Griseoviridin

Title: Griseoviridin
CAS Registry Number: 53216-90-3
Additional Names: GV
Molecular Formula: C22H27N3O7S
Molecular Weight: 477.53
Percent Composition: C 55.33%, H 5.70%, N 8.80%, O 23.45%, S 6.71%
Literature References: Antibiotic substance obtained together with Etamycin (viridogrisein) from Streptomyces griseus: Bartz et al., Antibiot. Annu. 1954-1955, 777. Characterization: Ames et al., J. Chem. Soc. 1955, 4260; Ames, Bowman, ibid. 1955, 4264. Structure studies: Fallona et al., J. Am. Chem. Soc. 84, 4162 (1962); eidem, Can. J. Chem. 42, 371, 394 (1964). Revised structure: G. I. Birnbaum, S. R. Hall, J. Am. Chem. Soc. 98, 1926 (1976). Absolute configuration: B. W. Bycroft, T. J. King, J. Chem. Soc. Perkin Trans. 1 1976, 1996. Production of griseoviridin and viridogrisein: Bartz et al., US 3023204 (1962 to Parke, Davis). Synthetic study: A. I. Meyers, R. A. Amos, J. Am. Chem. Soc. 102, 870 (1980).
Properties: Polymorphic crystals, dec 158-166°, or 194-200°, or 230-240° depending on the crystal modification. [a]D27 -237° (c = 0.5 in methanol). uv max (methanol): 221 nm (E1%1cm 870). Sol in pyridine, moderately sol in lower alcohols, sparingly sol in water and nonpolar solvents.
Optical Rotation: [a]D27 -237° (c = 0.5 in methanol)
Absorption maximum: uv max (methanol): 221 nm (E1%1cm 870)
Derivative Type: Diacetate
Molecular Formula: C26H31N3O9S
Molecular Weight: 561.60
Percent Composition: C 55.61%, H 5.56%, N 7.48%, O 25.64%, S 5.71%
Properties: Needles from methanol + ether + petr ether, dec 137-140°, [a]D27 -230° (c = 0.44 in methanol). uv max (ethanol): 218 nm (e 41800).
Optical Rotation: [a]D27 -230° (c = 0.44 in methanol)
Absorption maximum: uv max (ethanol): 218 nm (e 41800)
Status: This monograph has been retired and is no longer subject to revision or update.
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