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Azadirachtin
From Wikipedia, the free encyclopedia
| Azadirachtin | |
|---|---|
 |
|
| General | |
| Systematic name | ? |
| Other names | ? |
| Molecular formula | C35H44O16 |
| SMILES | ? |
| Molar mass | 720.69936 g/mol |
| Appearance | ? |
| CAS number | [11141-17-6] |
| Properties | |
| Density and phase | ? g/cm3, ? |
| Solubility in water | ? g/100 ml (?°C) |
| Melting point | ?°C (? K) |
| Boiling point | ?°C (? K) |
| Acidity (pKa) | ? |
| Basicity (pKb) | ? |
| Chiral rotation [α]D | ?° |
| Viscosity | ? cP at ?°C |
| Structure | |
| Molecular shape | ? |
| Coordination geometry |
? |
| Crystal structure | ? |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | ?°C |
| R/S statement | R: ? S: ? |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Other anions | ? |
| Other cations | ? |
| Related ? | ? |
| Related compounds | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references |
|
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.
Additionally, both secondary and tertiary hydroxyl groups and tetrahydrofuran ether are present. Inspection of 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. 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. It fulfils 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 of the Neem tree (0.2 to 0.8 percent by weight). 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. Azadirachtin is the only correct name for this compound e.g. azadirachtin A is incorrect.