Rotenone

Pricing Availability Delivery Time Qty
Cat.No. 3616 - Rotenone | C23H22O6 | CAS No. 83-79-4
Description: Inhibits complex I of the mitochondrial electron transport chain
Chemical Name: (2R,6aS,12aS)-1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
Purity: ≥95% (HPLC)
Datasheet
Citations (1)
Literature

Biological Activity

Mitochondrial electron transport chain inhibitor (IC50 = 1.7 - 2.2 μM at complex I). Inhibits NADH oxidation by cardiac sarcoplasmic reticulum (IC50 = 3.4 nM). Commonly used pesticide and induces Parkinsonism in animal models. May also inhibit autophagy induction; blocks lysosomal degradation of autophagic vacuoles. Cell-permeable and brain penetrant.

Technical Data

M. Wt 394.42
Formula C23H22O6
Storage Store at RT
Purity ≥95% (HPLC)
CAS Number 83-79-4
PubChem ID 6758
InChI Key JUVIOZPCNVVQFO-HBGVWJBISA-N
Smiles C=[C@](C)[C@@H](C5)OC4=C5C(O3)=C(C=C4)C([C@@]([C@@]3([H])CO2)([H])C1=C2C=C(OC)C(OC)=C1)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 39.44 100
ethanol 1.97 5

Preparing Stock Solutions

The following data is based on the product molecular weight 394.42. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.54 mL 12.68 mL 25.35 mL
5 mM 0.51 mL 2.54 mL 5.07 mL
10 mM 0.25 mL 1.27 mL 2.54 mL
50 mM 0.05 mL 0.25 mL 0.51 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Cherednichenko et al (2004) NADH oxidase activity of rat cardiac sarcoplasmic reticulum regulates calcium-induced calcium release. Circ.Res. 94 478 PMID: 14699012

Uversky (2004) Neurotoxicant-induced animal models of Parkinson's disease: understanding the role of rotenone, maneb and paraquat in neurodegeneration. Cell Tissue Res. 318 225 PMID: 15258850

Gomez et al (2007) Pesticides and impairment of mitochondrial function in relation with the parkinsonian syndrome. Front.Biosci. 12 1079 PMID: 17127363

Mader et al (2012) Rotenone inhibits autophagic flux prior to inducing cell death. ACS Chem.Neurosci. 3 1063 PMID: 23259041


If you know of a relevant reference for Rotenone, please let us know.

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Keywords: inhibitors inhibits complex I mitochondrial electron transport chain Oxidative phosphorylation parkinson's parkinsons parkinsonism complex I Oxidative Phosphorylation

1 Citation for Rotenone

Citations are publications that use Tocris products. Selected citations for Rotenone include:

Juliana et al (2012) Non-transcriptional priming and deubiquitination regulate NLRP3 inflammasome activation. Leukemia 287 36617 PMID: 22948162


Do you know of a great paper that uses Rotenone from Tocris? If so please let us know.

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New Product Guide (Spring/Summer 2017)

Our new product guide highlights over 130 new products added to the Tocris Bioscience range during the first half of 2017.

  • 7-TM Receptors
  • Enzymes
  • Enzyme-Linked Receptors
  • Ion Channels
  • Nuclear Receptors
  • Transporters
  • Apoptosis
  • Cell Metabolism
  • Epigenetics
  • Fluorescent Imaging
  • Signal Transduction
  • Stem Cells

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