Title: Scutellarein
CAS Registry Number: 529-53-3
CAS Name: 5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Additional Names: 4¢,5,6,7-tetrahydroxyflavone; 6-hydroxypelargidenon 1465
Molecular Formula: C15H10O6
Molecular Weight: 286.24
Percent Composition: C 62.94%, H 3.52%, O 33.54%
Literature 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).
Properties: Yellow leaflets from methanol, does not melt below 300°. uv max (ethanol): 286, 339 nm (e 16600; 18300).
Absorption maximum: uv max (ethanol): 286, 339 nm (e 16600; 18300)
Derivative Type: Tetraacetate
Molecular Formula: C23H18O10
Molecular Weight: 454.38
Percent Composition: C 60.80%, H 3.99%, O 35.21%
Properties: Prisms from ethyl acetate, mp 235-237°.
Melting point: mp 235-237°
Derivative Type: Glucuronide
Additional Names: Scutellarin
Molecular Formula: C21H18O12
Molecular Weight: 462.36
Percent Composition: C 54.55%, H 3.92%, O 41.52%
Literature 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°. [a]D18 -14° (water); [a]D20 -139° (pyridine). uv max (ethanol): 285, 335 nm (e 20000; 26100). Practically insol in water. Sol in alkali hydroxides, glacial acetic acid; slightly sol in organic solvents.
Optical Rotation: [a]D18 -14° (water); [a]D20 -139° (pyridine)
Absorption maximum: uv max (ethanol): 285, 335 nm (e 20000; 26100)
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