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R8875

Rotenone

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

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Do Państwa/SKUDostępnośćCena netto
1 g
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801,00 zł
5 g
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1410,00 zł
10 g
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25 g
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3230,00 zł
2745,50 zł

Informacje o tej pozycji

Wzór empiryczny (zapis Hilla):
C23H22O6
Numer CAS:
Masa cząsteczkowa:
394.42
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
201-501-9
MDL number:
Beilstein/REAXYS Number:
6773081
Assay:
≥95%

801,00 zł


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Nazwa produktu

Rotenone, ≥95%

Quality Segment

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.
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Ta pozycja
45656557368CRM38703
Rotenone PESTANAL®, analytical standard

Supelco

45656

Rotenone

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.)


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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

Klasa składowania

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3



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Questions

1–5 of 5 Questions  
  1. 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
    1. This product is not soluble in aqueous solutions. Literature should be consulted for in vivo preparation methods.

      Helpful?

  2. For how long can the product maintain stability in powder form at 4 °C or -80 °C?

    1 answer
    1. 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.pdf

      Helpful?

  3. Can aliquots of rotenone resuspended in DMSO be stored at -20C?

    1 answer
    1. 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?

  4. What is the solubility in other compounds ?

    1 answer
    1. 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/mL

      Helpful?

  5. What's the solubility in DMSO

    1 answer
    1. 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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