Structural Formula Vector Image
Title: Azadirachtin
CAS Registry Number: 11141-17-6
Molecular Formula: C35H44O16
Molecular Weight: 720.71
Percent Composition: C 58.33%, H 6.15%, O 35.52%
Literature References: A tetranortriterpinoid isolated from the seeds of the neem tree, Azadirachta indica A. Juss. (Melia azadirachta L.), Meliaceae, and the chinaberry tree, M. azedarach L. Highly active insect feeding deterrent and growth regulator. Isoln from A. indica and identification as feeding inhibitor in locusts: J. H. Butterworth, E. D. Morgan, Chem. Commun. 1968, 23; from M. azedarach: E. D. Morgan, M. D. Thornton, Phytochemistry 12, 391 (1973). Partial synthesis: D. Pflieger et al., Tetrahedron Lett. 28, 1519 (1987). Structural studies: J. H. Butterworth et al., J. Chem. Soc. Perkin Trans. 2 1972, 2445. 1H- and 13C-NMR data and structure: P. R. Zanno et al., J. Am. Chem. Soc. 97, 1975 (1975); K. Nakanishi in Recent Advances in Phytochemistry vol. 9, V. C. Runeckles, Ed. (Plenum Press, New York, 1975) pp 283-298. Revised structure: W. Kraus et al., Tetrahedron Lett. 26, 6435 (1985); H. B. Broughton et al., Chem. Commun. 1986, 46. Isoln by HPLC: E. C. Uebel et al., J. Liq. Chromatogr. 2, 875 (1979); J. D. Warthen, Jr. et al., ibid. 7, 591 (1984). Antifeedant activity in locusts: J. S. Gill, C. T. Lewis, Nature 232, 402 (1971); in fall army worms, cotton bollworms: J. A. Klocke, I. Kubo, Entomol. Exp. Appl. 32, 299 (1982). Insect ecdysis and growth inhibition: H. Rembold, K. P. Sieber, Z. Naturforsch. 36C, 466 (1981); I. Kubo, J. A. Klocke, Agric. Biol. Chem. 46, 1951 (1982); K. P. Sieber, H. Rembold, J. Insect Physiol. 29, 523 (1983). Series of articles on chemistry and activity: Natural Pesticides from the Neem Tree, Proc. 1st Int. Neem Conf., 1980, H. Schmutterer et al., Eds. (German Agency for Technical Cooperation, Eschborn, 1981) 291 pp.
Properties: Microcrystalline powder from carbon tetrachloride, mp 154-158°. [a]D -53° (c = 0.5 in CHCl3). uv max (methanol): 217 nm (e 9100).
Melting point: mp 154-158°
Optical Rotation: [a]D -53° (c = 0.5 in CHCl3)
Absorption maximum: uv max (methanol): 217 nm (e 9100)
Use: Experimentally as insect control agent.

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