Rotenone CAS: 83-79-4
MF: C23H22O6
MW: 394.42
A mitochondrial toxin and a potent, reversible, and competitive inhibitor of complex I of the respiratory chain.

Rotenone (CAS 83-79-4)

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Synonym: Paraderil; Dactinol; Rotocide
Application: A mitochondrial toxin and a potent, reversible, and competitive inhibitor of complex I of the respiratory chain
CAS Number: 83-79-4
Purity: ≥97%
Molecular Weight: 394.42
Molecular Formula: C23H22O6
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Rotenone is a mitochondrial electron transport inhibitor, which specifically inhibits NAD-linked substrate oxidation of NADH dehydrogenase with an EC50=10 pmol/mg. It is known that this interference of the electron transport chain occurs from complex I to ubiquinone, similarly to amytal. Studies indicate that Rotenone inhibits mammalian cell proliferation, via suppressing microtubule assembly by binding to tubulin. Rotenone can inhibit the effects of N-methyl-4-phenylpyridinium on mitochondrial swelling and cytochrome c release. Rotenone is an inhibitor of NDUFS.


References

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12. Jin, J., et al. 2007. BMC Neurosci. 8: 67. PMID: 17705834
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Physical State :
Solid
Derived From :
Lonchocarpus sp. or Derris sp.
Solubility :
Soluble in ethanol (1:300), chloroform (1:3), ether (1:200), and DMSO (100 mM). Insoluble in water.
Storage :
Store at room temperature
Melting Point :
159-164° C
Boiling Point :
210-220° C at 0.5 mmHg
Density :
1.27 g/cm3 at 20° C
Refractive Index :
n20D 1.59 (Predicted)
Optical Activity :
α20/D -114°±2°, c = 1 in CHCl3; α25/D -120° in 1.38 g/100 ml chloroform
IC50 :
mitochondrial electron transport chain: IC50 = 1.7 - 2.2 µM; NADH oxidation : IC50 = 3.4 nM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
DJ2800000
PubChem CID :
6758
Merck Index :
14: 8271
MDL Number :
MFCD09025614
EC Number :
201-501-9
Beilstein Registry :
6773081
SMILES :
CC(=C)[[email protected]]1CC2=C(O1)C=CC3=C2O[[email protected]@H]4COC5=CC(=C(C=C5[[email protected]@H]4C3=O)OC)OC

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Rotenone  Product Citations

See how others have used Rotenone. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 10 total

PMID: # 31091796  Guerra, F.|Girolimetti, G.|Beli, R.|Mitruccio, M.|Pacelli, C.|Ferretta, A.|Gasparre, G.|Cocco, T.|Bucci, C.| et al. 2019. Cells. 8:

PMID: # 31302317  Kim, J. et al. 2019. Phytomedicine. 63: 153019.

PMID: # 28082109  Hartman, JH.|Miller, GP.|Caro, AA.|Byrum, SD.|Orr, LM.|Mackintosh, SG.|Tackett, AJ.|MacMillan-Crow, LA.|Hallberg, LM.|Ameredes, BT.|Boysen, G.| et al. 2017. Toxicology. 378: 114-124.

PMID: # 28963531  Ahn, H. et al. 2017. Sci Rep. 7: 12409.

PMID: # 25461402  Ahn, H. et al. 2015. Cytokine. 71: 223-31.

PMID: # 23939289  Son, MJ. et al. 2013. Int. J. Biochem. Cell Biol. 45: 2512-8.

PMID: # 22987451  Porceddu, M. et al. 2012. Toxicol. Sci. 129: 332-45.

PMID: # 30209319  Sci Rep. 8: 13659.

PMID: # 31875549  Cell Rep. 29: 4407-4421.e5.

PMID: # 27423466  Lee, J. et al. Cell. Immunol. 306-307: 53-60.

Citations 1 to 10 of 10 total
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