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R8875

Sigma-Aldrich

Rotenone

≥95%

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Empirical Formula (Hill Notation):
C23H22O6
CAS Number:
Molecular Weight:
394.42
Beilstein:
6773081
EC Number:
MDL number:
PubChem Substance ID:
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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This Item
SMB0060445656557368
Rotenone ≥95%

Sigma-Aldrich

R8875

Rotenone

Bakuchiol ≥95%

Sigma-Aldrich

SMB00604

Bakuchiol

Rotenone PESTANAL®, analytical standard

Supelco

45656

Rotenone

Rotenone A mitochondrial toxin and a potent, reversible, and competitive inhibitor of complex I (NADH-CoQ reductase) of the respiratory chain.

Sigma-Aldrich

557368

Rotenone

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

bp

210-220 °C/0.5 mmHg (lit.)

bp

-

bp

210-220 °C/0.5 mmHg (lit.)

bp

-

mp

159-164 °C (lit.)

mp

-

mp

159-164 °C (lit.)

mp

-

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.

Pictograms

Skull and crossbonesEnvironment

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


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