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Azadirachtin

CAS# 11141-17-6

Azadirachtin

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Chemical structure

Azadirachtin

3D structure

Chemical Properties of Azadirachtin

Cas No. 11141-17-6 SDF Download SDF
PubChem ID 5281303 Appearance White powder
Formula C35H44O16 M.Wt 720.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Azadirachtin A; Azatin
Solubility Soluble in acetonitrile, ethyl acetate and methan
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
Standard InChIKey FTNJWQUOZFUQQJ-NDAWSKJSSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Azadirachtin

The bark of Azadirachta Indica

Biological Activity of Azadirachtin

DescriptionAzadirachtin has antifungal activity, it used as insecticides.
TargetsAntifection
In vitro

Botanical Insecticides in the Twenty-First Century-Fulfilling Their Promise?[Pubmed: 31594414]

Annu Rev Entomol. 2019 Oct 8.


METHODS AND RESULTS:
Academic interest in plant natural products with insecticidal properties has continued to grow in the past 20 years, while commercialization of new botanical insecticides and market expansion of existing botanicals has lagged considerably behind. Insecticides based on pyrethrum and neem (Azadirachtin) continue to be standard bearers in this class of pesticides, but globally, their increased presence is largely a consequence of introduction into new jurisdictions. Insecticides based on plant essential oils are just beginning to emerge as useful plant protectants. Some countries (such as Turkey, Uruguay, the United Arab Emirates, and Australia) have relaxed regulatory requirements for specific plant extracts and oils, while in North America and the European Union, stricter requirements have slowed progress toward commercialization of new products.
CONCLUSIONS:
Botanicals are likely to remain niche products in many agricultural regions and may have the greatest impact in developing countries in tropical regions where the source plants are readily available and conventional products are both expensive and dangerous to users.

In Vitro Activity of Neem (Azadirachta indica) Oil on Growth and Ochratoxin A Production by Aspergillus carbonarius Isolates.[Pubmed: 31590398]

Toxins (Basel). 2019 Oct 5;11(10). pii: E579.

Aspergillus carbonarius is a saprobic filamentous fungus, food spoiling fungus and a producer of ochratoxin A (OTA) mycotoxin.
METHODS AND RESULTS:
In this study, the in vitro antifungal activity of neem oil (0.12% p/p of Azadirachtin) was evaluated against the growth of six strains of A. carbonarius and the production of OTA. Four different concentrations of neem oil were tested in addition to three incubation times. Only the concentration of 0.3% of neem oil inhibited more than 95% of the strain's growth (97.6% ± 0.5%), while the use of 0.5% and 1.0% of neem oil showed lower antifungal activity, 40.2% ± 3.1 and 64.7% ± 1.1, respectively. There was a complete inhibition of OTA production with 0.1% and 0.3% neem oil in the four strains isolated in the laboratory from grapes.
CONCLUSIONS:
The present study shows that neem essential oil can be further evaluated as an auxiliary method for the reduction of mycelial growth and OTA production.

Azadirachtin Dilution Calculator

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Preparing Stock Solutions of Azadirachtin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.3875 mL 6.9377 mL 13.8754 mL 27.7508 mL 34.6885 mL
5 mM 0.2775 mL 1.3875 mL 2.7751 mL 5.5502 mL 6.9377 mL
10 mM 0.1388 mL 0.6938 mL 1.3875 mL 2.7751 mL 3.4688 mL
50 mM 0.0278 mL 0.1388 mL 0.2775 mL 0.555 mL 0.6938 mL
100 mM 0.0139 mL 0.0694 mL 0.1388 mL 0.2775 mL 0.3469 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Azadirachtin

DnaJ homolog subfamily A member1 (DnaJ1) is a newly discovered anti-apoptotic protein regulated by azadirachtin in Sf9 cells.[Pubmed:29843605]

BMC Genomics. 2018 May 29;19(1):413.

BACKGROUND: Azadirachtin, one of the most promising botanical insecticides, has been widely used for pest control. Azadirachtin induces apoptosis in insect cell lines, including Sf9, SL-1 and BTI-Tn-5B1-4. Mitochondrial and lysosomal pathways are likely involved in the Azadirachtin-induced apoptosis, however, detailed molecular mechanisms remain largely undefined. RESULTS: Azadirachtin-induced apoptosis in Sf9 cells was verified by morphological observation, Hoechst 33258 staining, and a Caspase-3-based analysis. Comparative two-dimensional gel electrophoresis (2-DE) coupled with a linear ion trap quadrupole (LTQ)-MS/MS analysis identified 12 prominent, differentially expressed proteins following Azadirachtin treatment. These differentially expressed genes are involved in regulating cytoskeleton development, signal transduction, gene transcription, and cellular metabolism. Knockdown gene expression of a gene encoding a DnaJ homolog enhanced apoptosis induced by Azadirachtin in Sf9 cells. CONCLUSION: Azadirachtin treatment induces apoptosis in Sf9 cells and affects expression of multiple genes with functions in cytoskeleton development, signal transduction, gene regulation, and cellular metabolisms. Azadirachtin induces apoptosis at least partially by down-regulation of Sf-DnaJ in Sf9 cells.

Bacterial communities in natural versus pesticide-treated Aphis gossypii populations in North China.[Pubmed:29877631]

Microbiologyopen. 2019 Mar;8(3):e00652.

The cotton-melon aphid, Aphis gossypii Glover, is a worldwide-spreading species, and pesticide-resistant populations are increasing rapidly. In this study, investigations were performed based on Illumina HiSeq sequencing of the 16S rDNA V4 region for the bacterial communities embodied as intracellular symbionts under natural and in pesticide-treated populations of A. gossypii. The results revealed that more than 82% of bacterial communities belonged to the phylum Proteobacteria in which the maximum proportion (53.24%) was of the genus Arsenophonus; Hamiltonella composed 22.31; and 1.37% was of the genus Acinetobacter. The relative abundance of Hamiltonella was obvious, vertically transmitted, divided into two groups, and its infection influenced the bacterial communities in A. gossypii. Symbiont density and composition were changed in samples tested on different days. Azadirachtin and phoxim influenced on the composition of bacterial communities. Different biomarkers were used for pesticide-treated samples with LEfSe results. These findings will increase awareness regarding bacterial communities in naturally occurring populations of A. gossypii and pave the way to study the relationship between symbionts and pesticide resistance.

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