Rotenone

• Catalog No.: Bio-0310
• CAS Number: 83-79-4
• M. F.: C23H22O6
• M. W.: 394.41718

SYNONYMS

• IUPAC name: (1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^3,^1^1.0^4,^8.0^1^4,^1^9]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
• IUPAC Traditional name: (1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^3,^1^1.0^4,^8.0^1^4,^1^9]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
• Synonyms: Noxfish; Derrin; Paraderil; Dactinol; Derris; Dri-kil; Nicouline; Tubotoxin

DATABASE IDS

• CAS Number: 83-79-4

PROPERTIES

• Application(s): Antineoplastic agent
• Application(s): Contact insecticide and pesticide
• Application(s): Potent mitochondrial poison
• Biological Source: Constit. of the root of Derris elliptica . Widely distrib. in the Leguminosae (Papilionoideae) e.g. in many other Derris spp. Lonchocarpus spp. Millettia spp., Tephrosia spp., Amorpha fruticosa, Antheroporum pierrei, Crotalaria burhia, Crotalaria medicaginea, Mundulea pauciflora, Mundulea sericea, Neorautanenia amboensis, Neorautanenia ficifolia, Ormocarpum glabrum, Pachyrrhizus erosus, Piscidia erythrina, Piscidia mollis, Poiretia tetraphylla and Spatholobus roxburghii. Also in Verbascum thapsus (Scrophulariaceae)
• Mechanism of Action: Inhibits the transfer of electrons from Fe-S centers in Complex I to ubiquinone

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 99A, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 923A, (nmr)
• Bchi, G. et al., J.C.S., 1961, 2843, (abs config)
• Reed, R.I. et al., J.C.S., 1963, 5949, (ms)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 1424, (occur)
• Unai, T. et al., Agric. Biol. Chem., 1973, 37, 387; 897, (synth)
• Crombie, L. et al., J.C.S. Perkin 1, 1973, 1277; 1285; 1975, 1497, (synth, biosynth, cmr)
• Carlson, D.G. et al., Tetrahedron, 1973, 29, 2731, (pmr)
• Begley, M.J. et al., Chem. Comm., 1975, 850, (cryst struct)
• Haley, T.J., J. Environ. Pathol. Toxicol., 1978, 1, 315, (rev)
• Sasaki, I. et al., Agric. Biol. Chem., 1979, 43, 137, (synth)
• Ingham, J.L., Prog. Chem. Org. Nat. Prod., 1983, 43, 1, (rev, occur)
• Abidi, S.L., J. Het. Chem., 1987, 24, 845, (hplc, resoln)
• Rossi, M. et al., Bioorg. Chem., 1988, 16, 376, (cryst struct, conformn)
• Nunlist, R. et al., J. Het. Chem., 1988, 25, 351, (pmr, cmr)
• Dangerous Prop. Ind. Mater. Rep., 1989, 9, 74, (rev, tox)
• Blasko, G. et al., J. Nat. Prod., 1989, 52, 1363, (cmr)
• Pesticide Manual, 9th edn., 1991, No. 10610
• Agrochemicals Handbook, 3rd edn., Royal Society of Chemistry, 1992, A363
• Bhandari, P. et al., J.C.S. Perkin 1, 1992, 839; 851, (biosynth)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1131
• Hayashi, H. et al., Biosci., Biotechnol., Biochem., 1997, 61, 914-916, (activity)
• Crombie, L. et al., Phytochemistry, 1998, 49, 1479-1507, (rev, biosynth)
• Handbook of Pesticide Toxicology, (Eds. Hayes, W.J. et al), Academic Press, 1991, 599, (tox, rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, RNZ000