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Merck

45656

Rotenone

PESTANAL®, analytical standard

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About This Item

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

Key Documents

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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

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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

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 and biological samples 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).

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

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

45656-1EA:4548173267111 + 45656-250MG:4548173900100 + 45656-BULK: + 45656-VAR:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG5865
BCCB4131
BCBV6839
BCBT2258
BCBS4281V

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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)
Jun Matsumoto et al.
Antimicrobial agents and chemotherapy, 52(1), 164-170 (2007-10-24)
Alveolar echinococcosis, which is due to the massive growth of larval Echinococcus multilocularis, is a life-threatening parasitic zoonosis distributed widely across the northern hemisphere. Commercially available chemotherapeutic compounds have parasitostatic but not parasitocidal effects. Parasitic organisms use various energy metabolic
M Tasselli et al.
Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society, 25(3), e183-e193 (2013-01-04)
The systemic rotenone model of Parkinson's disease (PD) accurately replicates many aspects of the pathology of human PD, especially neurodegeneration of the substantia nigra and lesions in the enteric nervous system (ENS). Nevertheless, the precise effects of oral rotenone on
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