An azadirachtin with diverse biological activities
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Azadirachtin B

Item No. 29569

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-octahydro-3,8-dihydroxy-4-methyl-10-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-7H,8H-furo[3′,4′:4,4a]naphtho[1,8-bc]furan-5,10a(1H)-dicarboxylic acid, 5,10a-dimethyl ester
CAS Number
106500-25-8
Synonyms
  • Deacetylazadirachtinol
  • 3-Tigloylazadirachtol
Molecular Formula
C33H42O14
Formula Weight
662.7
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: slightly solubleDMSO: slightly solubleMethanol: slightly soluble
SMILES
O=C(OC)[C@H]1OC[C@]23[C@@H](O)C[C@@H](OC(/C(C)=C/C)=O)[C@]4(C(OC)=O)[C@]2([H])[C@](OC4)([H])[C@@H](O)[C@@](C)([C@]56[C@@](C)(O6)[C@]7([H])[C@](C=CO8)(O)[C@]8([H])O[C@@]5([H])C7)[C@@]31[H]
InChi Code
InChI=1S/C33H42O14/c1-7-14(2)24(36)45-17-11-16(34)30-12-44-20(25(37)40-5)21(30)28(3,23(35)19-22(30)31(17,13-43-19)26(38)41-6)33-18-10-15(29(33,4)47-33)32(39)8-9-42-27(32)46-18/h7-9,15-23,27,34-35,39H,10-13H2,1-6H3/b14-7+/t15-,16+,17-,18+,19-,20+,21+,22-,23-,27+,28+,29+,30-,31+,32+,33+/m1/s1
InChi Key
USRBWQQLHKQWAV-ZGKQVQOISA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Azadirachtin B is an azadirachtin that has been found in the neem tree, A. indica, and has diverse biological activities, including insecticidal, nematocidal, anticancer, and osteogenic properties.1,2,3,4,5 It has antifeedant activity against P. xylostella third instar larvae when used at a concentration of 3 mg/ml and induces mortality with an LC50 of 1.03 mg/ml.2 It induces mortality in M. incognita second instar larvae with an LD50 value of 125.8 ppm.3 Azadirachtin B (780 nmol in the drinking water) reduces the number of papillomas formed on mouse skin in a model of skin carcinogenesis induced by peroxynitrite and phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) but is not cytotoxic to HL-60, A549, AZ521, SK-BR-3, or CRL1579 cancer cells (IC50s = >20 µM for all).4,5 It induces osteoblast differentiation and increases the rate of osteoblast proliferation in primary calvarial osteoblast cells when used at concentrations of 100 pM and 10 nM but not 1 pM, 1 µM, or 100 µM.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kushwaha, P.K., Khedgikar, V., Haldar, S., et al. Azadirachta indica triterpenoids promote osteoblast differentiation and mineralization in vitro and in vivo. Bioorg. Med. Chem. Lett. 26(15), 3719-3724 (2016).

    2. Zhang, Z., Cheng, D., and Xu, H. A comparative study on bioactivity of azadirachtin A and azadirachtin B. Zhiwu Baohu 33(3), 80-82 (2007).

    3. Sinha, S., Chakraborty, U., Mishra, S.D., et al. Bioactivity of normal and UV exposed azadirachtins A, B and H against the root-knot nnematode, Meloidogyne incognita. Indian J. Nemat. 35(2), 183-186 (2005).

    4. Akihisa, T., Noto, T., Takahashi, A., et al. Melanogenesis inhibitory, anti-inflammatory, and chemopreventive effects of limonoids from the seeds of Azadirachta indicia A. juss. (neem). J. Oleo. Sci. 58(11), 581-594 (2009).

    5. 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).