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Sigma-Aldrich Rotenone. ≥95% (HPLC), powder, NADH-CoQ reductase inhibitor. 5 g
List Price $437.32 Your Price $437.32
Sigma-Aldrich Rotenone. ≥95% (HPLC), powder, NADH-CoQ reductase inhibitor. 5 g - SIAL (Additional S&H Or Hazmat Fees May Apply)
NETA PART: SIAL-R8875-5G
MFG.PART: R8875-5G
UNSPSC: 12352200
Manufacturer: Sigma-Aldrich


Product Name
Rotenone, ≥95%
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
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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.[1]
Application
Rotenone has been used:
- to study its effect on cell proliferation[2]
- to detect the production of cellular reactive oxygen species[3] in isolated rat forebrain mitochondria[4]
- to measure mitochondrial enzymatic activity[5]
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.
Other Notes
2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research
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_germany
WGK 3
| SKU | SIAL-R8875-5G |
|---|---|
| Supplier Part Number | R8875-5G |
| UM | EA |
| UNSPSC | 12352200 |
| Manufacturer | Sigma-Aldrich |
| ProductLine | SIAL |
| Qty | 1 |
| MinOrderQty | 1 |
| Weight | 10.000000 |
| Lead Time | 9 |
| CAS Number | 83-79-4 |
| Energy Star | No |
| Green | No |
| Controlled | N |

