Aureothin

• Catalog No.: Bio-0210
• CAS Number: 2825-00-5
• M. F.: C22H23NO6
• M. W.: 397.42112

SYNONYMS

• IUPAC name: 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]oxolan-2-yl]-4H-pyran-4-one
• IUPAC Traditional name: 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]oxolan-2-yl]-4H-pyran-4-one
• Synonyms: Distacyne; Antibiotic 74A''; Distacin; Mycolutein; Antibiotic 2814K; Antibiotic JA 2814K

DATABASE IDS

• CAS Number: 2825-00-5

PROPERTIES

• Application(s): Antitumour
• Application(s): Antifungal
• Application(s): Antibacterial
• Application(s): Possesses insecticidal and pesticidal props.
• Biological Source: Isol. from Streptomyces thioluteus, Streptomyces distallicus, Streptomyces luteoreticuli, Streptomyces netropsis and Streptoverticillium mycoheptinicum. Also from Actinomyces netropsis strain 2129
• Description: (R)-form
• Mechanism of Action: Non-competitive NADH-ubiquinone oxidoreductase (NADH dehydrogenase) inhibitor

REFERENCES

• Hirata, Y. et al., Tetrahedron, 1961, 14, 252, (isol, struct, uv)
• Oishi, H. et al., Agric. Biol. Chem., 1969, 33, 1990
• Cardillo, R. et al., Tetrahedron, 1974, 30, 459, (biosynth)
• Yamazaki, M. et al., Chem. Pharm. Bull., 1975, 23, 569, (isol, cmr, biosynth)
• Athunov, A.A. et al., Khim. Prir. Soedin., 1975, 11, 114; Chem. Nat. Compd. (Engl. Transl.), 1975, 11, 136, (isol, uv, pmr)
• Schwartz, J.L. et al., J. Antibiot., 1976, 29, 236
• Severinets, L.Y. et al., Antibiotiki (Moscow), 1978, 23, 7, (isol)
• Shizuri, Y. et al., Chem. Lett., 1987, 1381, (synth)
• Ishibashi, Y. et al., Tet. Lett., 1992, 33, 521, (abs config)
• Ishibashi, Y. et al., Bull. Chem. Soc. Jpn., 1995, 68, 3643, (abs config, cryst struct)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DTU200