A rotenoid with diverse biological activities
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Isomer(s)
13995Rotenone
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(−)-Deguelin

Item No. 10010706

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
13,13aS-dihydro-9,10-dimethoxy-3,3-dimethyl-3H-[1]benzopyrano[3,4-b]pyrano[2,3-h][1]benzopyran-7(7aS)-one
CAS Number
522-17-8
Synonyms
  • (−)-cis-Deguelin
Molecular Formula
C23H22O6
Formula Weight
394.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) 1:4: 0.33 mg/mlDMSO: 25 mg/mlEthanol: Insoluble*
λmax
238, 252, 270, 297 nm
SMILES
COC1=CC2=C(C=C1OC)OC[C@]3([H])[C@@]2([H])C(C(C=CC4=C5C=CC(C)(C)O4)=C5O3)=O
InChi Code
InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1
InChi Key
ORDAZKGHSNRHTD-UXHICEINSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    (−)-Deguelin is a rotenoid that has been found in T. vogelii and has diverse biological activities.1,2,3,4 It inhibits mitochondrial complex I, also known as NADH dehydrogenase, activity in bovine heart electron transport particles and phorbol 12-myristate 13-acetate-induced ornithine decarboxylase (ODC) activity in MCF-7 breast cancer cells (IC50s = 6.9 and 11 nM, respectively).2 (−)-Deguelin (100 nM) induces apoptosis in MCF-7 and SK-BR-3 breast cancer cells.3 It induces mortality in adult bruchid beetles (C. maculatus) when used at concentrations ranging from 10 to 500 ppm.1 (−)-Deguelin (6 mg/kg) induces nigrostriatal dopaminergic degeneration in rats.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Belmain, S.R., Amoah, B.A., Nyirenda, S.P., et al. Highly variable insect control efficacy of Tephrosia vogelii chemotypes. J. Agric. Food Chem. 60(40), 10055-10063 (2012).

    2. Fang, N., and Casida, J.E. Anticancer action of cubé insecticide: Correlation for rotenoid constituents between inhibition of NADH: Ubiquinone oxidoreductase and induced ornithine decarboxylase activities. Proc. Natl. Acad. Sci. USA 95(7), 3380-3384 (1998).

    3. Peng, X.H., Karna, P., O'Regan, R.M., et al. Down-regulation of inhibitor of apoptosis proteins by deguelin selectively induces apoptosis in breast cancer cells. Mol. Pharmacol. 71(1), 101-111 (2007).

    4. Caboni, P., Sherer, T.B., Zhang, N., et al. Rotenone, deguelin, their metabolites, and the rat model of Parkinson’s disease. Chem. Res. Toxicol. 17(11), 1540-1548 (2004).