R8875

Rotenone

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

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

Propriedades

• Nome do produto: Rotenone, ≥95%
• Ensaio: ≥95%
• p.e.: 210-220 °C/0.5 mmHg (lit.)
• pf: 159-164 °C (lit.)
• cadeia de caracteres 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
• chave InChI: JUVIOZPCNVVQFO-HBGVWJBISA-N

Descrição

Descrição geral

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.

Aplicação

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

Ações bioquímicas/fisiológicas

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).

Nota de preparo

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.

Outras notas

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

Informações de segurança

• Pictogramas: GHS06,GHS09
• Palavra indicadora: Danger
• Frases de perigo: H300 + H330,H315,H319,H335,H410
• Declarações de precaução: P260 - P264 - P273 - P302 + P352 - P304 + P340 + P310 - P305 + P351 + P338
• Classificações de perigo: Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Órgãos-alvo: Respiratory system
• Código de classe de armazenamento: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Classe de risco de água (WGK): WGK 3