6878. Oroxylin A

Nomenclature

CAS number: 480-11-5
5,7-Dihydroxy-6-methoxy-2-phenyl-4H-1-benzopyran-4-one; 5,7-dihydroxy-6-methoxyflavone; oroxylin.
C16H12O5; mol wt 284.26.
C 67.60%, H 4.26%, O 28.14%.

Description and references

From root bark of Oroxylum indicum Vent., Bignoniaceae: Naylor, Chaplin, Pharm. J. 20, 257 (1890); Naylor, Dyer, J. Chem. Soc. 79, 954 (1901); Row et al., Proc. Indian Acad. Sci. 28A, 189 (1948). Structure: Shah et al., J. Chem. Soc. 1936, 591; 1938, 1555. Synthesis: Murti, Seshadri, Proc. Indian Acad. Sci. 29A, 1 (1949); Sarin, Seshadri, J. Sci. Ind. Res. 19B, 117 (1960); Molho, Gerphagnon, Bull. Soc. Chim. Fr. 1963, 607; Varady, Tetrahedron Lett. 1965, 4281.

Chemical structure

Properties

Yellow plates from ethanol, mp 231-232°. Sol in alc, acetone, hot benzene, ether, alkalies, glacial acetic acid; sparingly sol in chloroform; practically insol in water.

Derivative

Diacetyl oroxylin.
C20H16O7; mol wt 368.34.
C 65.22%, H 4.38%, O 30.41%.

Properties

Needles from alcohol, mp 131-132°.