R8875

Rotenone

≥95% (HPLC), powder, NADH-CoQ reductase inhibitor

• Empirical Formula (Hill Notation): C₂₃H₂₂O₆
• CAS Number: 83-79-4
• Molecular Weight: 394.42
• Beilstein: 6773081
• EC Number: 201-501-9
• MDL number: MFCD09025614
• UNSPSC Code: 12352202
• PubChem Substance ID: 24278683
• NACRES: NA.77

Properties

• Product Name: Rotenone, ≥95%
• Quality Level: 200
• 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

Description

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

Inhibitor of mitochondrial electron transport.

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. The primary mechanism of action of rotenone is complex I inhibition, followed by the generation of oxidative stress and oxidative damage. Because rotenone is lipophilic, it readily penetrates the brain, where it attaches to and inhibits mitochondrial complex I of electron chain transport (ETC).

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

Safety Information

• Pictograms: GHS06,GHS09
• Signal Word: Danger
• Hazard Statements: H300 + H330,H315,H319,H335,H410
• Precautionary Statements: P260 - P264 - P273 - P302 + P352 - P304 + P340 + P310 - P305 + P351 + P338
• 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