A limonoid with diverse biological activities
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Azadiradione

Item No. 37063

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5α,7α,13α,17α)-7-(acetyloxy)-21,23-epoxy-4,4,8-trimethyl-24-norchola-1,14,20,22-tetraene-3,16-dione
CAS Number
26241-51-0
Molecular Formula
C28H34O5
Formula Weight
450.6
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Sparingly soluble: 1-10 mg/mlMethanol: Slightly soluble: 0.1-1 mg/ml
SMILES
C[C@]12C([C@]([C@]3([H])C4=COC=C4)(CC[C@]1([H])[C@@]5([C@@](C(C)(C(C=C5)=O)C)([H])C[C@H]2OC(C)=O)C)C)=CC3=O
InChi Code
InChI=1S/C28H34O5/c1-16(29)33-23-14-20-25(2,3)22(31)8-11-26(20,4)19-7-10-27(5)21(28(19,23)6)13-18(30)24(27)17-9-12-32-15-17/h8-9,11-13,15,19-20,23-24H,7,10,14H2,1-6H3/t19-,20+,23-,24-,26-,27-,28-/m1/s1
InChi Key
KWAMDQVQFVBEAU-HMWIRDDCSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $303

    Add

    5 mg

    $908

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    Azadiradione is a limonoid that has been found in A. indica and has diverse biological activities.1,2,3,4,5 It inhibits heparin-induced tau aggregation by 54.2% in a cell-free assay when used at a concentration of 400 µM.2 Azadiradione inhibits the tautomerase activity of human, P. falciparum, and P. yoelii migration inhibitory factor (MIF; IC50s = 35.2, 45.6, and 43 µM, respectively).1 It is cytotoxic to HL-60 leukemia and SK-BR-3 breast cancer cells (IC50s = 14.7 and 15.9 µM, respectively) but not A549 lung, AZ-521 stomach, or CRL-1579 melanoma cells (IC50s = >20 µM for all).3 Azadiradione (10 mg/kg) decreases the mutant huntingtin aggregate load in the cortex, striatum, and hippocampus, improves motor function, and increases lifespan in the R6/2 transgenic mouse model of Huntington’s disease.4 It increases the levels of heat shock factor 1 (Hsf1), heat shock protein 70 (Hsp70), and ubiquitin-protein ligase E3A (Ube3a) in the mouse cortex and striatum in the same model. Azadiradione (10 mg/kg) also reduces blood glucose levels and α-amylase activity, as well as serum triglyceride and HDL levels, in a rat model of diabetes induced by streptozotocin (Item No. 13104).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Alam, A., Haldar, S., Thulasiram, H.V., et al. Novel anti-inflammatory activity of epoxyazadiradione against macrophage migration inhibitory factor: Inhibition of tautomerase and proinflammatory activities of macrophage migration inhibitory factor. The Journal of Biological Chemisty 287(29), 24844-24861 (2012).

    2. Gorantla, N.V., Das, R., Chidambaram, H., et al. Basic limonoid modulates chaperone-mediated proteostasis and dissolve Tau fibrils. Sci. Rep. 10(1), 4023 (2020).

    3. Kikuchi, T., Ishii, K., Noto, T., et al. Cytotoxic and apoptosis-inducing activities of limonoids from the seeds of Azadirachta indica (neem). J. Nat. Prod. 74(4), 866-870 (2011).

    4. Singh, B.K., Vatsa, N., Nelson, V.K., et al. Azadiradione restores protein quality control and ameliorates the disease pathogenesis in a mouse model of Huntington’s disease. Mol. Neurobiol. 55(8), 6337-6346 (2018).

    5. Ramkumar, S., Thulasiram, H.V., and RaviKumar, A. Improvement in serum amylase and glucose levels in diabetic rats on oral administration of bisdemethoxycurcumin from Curcuma longa and limonoids from Azadirachta indica. J. Food Biochem. 45(4), e13674 (2021).