Title: Ergoflavin
CAS Registry Number: 3101-51-7
CAS Name: (1S,1¢S,3S,3¢S,4S,4¢S,4aS,4¢aS,9aR,9¢aR)-1,1¢,3,3¢,4,4¢,9a,9¢a-Octahydro-4,4¢,8,8¢,9a,9¢a-hexahydroxy-3,3¢-dimethyl-[7,7¢-bi-1,4a-(epoxymethano)-4aH-xanthene]-9,9¢,11,11¢(2H,2¢H)-tetrone
Additional Names: ergochrome CC(2,2¢)
Molecular Formula: C30H26O14
Molecular Weight: 610.52
Percent Composition: C 59.02%, H 4.29%, O 36.69%
Literature References: Principal pigment from ergot: Freeborn, Pharm. J. 88, 568 (1912); Eglinton et al., J. Chem. Soc. 1958, 1833. Structure: McPhail et al., ibid. 1966, Sect. B, 18. Review of ergoflavin and other ergochromes: Franck, Flasch in Fortschr. Chem. Org. Naturst. 30, 151-206 (1973).
Properties: Yellow needles from methanol, decomp 350°. [a]D21 +37.5° (c = 1.236 in acetone). uv max: 240, 260, 381 nm (E1%1cm 350, 346, 130). Sol in acetone, pyridine; moderately sol in methanol, alcohol, ethyl acetate, dioxane; sparingly sol in ether, benzene. Practically insol in 2N aq NaHCO3.
Optical Rotation: [a]D21 +37.5° (c = 1.236 in acetone)
Absorption maximum: uv max: 240, 260, 381 nm (E1%1cm 350, 346, 130)
Derivative Type: Hexaacetate
Molecular Formula: C42H38O20
Molecular Weight: 862.74
Percent Composition: C 58.47%, H 4.44%, O 37.09%
Properties: Prisms from chloroform + petr ether, dec 248-249°. [a]D20 +61.2° (c = 0.62 in dioxane). uv max: 340, 338 nm (E1%1cm 343, 61).
Optical Rotation: [a]D20 +61.2° (c = 0.62 in dioxane)
Absorption maximum: uv max: 340, 338 nm (E1%1cm 343, 61)
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