R8875

Rotenone

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

• Fórmula empírica (notación de Hill): C₂₃H₂₂O₆
• Número de CAS: 83-79-4
• Peso molecular: 394.42
• Beilstein: 6773081
• Número CE: 201-501-9
• Número MDL: MFCD09025614
• Código UNSPSC: 12352202
• ID de la sustancia en PubChem: 24278683
• NACRES: NA.77

Propiedades

• product name: Rotenone, ≥95%
• Análisis: ≥95%
• bp: 210-220 °C/0.5 mmHg (lit.)
• mp: 159-164 °C (lit.)
• cadena SMILES: 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
• Clave InChI: JUVIOZPCNVVQFO-HBGVWJBISA-N

Descripción

Descripción general

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.

Aplicación

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

Acciones bioquímicas o fisiológicas

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).

Nota de preparación

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.

Otras notas

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

Información de seguridad

• Pictogramas: GHS06,GHS09
• Palabra de señalización: Danger
• Frases de peligro: H300 + H330,H315,H319,H335,H410
• Consejos de prudencia: P260 - P264 - P273 - P302 + P352 - P304 + P340 + P310 - P305 + P351 + P338
• Clasificaciones de peligro: Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Órganos de actuación: Respiratory system
• Código de clase de almacenamiento: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Clase de riesgo para el agua (WGK): WGK 3