4088. Fisetin

Nomenclature

CAS number: 528-48-3
2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-one; 3,3′,4′,7-tetrahydroxyflavone; 5-desoxyquercetin; fisidenolon 1521; C.I. 75620; C.I. Natural Brown 1.
C15H10O6; mol wt 286.24.
C 62.94%, H 3.52%, O 33.54%.

Description and references

Flavanoid present in the bark and stems of a variety of trees. Isolation from Rhus cotinus L. Anacardiaceae, Venetian Sumach: Chevreul, Lecons Chim. Appl. a la Teint. 2, 169 (1833) [cf. J. Schmid, Ber. 19, 1734 (1886)]; from heartwood of Acacia spp, Leguminosae: Roux et al., Biochem. J. 78, 834 (1961). Structure: Seshadri, Annu. Rev. Biochem. 20, 492 (1951). Synthesis: St. Kostanecki et al., Ber. 37, 784 (1904); J. Allan, R. Robinson, J. Chem. Soc. 129, 2334 (1926). Inhibition of aflatoxin cytotoxicity: A. G. Schwartz, W. R. Rate, J. Environ. Pathol. Toxicol. 2, 1021 (1979). Mutagenicity studies: J. P. Brown et al., Biochem. Soc. Trans. 5, 1489 (1977); idem, P. S. Dietrich, Mutat. Res. 66, 223 (1979). TLC determn: D. Heimler, J. Chromatogr. 366, 407 (1986).

Chemical structure

Properties

Yellow needles from dil alc, dec 330°. uv max (ethanol): 252, 320, 360 nm (log E1%1cm 2.62, 2.51, 2.73). Sol in alcohol, acetone, acetic acid, solns of fixed alkali hydroxides. Practically insol in water, ether, benzene, chloroform and petr ether.