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557368

Rotenone

≥98% (HPLC), solid, NADH-CoQ reductase inhibitor, Calbiochem

Synonym(s):

Rotenone

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About This Item

Empirical Formula (Hill Notation):
C23H22O6
CAS Number:
83-79-4
Molecular Weight:
394.42
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD09025614
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze, protect from light
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Product Name

Rotenone, A mitochondrial toxin and a potent, reversible, and competitive inhibitor of complex I (NADH-CoQ reductase) of the respiratory chain.

Quality Level

100

description

Merck USA index - 14 8271

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

white to off-white

solubility

ethanol: 5 mg/mL, DMSO: 50 mg/mL, chloroform: 50 mg/mL

shipped in

ambient

storage temp.

10-30°C

SMILES string

O1[C@H]2[C@H](c5c(cc(c(c5)OC)OC)OC2)C(=O)c3c1c4c(cc3)O[C@H](C4)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

A mitochondrial toxin and a potent, reversible, and competitive inhibitor of complex I (NADH-CoQ reductase) of the respiratory chain. Also inhibits cellular proliferation in mouse liver.

Biochem/physiol Actions

Cell permeable: no
Primary Target
NADH-CoQ reductase
Product does not compete with ATP.
Reversible: yes

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot, flush with nitrogen, and store at -70°C. Stock solutions are stable for up to 1 month at -70°C.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
Kopustinskiene, D.M., et al. 2001. Eur. J. Pharmacol.428, 311.
Higgins, D.S., Jr. and Greenamyre, J.T. 1996. J. Neurosci. 16, 3807.
Cunningham, M.L., et al. 1995. Cancer Lett. 95, 93.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Toxic (F)

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pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

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

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

557368-1GM: + 557368-MG:

jan

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Aastha Garde et al.
STAR protocols, 3(2), 101429-101429 (2022-06-07)
Measuring ATP levels within the cytosol of living cells in animals is important to understand how cellular activities are energetically supported, but is challenging because of tissue complexity and ATP sensor limitations. In this protocol, we describe how to quantify
Andaleb Kholmukhamedov et al.
The Journal of biological chemistry, 298(9), 102336-102336 (2022-08-06)
Mitochondrial chelatable iron contributes to the severity of several injury processes, including ischemia/reperfusion, oxidative stress, and drug toxicity. However, methods to measure this species in living cells are lacking. To measure mitochondrial chelatable iron in living cells, here we synthesized
Localized glucose import, glycolytic processing, and mitochondria generate a focused ATP burst to power basement-membrane invasion.
Garde, et al.
Developmental Cell, 57, 732-749 (2023)
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Global Trade Item Number

SKUGTIN
557368-1GMCN04055977268034