Viridin
Title: Viridin
CAS Registry Number: 3306-52-3
CAS Name: 1b-Hydroxy-2b-methoxy-18-norandrosta-5,8,11,13-tetraeno[6,5,4-bc]furan-3,7,17-trione
Molecular Formula: C20H16O6
Molecular Weight: 352.34
Percent Composition: C 68.18%, H 4.58%, O 27.25%
Literature References: Antibiotic substance from Gliocladium virens: Grove et al., J. Chem. Soc. 1965, 3803. Previously reported isolation from Trichoderma viride: Brian, McGowan, Nature 156, 144 (1945); Brian et al., Ann. Appl. Biol. 33, 190 (1946). Epimerizes to b-viridin where methoxyl group is equatorial. Separation of the two isomers: Vischer et al., Nature 165, 528 (1950). Structure: Grove et al., Chem. Commun. 1965, 343. Configuration: eidem, J. Chem. Soc. C 1966, 743; Neidle, Hursthouse, J. Chem. Soc. Perkin Trans. 2 1972, 760. Biosynthesis: Blight et al., Chem. Commun. 1968, 1117; Grove, J. Chem. Soc. C 1969, 549.
Properties: Prisms from benzene, mp 245° (dec). [a]D19 -224°. uv max: 242, 300 nm (log e 4.49, 4.22). Needles from acetone, mp 222-224° (dec). Prisms from glacial acetic acid, mp 200-205° (dec). Sol in water, chloroform; sparingly sol in carbon disulfide, carbon tetrachloride. Practically insol in ether, camphor. Aq solns lose activity rapidly unless acidified to pH 3.
Melting point: mp 245° (dec); mp 222-224° (dec); mp 200-205° (dec)
Optical Rotation: [a]D19 -224°
Absorption maximum: uv max: 242, 300 nm (log e 4.49, 4.22)
 
Derivative Type: b-Isomer
Properties: Prisms from benzene, mp 240-245° (dec). [a]D16 -23°. uv max: 243, 300 nm (log e 4.45, 4.25).
Melting point: mp 240-245° (dec)
Optical Rotation: [a]D16 -23°
Absorption maximum: uv max: 243, 300 nm (log e 4.45, 4.25)
 
Therap-Cat: Antifungal.
Keywords: Antifungal (Antibiotics).

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