This product is not soluble in aqueous solutions. Literature should be consulted for in vivo preparation methods.
R8875
Rotenone
≥95% (HPLC), powder, NADH-CoQ reductase inhibitor
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1 G
PLN 801.00
5 G
PLN 1,410.00
10 G
PLN 2,130.00
25 G
PLN 3,000.50
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
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Product Name
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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Related Categories
1 of 4
This Item | 45656 | 557368 | CRM38703 |
|---|---|---|---|
| assay ≥95% | assay - | assay ≥98% (HPLC) | assay - |
| Quality Level 200 | Quality Level 100 | Quality Level 100 | Quality Level 300 |
| bp 210-220 °C/0.5 mmHg (lit.) | bp 210-220 °C/0.5 mmHg (lit.) | bp - | bp 210-220 °C/0.5 mmHg (lit.) |
| mp 159-164 °C (lit.) | mp 159-164 °C (lit.) | mp - | mp 159-164 °C (lit.) |
Application
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.[5]
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
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
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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)
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)
Related Content
Product Information Sheet
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I dissolved this new product in 10 mL pure DMSO for 1 mM stock, as per protocol. But when diluted with DMEM/F12 or PBS for cell treatment, it forms white precipitate. How to fix this? Urgent help needed!!
1 answer-
Helpful?
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For how long can the product maintain stability in powder form at 4 °C or -80 °C?
1 answer-
The recommended storage temperature for this material is ambient or room temperature. Studies have not been conducted to evaluate the stability or shelf life impact of the product when stored at other temperatures. In the original sealed container, the compound is quite stable at room temperature. Please see the link below to review additional information available in the product datasheet:
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/366/380/r8875pis.pdfHelpful?
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Can aliquots of rotenone resuspended in DMSO be stored at -20C?
1 answer-
The solution stability has not been determined. However, a similar product, 557368, notes that "following reconstitution, aliquot, flush with nitrogen, and store at -70°C. Stock solutions are stable for up to 1 month at -70°C".
Helpful?
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What is the solubility in other compounds ?
1 answer-
This product is tested for solubility at 50 mg/mL in chloroform. Rotenone is poorly soluble in water at approximately 0.25-0.50 uM. Other options include Ethanol and DMSO.
Ethanol: 5 mg/mL (higher concentrations may be achieved with heat and sonication)
DMSO: 50 mg/mLHelpful?
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What's the solubility in DMSO
1 answer-
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.
Helpful?
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