8972. Sulfuretin

Nomenclature

CAS number: 120-05-8
(Z)-2-[(3,4-Dihydroxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone; 2-(3,4-dihydroxybenzylidene)-6-hydroxy-3(2H)-benzofuranone; 3′,4′,6-trihydroxyaurone; 3′,4′,6-trihydroxybenzalcoumaranone.
C15H10O5; mol wt 270.24.
C 66.67%, H 3.73%, O 29.60%.

Description and references

Flavonoid pigment responsible for the yellow color of certain species of Compositae. Isoln from Cosmos sulphureus Cav., Compositae: Shimokoriyama, Hattori, J. Am. Chem. Soc. 75, 1900 (1953); from Dahlia variabilis Desf., Compositae: Nordstrm, Swain, Arch. Biochem. Biophys. 60, 329 (1956). Prepn by condensation of 6-hydroxy-3-coumaranone and protocatechuic alcohol: Nordstrm, Swain, ibid. Prepn and structure studies: Geissman, Jurd, J. Am. Chem. Soc. 76, 4475 (1954); Farkas et al., Ber. 92, 2847 (1959). Structure: Shimokoriyama, Geissman, J. Org. Chem. 25, 1956 (1960).

Chemical structure

Properties

Orange crystals from dil alc, mp 280-285° (Shimokoriyama), mp 315° (dec) (Nordstrm), mp 302-304° (Farkas). uv max: 398 nm.

Derivative

Triacetate.
C21H16O8; mol wt 396.35.
C 63.64%, H 4.07%, O 32.29%.

Properties

Pale yellow needles from methanol, mp 191-194° (Shimokoriyama), mp 167-168° (Nordstrm).