References of 1H,7H-Naphtho[1,8-bc:4,4a-c']difuran-5,10a(8H)-dicarboxylicacid,10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-,5,10a-dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-
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.
![CAS No:11141-17-6 1H,7H-Naphtho[1,8-bc:4,4a-c']difuran-5,10a(8H)-dicarboxylicacid,10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-,5,10a-dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-](/structure/cas-111/11141-17-6.png)
