CRM38703

Rotenone

certified reference material, TraceCERT^®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

• Empirical Formula (Hill Notation): C₂₃H₂₂O₆
• CAS Number: 83-79-4
• Molecular Weight: 394.42
• Beilstein: 6773081
• MDL number: MFCD09025614
• UNSPSC Code: 41116107
• NACRES: NA.24

Properties

• grade: certified reference material; TraceCERT^®
• Quality Level: 300
• product line: TraceCERT^®
• shelf life: limited shelf life, expiry date on the label
• manufacturer/tradename: Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
• bp: 210-220 °C/0.5 mmHg (lit.)
• mp: 159-164 °C (lit.)
• storage temp.: 2-8°C
• 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

This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO 17034. This CRM is traceable to primary material from an NMI, e.g. NIST or NMIJ.
Certified content by quantitative NMR incl. uncertainty and expiry date are given on the certificate.
Download your certificate at: http://www.sigma-aldrich.com

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).

Legal Information

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

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