12-04572. Griseoviridin [Archived]

Nomenclature

CAS number: 53216-90-3
GV.
C22H27N3O7S; mol wt 477.53.
C 55.33%, H 5.70%, N 8.80%, O 23.45%, S 6.71%.

Description and 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).

Chemical structure

Properties

Polymorphic crystals, dec 158-166°, or 194-200°, or 230-240° depending on the crystal modification. [α]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.

Derivative

Diacetate.
C26H31N3O9S; mol wt 561.60.
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°, [α]D27 230° (c = 0.44 in methanol). uv max (ethanol): 218 nm (ε 41800).

Status

This monograph has been retired and is no longer subject to revision or update.