45656

Rotenone

PESTANAL^®, analytical standard

• Empirical Formula (Hill Notation): C₂₃H₂₂O₆
• CAS Number: 83-79-4
• Molecular Weight: 394.42
• UNSPSC Code: 41116107
• NACRES: NA.24
• PubChem Substance ID: 329756870
• EC Number: 201-501-9
• Beilstein/REAXYS Number: 6773081
• MDL number: MFCD09025614

Properties

• Product Name: Rotenone, PESTANAL^®, analytical standard
• InChI key: JUVIOZPCNVVQFO-HBGVWJBISA-N
• 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
• SMILES string: COc1cc2OCC3Oc4c5C[C@@H](Oc5ccc4C(=O)C3c2cc1OC)C(C)=C
• grade: analytical standard
• 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
• Quality Level: 100

Description

Application

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

Rotenone may be used as an analytical reference standard for the quantification of the analyte in raw honey samples[1] and biological samples[2] using different chromatography techniques.

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).

General description

Rotenone is a contact insecticide and a slow stomach poison, extremely potent against many insects.[3] It is widely used against Varroa Jacobsoni mite, affecting colonies of honey bees.[1]

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

Safety Information

• 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
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk: WGK 3
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges