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R8875

Sigma-Aldrich

Rotenone

≥95%

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Empirical Formula (Hill Notation):
C23H22O6
CAS Number:
83-79-4
Molecular Weight:
394.42
Beilstein:
6773081
EC Number:
201-501-9
MDL number:
MFCD09025614
PubChem Substance ID:
24278683
NACRES:
NA.77

Assay

≥95%

bp

210-220 °C/0.5 mmHg (lit.)

mp

159-164 °C (lit.)

SMILES string

COc1cc2OCC3Oc4c5C[C@@H](Oc5ccc4C(=O)C3c2cc1OC)C(C)=C

InChI

1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1

InChI key

JUVIOZPCNVVQFO-HBGVWJBISA-N

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General description

Rotenone belongs to the retinoid family. It is naturally present in Leguminosa plants and is considered to be cytotoxic. It is commonly used as an insecticide and a pesticide.

Application

Rotenone has been used:
  • to study its effect on cell proliferation
  • to detect the production of cellular reactive oxygen species in isolated rat forebrain mitochondria
  • to measure mitochondrial enzymatic activity

Biochem/physiol Actions

Rotenone is an inhibitor of mitochondrial electron transport at nicotinamide adenine dinucleotide (NADH):ubiquinone oxidoreductase. It is readily absorbed through the exoskeletons of arthropods, but poorly absorbed cutaneously or from the gastrointestinal tract of mammals. Rotenone acts as a neurotoxic agent which can produce Parkinson-like condition to serve as an animal model for the study of etiology and interventions.

Preparation Note

This product is soluble in DMSO at 0.5 mg/ml. Other sources suggest it can be dissolved in DMSO up to 100 mM, however this has not been verified.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Regulatory Information

农药列管产品

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Metformin decreases glucose oxidation and increases the dependency of prostate cancer cells on reductive glutamine metabolism
Fendt SM, et al.
Cancer Research (2013)
Parkinson's Disease and Movement Disorders, 81-81 (2007)
Jin Bu et al.
Life sciences, 231, 116581-116581 (2019-06-21)
The aims of this study were to investigate the effect of colonic electrical stimulation (CES) on delayed colonic transit in Parkinson's disease (PD) model induced by rotenone and its possible mechanisms. Sprague-Dawley male rats were implanted with a pair of
Loss of Sirt1 promotes prostatic intraepithelial neoplasia, reduces mitophagy, and delays PARK2 translocation to mitochondria
Di SG, et al.
The American Journal of Pathology, 185(1), 266-279 (2015)
Overexpression of TFAM or twinkle increases mtDNA copy number and facilitates cardioprotection associated with limited mitochondrial oxidative stress
Ikeda M, et al.
PLoS ONE, 10(3), e0119687-e0119687 (2015)
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