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Merck
CN

45656

Rotenone

PESTANAL®, analytical standard

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About This Item

Empirical Formula (Hill Notation):
C23H22O6
CAS Number:
Molecular Weight:
394.42
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
EC Number:
201-501-9
Beilstein/REAXYS Number:
6773081
MDL number:
Technical Service
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grade

analytical standard

Quality Level

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

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).

Legal Information

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


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pictograms

Skull and crossbonesEnvironment

signalword

Danger

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

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

农药列管产品

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Determination of rotenone residues in raw honey by solid-phase extraction and high-performance liquid chromatography
Jimenez.JJ, et al.
Journal of Chromatography A, 871(1-2), 67-73 (2000)
Determination of rotenone in river water utilizing packed capillary column switching liquid chromatography with UV and time-of-flight mass spectrometric detection
Holm A, et al.
Journal of Chromatography A, 983(1-2), 43-50 (2003)
Botanical Pesticides in Agriculture, 983(1-2), 43-50 (1996)



Global Trade Item Number

SKUGTIN
45656-250MG04061832341545