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MedKoo Cat#: 584872 | Name: Azadirachtin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Azadirachtin is an insecticide found to disrupted enzyme activity in Drosophila melanogaster and Bombus terrestris.

Chemical Structure

Azadirachtin
Azadirachtin
CAS#11141-17-6

Theoretical Analysis

MedKoo Cat#: 584872

Name: Azadirachtin

CAS#: 11141-17-6

Chemical Formula: C35H44O16

Exact Mass: 720.2629

Molecular Weight: 720.72

Elemental Analysis: C, 58.33; H, 6.15; O, 35.52

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
Azadirachtin; Azatin; Bioneem; Ornazin; Suneem
IUPAC/Chemical Name
1H,7H-Naphtho(1,8-bc:4,4a-c')difuran-5,10a(8H)-dicarboxylic acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-((2-methyl-1-oxo-2-butenyl)oxy)-4-(3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro(2,3-b)oxireno(e)oxepin-1a(2H)-yl)-, dimethyl ester, (2aR-(2aalpha,3beta,4beta(1aR*,2S*,3aS*,6aS*,7S*,7aS*),4abeta,5alpha,7aS*,8beta(E),10beta,10aalpha,10bbeta))-
InChi Key
FTNJWQUOZFUQQJ-NDAWSKJSSA-N
InChi Code
InChI=1S/C35H44O16/c1-8-15(2)24(38)49-18-12-19(48-16(3)36)32(26(39)43-6)13-46-21-22(32)31(18)14-47-34(42,27(40)44-7)25(31)29(4,23(21)37)35-20-11-17(30(35,5)51-35)33(41)9-10-45-28(33)50-20/h8-10,17-23,25,28,37,41-42H,11-14H2,1-7H3/b15-8+/t17-,18+,19-,20+,21-,22-,23-,25+,28+,29-,30+,31+,32+,33+,34+,35+/m1/s1
SMILES Code
O=C([C@@]1(O)OC[C@@]2([C@@H](OC(/C(C)=C/C)=O)C[C@H]3OC(C)=O)[C@]1([H])[C@@]([C@]45[C@](O5)(C)[C@]6([H])[C@]7(O)[C@](OC=C7)([H])O[C@@]4([H])C6)(C)[C@H](O)[C@]8([H])OC[C@@]3(C(OC)=O)[C@]82[H])OC
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 720.72 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Zhang J, Liu H, Sun Z, Xie J, Zhong G, Yi X. Azadirachtin induced apoptosis in the prothoracic gland in Bombyx mori and a pronounced Ca(2+) release effect in Sf9 cells. Int J Biol Sci. 2017 Nov 27;13(12):1532-1539. doi: 10.7150/ijbs.22175. eCollection 2017. PubMed PMID: 29230101; PubMed Central PMCID: PMC5723919. 2: Bezzar-Bendjazia R, Kilani-Morakchi S, Maroua F, Aribi N. Azadirachtin induced larval avoidance and antifeeding by disruption of food intake and digestive enzymes in Drosophila melanogaster (Diptera: Drosophilidae). Pestic Biochem Physiol. 2017 Nov;143:135-140. doi: 10.1016/j.pestbp.2017.08.006. Epub 2017 Aug 5. PubMed PMID: 29183582. 3: Aribi N, Oulhaci MC, Kilani-Morakchi S, Sandoz JC, Kaiser L, Denis B, Joly D. Azadirachtin impact on mate choice, female sexual receptivity and male activity in Drosophila melanogaster (Diptera: Drosophilidae). Pestic Biochem Physiol. 2017 Nov;143:95-101. doi: 10.1016/j.pestbp.2017.09.002. Epub 2017 Sep 5. PubMed PMID: 29183617. 4: Kilani-Morakchi S, Bezzar-Bendjazia R, Ferdenache M, Aribi N. Preimaginal exposure to azadirachtin affects food selection and digestive enzymes in adults of Drosophila melanogaster (Diptera: Drosophilidae). Pestic Biochem Physiol. 2017 Aug;140:58-64. doi: 10.1016/j.pestbp.2017.06.004. Epub 2017 Jun 3. PubMed PMID: 28755695. 5: Oulhaci CM, Denis B, Kilani-Morakchi S, Sandoz JC, Kaiser L, Joly D, Aribi N. Azadirachtin effects on mating success, gametic abnormalities and progeny survival in Drosophila melanogaster (Diptera). Pest Manag Sci. 2018 Jan;74(1):174-180. doi: 10.1002/ps.4678. Epub 2017 Sep 12. PubMed PMID: 28736861. 6: Wang Z, Cheng X, Meng Q, Wang P, Shu B, Hu Q, Hu M, Zhong G. Azadirachtin-induced apoptosis involves lysosomal membrane permeabilization and cathepsin L release in Spodoptera frugiperda Sf9 cells. Int J Biochem Cell Biol. 2015 Jul;64:126-35. doi: 10.1016/j.biocel.2015.03.018. Epub 2015 Apr 4. PubMed PMID: 25849458. 7: Barbosa WF, De Meyer L, Guedes RN, Smagghe G. Lethal and sublethal effects of azadirachtin on the bumblebee Bombus terrestris (Hymenoptera: Apidae). Ecotoxicology. 2015 Jan;24(1):130-42. doi: 10.1007/s10646-014-1365-9. Epub 2014 Oct 10. PubMed PMID: 25300506. 8: Fernandes SR, Barreiros L, Oliveira RF, Cruz A, Prudêncio C, Oliveira AI, Pinho C, Santos N, Morgado J. Chemistry, bioactivities, extraction and analysis of azadirachtin: State-of-the-art. Fitoterapia. 2019 Feb 6;134:141-150. doi: 10.1016/j.fitote.2019.02.006. [Epub ahead of print] Review. PubMed PMID: 30738093. 9: Zhang J, Sun T, Sun Z, Li H, Qi X, Zhong G, Yi X. Azadirachtin acting as a hazardous compound to induce multiple detrimental effects in Drosophila melanogaster. J Hazard Mater. 2018 Oct 5;359:338-347. doi: 10.1016/j.jhazmat.2018.07.057. Epub 2018 Jul 23. PubMed PMID: 30048948. 10: Bezzar-Bendjazia R, Kilani-Morakchi S, Aribi N. Larval exposure to azadirachtin affects fitness and oviposition site preference of Drosophila melanogaster. Pestic Biochem Physiol. 2016 Oct;133:85-90. doi: 10.1016/j.pestbp.2016.02.009. Epub 2016 Mar 2. PubMed PMID: 27742366. 11: Baligar NS, Aladakatti RH, Ahmed M, Hiremath MB. Hepatoprotective activity of the neem-based constituent azadirachtin-A in carbon tetrachloride intoxicated Wistar rats. Can J Physiol Pharmacol. 2014 Apr;92(4):267-77. doi: 10.1139/cjpp-2013-0449. Epub 2014 Jan 9. PubMed PMID: 24708208. 12: Shao X, Lai D, Zhang L, Xu H. Induction of Autophagy and Apoptosis via PI3K/AKT/TOR Pathways by Azadirachtin A in Spodoptera litura Cells. Sci Rep. 2016 Oct 18;6:35482. doi: 10.1038/srep35482. PubMed PMID: 27752103; PubMed Central PMCID: PMC5067515. 13: Shaurub el-SH, Abd El-Meguid A, Abd El-Aziz NM. Quantitative and ultrastructural changes in the haemocytes of Spodoptera littoralis (Boisd.) treated individually or in combination with Spodoptera littoralis multicapsid nucleopolyhedrovirus (SpliMNPV) and azadirachtin. Micron. 2014 Oct;65:62-8. doi: 10.1016/j.micron.2014.04.010. Epub 2014 Apr 30. PubMed PMID: 25041832. 14: Shu B, Wang W, Hu Q, Huang J, Hu M, Zhong G. A COMPREHENSIVE STUDY ON APOPTOSIS INDUCTION BY AZADIRACHTIN IN Spodoptera frugiperda CULTURED CELL LINE Sf9. Arch Insect Biochem Physiol. 2015 Jul;89(3):153-68. doi: 10.1002/arch.21233. Epub 2015 Apr 1. PubMed PMID: 25828604. 15: Xu L, Li S, Ran X, Liu C, Lin R, Wang J. Apoptotic activity and gene responses in Drosophila melanogaster S2 cells, induced by azadirachtin A. Pest Manag Sci. 2016 Sep;72(9):1710-7. doi: 10.1002/ps.4198. Epub 2016 Jan 4. PubMed PMID: 26607310. 16: Soares DG, Godin AM, Menezes RR, Nogueira RD, Brito AM, Melo IS, Coura GM, Souza DG, Amaral FA, Paulino TP, Coelho MM, Machado RR. Anti-inflammatory and antinociceptive activities of azadirachtin in mice. Planta Med. 2014 Jun;80(8-9):630-6. doi: 10.1055/s-0034-1368507. Epub 2014 May 28. PubMed PMID: 24871207. 17: de Castro EA, de Oliveira DA, Farias SA, Gargano R, Martins JB. Structure and electronic properties of azadirachtin. J Mol Model. 2014 Feb;20(2):2084. doi: 10.1007/s00894-014-2084-0. Epub 2014 Feb 9. PubMed PMID: 24509732. 18: Nouri-Ganbalani G, Borzoui E, Abdolmaleki A, Abedi Z, George Kamita S. Individual and Combined Effects of Bacillus Thuringiensis and Azadirachtin on Plodia Interpunctella Hübner (Lepidoptera: Pyralidae). J Insect Sci. 2016 Sep 16;16(1). pii: 95. doi: 10.1093/jisesa/iew086. Print 2016. PubMed PMID: 27638953; PubMed Central PMCID: PMC5026475. 19: Joseph SV. Effects of Insect Growth Regulators on Bagrada hilaris (Hemiptera: Pentatomidae). J Econ Entomol. 2017 Dec 5;110(6):2471-2477. doi: 10.1093/jee/tox264. PubMed PMID: 29040567. 20: Lin T, Liu Q, Chen J. Identification of differentially expressed genes in Monochamus alternatus digested with azadirachtin. Sci Rep. 2016 Sep 15;6:33484. doi: 10.1038/srep33484. PubMed PMID: 27629396; PubMed Central PMCID: PMC5024161.

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