Azadirachtin

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ImageFile = Azadirachtin.png ImageSize = 200px
IUPACName = dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-acetoxy-3,5-dihydroxy-4- [(1aR,2S,3aS,6aS,7S,7aS)-6a-hydroxy-7a-methyl-3a,6a,7,7a-tetrahydro-2,7-methanofuro [2,3-b] oxireno [e] oxepin-1a(2H)-yl] -4-methyl-8-{ [(2E)-2-methylbut-2-enoyl] oxy}octahydro-1H-naphtho [1,8a-c:4,5-b'c'] difuran-5,10a(8H)-dicarboxylate

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Section1 = Chembox Identifiers
CASNo = 11141-17-6
PubChem = 5281303
SMILES = CC=C(/C)C(=O)O [C@H] 1C [C@H] ( [C@] 2(CO [C@@H] 3 [C@@H] 2 [C@] 14CO [C@@] ( [C@H] 4 [C@] ( [C@@H] 3O)(C) [C@@] 56 [C@@H] 7C [C@H] ( [C@@] 5(O6)C) [C@] 8(C=CO [C@H] 8O7)O)(C(=O)OC)O)C(=O)OC)OC(=O)C
Section2 = Chembox Properties
C=35|H=44|O=16
MolarMass = 720.714 g/mol
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Section3 = Chembox Hazards
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Azadirachtin is a chemical compound belonging to the limonoids. It is a secondary metabolite present in the Neem tree seeds. The molecular formula is C₃₅H₄₄O₁₆. Azadirachtin is a highly oxidised tetranortriterpenoid which boasts a plethora of oxygen functionality, comprising an enol ether, acetal, hemiacetal, and tetra-substituted oxirane as well as a variety of carboxylic esters. It is classified among the plant secondary metabolites.

Chemistry

Azadirachtin has a complex molecular structure, and as a result the first synthesis was not published for over 22 years after the compound's discovery. The first total synthesis was completed by Steven Ley [Synthesis of Azadirachtin: A Long but Successful Journey ; Gemma E. Veitch, Edith Beckmann, Dr., Brenda J. Burke, Dr., Alistair Boyer, Sarah L. Maslen, Steven V. Ley, Prof. Dr. DOI|10.1002/anie.200703027] in 2007. Both secondary and tertiary hydroxyl groups and tetrahydrofuran ether are present and the molecular structure reveals 16 stereogenic centres, 7 of which are tetrasubstituted. These characteristics explain the great difficulty encountered when trying to produce it by a synthetic approach.

Occurrence

It was initially found to be active as a feeding inhibitor towards the desert locust ("Schistocerca gregaria"), it is now known to affect over 200 species of insect, by acting mainly as an antifeedant and growth disruptor, and as such it possesses considerable toxicity toward insects (LD₅₀("S. littoralis"): 15 ug/g). It fulfills many of the criteria needed for a natural insecticide if it is to replace synthetic compounds. Azadirachtin is biodegradable and shows very low toxicity to mammals, thus being environmentally sound.

This compound is found in the seeds (0.2 to 0.8 percent by weight) of the Neem tree, "Azadirachta indica" (hence the prefix aza does not imply an aza compound, but refers to the Latin species name). Many more compounds, related to Azadirachtin, are present in the seeds as well as in the leaves and the bark of the Neem tree which also show strong biological activities among various pest insects [Senthil-Nathan, S., Kalaivani, K., Murugan, K., Chung, .G. 2005. The toxicity and physiological effect of neem limonoids on Cnaphalocrocis medinalis (Guenée) the rice leaffolder. [http://dx.doi.org/10.1016/j.pestbp.2004.10.004] ] [Senthil-Nathan, S., Kalaivani, K., Murugan, K., Chung, P.G., 2005 Effects of neem limonoids on malarial vector Anopheles stephensi Liston (Diptera: Culicidae). [http://dx.doi.org/10.1016/j.actatropica.2005.07.002] Effects of these preparations on beneficial arthropods are generally considered to be minimal. Some laboratory and field studies have found neem extracts to be compatible with biological control.

ee also

*Neem
*Neem cake
*Neem oil

References

External links

* [http://extoxnet.orst.edu/pips/azadirac.htm Extoxnet]
* [http://www.pakissan.com/english/allabout/horticulture/neem.wonder.tree.shtml Neem: The wonder tree]
* [http://www.plasmaneem.com/about-neem.htm The Wonder of Azadirachtin]