Title: Aureothin
CAS Registry Number: 2825-00-5
CAS Name: (Z,E)-2-Methoxy-3,5-dimethyl-6-[tetrahydro-4-[2-methyl-3-(4-nitrophenyl)-2-propenylidene]-2-furanyl]-4H-pyran-4-one
Additional Names: mycolutein
Molecular Formula: C22H23NO6
Molecular Weight: 397.42
Percent Composition: C 66.49%, H 5.83%, N 3.52%, O 24.15%
Literature References: Antibiotic by-product of aureothricin, q.v., isolated from the culture of Streptomyces thioluteus. Isoln: K. Maeda, J. Antibiot. 6A, 137 (1953); (as mycolutein): H. Schmitz, R. Woodside, Antibiot. Chemother. 5, 652 (1955). Structure: Y. Hirata et al., Tetrahedron 14, 252 (1961). Identity with mycolutein: J. L. Schwartz et al., J. Antibiot. 29, 236 (1976). Biosynthesis: R. Cardillo et al., Tetrahedron 30, 459 (1974); M. Yamazaki et al., Chem. Pharm. Bull. 23, 569 (1975). Synthesis: Y. Shizuri et al., Chem. Lett. 1987, 1381.
Properties: Yellow prisms, mp 158°. [a]D18 +51° (chloroform). Sol in methanol, ethanol, acetone, chloroform, tetrahydrofuran. Practically insol in water, nonpolar solvents. uv max (ethanol): 257, 346 nm (log e 4.39, 4.27).
Melting point: mp 158°
Optical Rotation: [a]D18 +51° (chloroform)
Absorption maximum: uv max (ethanol): 257, 346 nm (log e 4.39, 4.27) |