Azadirachtin

Base Information

• Chemical Name: Azadirachtin
• CAS No.: 11141-17-6
• Deprecated CAS: 55890-15-8,95507-01-0,61812-38-2,176087-48-2,189284-01-3,61812-38-2,95507-01-0
• Molecular Formula: C₃₅H₄₄O₁₆
• Molecular Weight: 720.725
• Hs Code.: 13021920
• UNII: O4U1SAF85H
• ChEMBL ID: CHEMBL509309
• DSSTox Substance ID: DTXSID0037497
• Metabolomics Workbench ID: 28733
• Nikkaji Number: J649.024G
• Wikidata: Q793471
• Wikipedia: Azadirachtin
• Mol file: 11141-17-6.mol

Synonyms:azadirachtin;azadirachtin A;azadyrachtin;bioneem;neemix

Chemical Property of Azadirachtin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 159 °C
• Refractive Index: 1.623
• Boiling Point: 792.413 °C at 760 mmHg
• PKA: 9.78±0.70(Predicted)
• Flash Point: 244.841 °C
• PSA: 212.04000
• Density: 1.51 g/cm³
• LogP: -0.20310
• Storage Temp.: −20°C
• Solubility.: DMSO (Sparingly), Methanol (Slightly)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 10
• Exact Mass: 720.26293531
• Heavy Atom Count: 51
• Complexity: 1660

Purity/Quality:

99% ^*data from raw suppliers

Azadirachtin ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 22-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Other Insecticides
• Canonical SMILES: CC=C(C)C(=O)OC1CC(C2(COC3C2C14COC(C4C(C3O)(C)C56C7CC(C5(O6)C)C8(C=COC8O7)O)(C(=O)OC)O)C(=O)OC)OC(=O)C
• Isomeric SMILES: C/C=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
• Description: Kernel extracts from the Indian neem tree (Azadirachta indica) have insecticidal and insect-repellent properties. The key active ingredient is azadirachtin, a nortriterpenoid that exhibits insect growth regulator effects but no adulticidal activity.
• Uses: Azadirachtin is a tetranortriterpinoid isolated from the seeds of the neem tree. Highly active insect feeding deterrent and growth regulator.It is used experimentally as insect control agent. Azadiractin is extracted from the neem tree (Azadirachta indica). It is the principal active ingredient of extracts of neem. Neem extracts and pure azadirachtin are used to control whitefly, leaf miners and other pests including pear psylla.

Technology Process of Azadirachtin

There total 6 articles about Azadirachtin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

23-α,β-acetoxy-22,23-dihydroazadirachtin (122437-48-3,125278-90-2,130932-04-6) → azadirachtin (11141-17-6,95507-03-2)

Guidance literature:

at 175 ℃; for 0.0833333h; under 0.002 Torr;

DOI:10.1016/S0040-4039(00)82888-9

Reference yield: 85.0%

C41H50O16Se → azadirachtin (11141-17-6,95507-03-2)

Guidance literature:

With pyridine; dihydrogen peroxide; In 1,2-dichloro-ethane; at 0 ℃; for 0.166667h;

DOI:10.1021/ol7027898

Reference yield: 67.0%

22,23-dihydro-23-β-thiophenoxyazadirachtin (167101-22-6) → azadirachtin (11141-17-6,95507-03-2)

Guidance literature:

22,23-dihydro-23-β-thiophenoxyazadirachtin; With 3,3-dimethyldioxirane; In dichloromethane; at -78 - 20 ℃;

In dichloromethane; toluene; Further stages.; Heating;

DOI:10.1002/anie.200703028

upstream raw materials:

23-α,β-acetoxy-22,23-dihydroazadirachtin

22,23-dihydro-23-β-thiophenoxyazadirachtin

Downstream raw materials:

22-α-bromo-22,23-dihydro-23-α,β-ethoxyazadirachtin

C₃₇H₄₉BrO₁₇

22-α-bromo-22,23-dihydro-23-β-ethoxyazadirachtin

methyl-(1S,2R,3R,5R,6S,7S,8R,11R,15S,17R,18R,1'S,5'R,7'S,9'R,11'S)-3,7,17-trihydroxy-6,9'-dimethyl-15-<(2-methyl-1-oxo-2-butenyl)oxy>-12-oxospiro<<4,9,14>trioxapentacyclo<9.3.3.1^1,8.0^2,4.0^11,15> octadecane-5,8'<4,6,10>trioxatetracyclo...

Refernces

CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA INDICA (Part 3) REACTIONS ON THE C-22,23 ENOL ETHER DOUBLE BOND OF AZADIRACHTIN AND CONVERSION TO 22,23-DIHYDRO-23-&β-METHOXYAZADIRACHTIN.

10.1016/S0040-4039(00)82888-9

The research investigates the chemical modifications of azadirachtin, a potent insect antifeedant and ecdysis inhibitor derived from the neem tree. The study focuses on the reactions of the C-22,23 enol ether double bond in azadirachtin, aiming to develop high-yielding modifications and understand its structure-activity relationships. The researchers discovered that azadirachtin could be converted to 22,23-dihydro-23-P-methoxyazadirachtin through selective bromomethoxylation and subsequent reduction with tri-n-butyltin hydride. They also found that the acetic acid adduct of azadirachtin, when pyrolyzed, yielded azadirachtin in high yield. The antifeedant effects of the synthesized compounds were evaluated on larvae of two major pest species, Spodoptera littoralis and Heliothis virescens, revealing that compounds with greater steric bulk at C-23 and additional bromine substituents at C-22 exhibited reduced antifeedant activity.