8412. Scutellarein

Nomenclature

CAS number: 529-53-3
5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 4′,5,6,7-tetrahydroxyflavone; 6-hydroxypelargidenon 1465.
C15H10O6; mol wt 286.24.
C 62.94%, H 3.52%, O 33.54%.

Description and references

By hydrolysis of scutellarin: Molisck, Goldschmidt, Monatsh. Chem. 22, 679 (1901); Marsh, Biochem. J. 59, 58 (1955). From Digitalis lanata Ehrh., Scrophulariaceae: Rangaswami, Rao, Proc. Indian Acad. Sci. 54A, 51 (1961), C.A. 56, 10076f (1962). Structure: Wessely, Moser, Monatsh. Chem. 56, 97 (1930). Synthesis: Sastri, Seshadri, Proc. Indian Acad. Sci. 23A, 262 (1946), C.A. 41, 449a (1947); Zemplén et al., Acta Chim. Acad. Sci. Hung. 16, 445 (1958); Jouanne, Mentzer, C. R. Seances Acad. Sci. Ser. C 263, 1022 (1966).

Chemical structure

Properties

Yellow leaflets from methanol, does not melt below 300°. uv max (ethanol): 286, 339 nm (ε 16600; 18300).

Derivative

Tetraacetate.
C23H18O10; mol wt 454.38.
C 60.80%, H 3.99%, O 35.21%.

Properties

Prisms from ethyl acetate, mp 235-237°.

Derivative

Glucuronide.

Nomenclature

Scutellarin.
C21H18O12; mol wt 462.36.
C 54.55%, H 3.92%, O 41.52%.

Description and references

From leaves of Scutellaria altissima Linn., Labiatae: Goldschmiedt, Zerner, Monatsh. Chem. 31, 439 (1910); from Centaurea scabiosa L., Compositae: Charaux, Rabaté, J. Pharm. Chim. 9, 155 (1940); from Scutellaria spp.: Marsh, Biochem. J. 59, 58 (1955); Nature 183, 1824 (1959). Synthesis: Farkas et al., Ber. 107, 3878 (1974).

Properties

Needles from alc, darkens above 230°, does not melt below 300°. [α]D18 -14° (water); [α]D20 -139° (pyridine). uv max (ethanol): 285, 335 nm (ε 20000; 26100). Practically insol in water. Sol in alkali hydroxides, glacial acetic acid; slightly sol in organic solvents.