R8875
Rotenone
≥95% (HPLC), powder, NADH-CoQ reductase inhibitor
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크기 선택
제품정보 (DICE 배송 시 비용 별도)
실험식(Hill 표기법):
C23H22O6
CAS 번호:
Molecular Weight:
394.42
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
201-501-9
MDL number:
Beilstein/REAXYS Number:
6773081
제품 이름
Rotenone, ≥95%
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
SMILES string
COc1cc2OCC3Oc4c5C[C@@H](Oc5ccc4C(=O)C3c2cc1OC)C(C)=C
assay
≥95%
bp
210-220 °C/0.5 mmHg (lit.)
mp
159-164 °C (lit.)
Quality Level
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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).
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.
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.
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
저장 등급
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
Metformin decreases glucose oxidation and increases the dependency of prostate cancer cells on reductive glutamine metabolism
Fendt SM, et al.
Cancer Research (2013)
Loss of Sirt1 promotes prostatic intraepithelial neoplasia, reduces mitophagy, and delays PARK2 translocation to mitochondria
Di SG, et al.
The American Journal of Pathology, 185(1), 266-279 (2015)
Jin Bu et al.
Life sciences, 231, 116581-116581 (2019-06-21)
The aims of this study were to investigate the effect of colonic electrical stimulation (CES) on delayed colonic transit in Parkinson's disease (PD) model induced by rotenone and its possible mechanisms. Sprague-Dawley male rats were implanted with a pair of
Parkinson's Disease and Movement Disorders, 81-81 (2007)
Overexpression of TFAM or twinkle increases mtDNA copy number and facilitates cardioprotection associated with limited mitochondrial oxidative stress
Ikeda M, et al.
PLoS ONE, 10(3), e0119687-e0119687 (2015)
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Product Information Sheet
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