth, K. Klager, ibid. 66, 749 (1933). Synthesis: H. Schmid, A. Ebnöther, Helv. Chim. Acta 34, 1982 (1951).
Properties: Colorless needles from ether/petr ether, mp 84-87°; also reported as mp 95-97° (Schmid, Ebnöther); from ligroin, mp 102.5° (Nikonov, Ivashenko). uv max (methanol): 255, 295, 340 nm (log e 4.40, 4.05, 3.70). Practically insol in water. Freely sol in chloroform, CS2; sol in hot alcohol, ether, acetic acid; sparingly sol in benzene, petr ether. LD50 orally in mice: 315 mg/kg (Vermel, Kruglyak-Syrkina).
Melting point: mp 84-87°; mp 95-97° (Schmid, Ebnöther); mp 102.5° (Nikonov, Ivashenko)
Absorption maximum: uv max (methanol): 255, 295, 340 nm (log e 4.40, 4.05, 3.70)
Toxicity data: LD50 orally in mice: 315 mg/kg (Vermel, Kruglyak-Syrkina) |