Skip to Content
Merck

R8875

Rotenone

≥95% (HPLC), powder, NADH-CoQ reductase inhibitor

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C23H22O6
CAS Number:
Molecular Weight:
394.42
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
201-501-9
MDL number:
Beilstein/REAXYS Number:
6773081
Assay:
≥95%
Quality level:
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist


Product Name

Rotenone, ≥95%

Quality Level

assay

≥95%

bp

210-220 °C/0.5 mmHg (lit.)

mp

159-164 °C (lit.)

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 belongs to the retinoid family. It is naturally present in Leguminosa plants and is considered to be cytotoxic. It is commonly used as an insecticide and a pesticide.

Application

Rotenone has been used:
  • to study its effect on cell proliferation
  • to detect the production of cellular reactive oxygen species in isolated rat forebrain mitochondria
  • to measure mitochondrial enzymatic activity

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).

Preparation Note

This product is soluble in DMSO at 0.5 mg/ml. Other sources suggest it can be dissolved in DMSO up to 100 mM, however this has not been verified.


Still not finding the right product?

Explore all of our products under Rotenone


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

wgk

WGK 3


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

R8875-5G:4.548173209579E12 + R8875-10G:4.548173209548E12 + R8875-1G:4.548173209555E12 + R8875-25G:4.548173209562E12

jan



Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library



Ca2+-induced oxidative stress in brain mitochondria treated with the respiratory chain inhibitor rotenone
Sousa SC, et al.
Febs Letters, 543(1-3), 179-183 (2003)
Parkinson's Disease and Movement Disorders, 81-81 (2007)
Metformin decreases glucose oxidation and increases the dependency of prostate cancer cells on reductive glutamine metabolism
Fendt SM, et al.
Cancer Research (2013)