45656

Rotenone

PESTANAL^®, analytical standard

• Formula empirica (notazione di Hill): C₂₃H₂₂O₆
• Numero CAS: 83-79-4
• Peso molecolare: 394.42
• UNSPSC Code: 41116107
• NACRES: NA.24
• PubChem Substance ID: 329756870
• EC Number: 201-501-9
• Beilstein/REAXYS Number: 6773081
• MDL number: MFCD09025614

Proprietà

• grade: analytical standard
• Quality Segment: 100
• product line: PESTANAL^®
• shelf life: limited shelf life, expiry date on the label
• technique(s): HPLC: suitable, gas chromatography (GC): suitable
• bp: 210-220 °C/0.5 mmHg (lit.)
• mp: 159-164 °C (lit.)
• application(s): agriculture; environmental
• format: neat
• 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

Descrizione

General description

Rotenone is a contact insecticide and a slow stomach poison, extremely potent against many insects. It is widely used against Varroa Jacobsoni mite, affecting colonies of honey bees.

Application

Rotenone may be used as an analytical reference standard for the quantification of the analyte in raw honey samples and biological samples using different chromatography techniques.

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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).

Other Notes

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

Legal Information

PESTANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Informazioni sulla sicurezza

• pictograms: GHS06,GHS09
• signalword: Danger
• hcodes: H300 + H330,H315,H319,H335,H410
• pcodes: 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
• Classe di stoccaggio: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges