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C2920

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone

Name: Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone
Brand: SIGMA

≥98% (TLC), powder, Mitophagy inducer

Synonym(s):

FCCP, Mesoxalonitrile 4-trifluoromethoxyphenylhydrazone

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About This Item

Linear Formula:

CF₃OC₆H₄NHN=C(CN)₂

CAS Number:

370-86-5

Molecular Weight:

254.17

Beilstein:

664446

EC Number:

206-730-8

MDL number:

MFCD00009699

UNSPSC Code:

12352200

PubChem Substance ID:

24892549

NACRES:

NA.77

product name

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone, ≥98% (TLC), powder

Quality Level

300

Assay

≥98% (TLC)

form

powder

color

yellow

mp

174-175 °C (dec.) (lit.)

solubility

95% ethanol: soluble

storage temp.

2-8°C

SMILES string

FC(F)(F)Oc1ccc(N\N=C(/C#N)C#N)cc1

InChI

1S/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16H

InChI key

BMZRVOVNUMQTIN-UHFFFAOYSA-N

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General description

FCCP is a protonophore (H+ ionophore) and uncoupler of oxidative phosphorylation in mitochondria. It is capable of depolarizing plasma and mitochondrial membranes. FCCP has been shown to have several effects on cellular calcium. It is also reported to inhibit a background K⁺ current and induce a small inward current, reduce pH by 0.1 unit, and induce a rise of intracellular [Na⁺]. FCCP stimulates Mg²⁺-ATPase activity, inhibits β-amyloid production, and mimics the effect of selective glutamate agonist N-methyl-D-aspartate (NMDA) on mitochondrial superoxide production.

Application

Carbonylcyanide 4-(trifluoromethoxy)phenylhydrazone (FCCP) has been used as an uncouplerin cell culture: to study its effects on murine thermogenic adipocytes, tostudy its effects on β-oxidation in mouse mitochondria, to study its effects on the metabolism in bone marrow-derived dendriticcells from mouse

Pictograms

GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314,H317,H413

Precautionary Statements

P260 - P273 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 4 - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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FCCP depolarizes plasma membrane potential by activating proton and Na+ currents in bovine aortic endothelial cells.

Kyu-Sang Park et al.

Pflugers Archiv : European journal of physiology, 443(3), 344-352 (2002-01-26)

We investigated the effects of carbonylcyanide p-trifluoromethoxyphenylhydrazone (FCCP), a protonophore and uncoupler of mitochondrial oxidative phosphorylation in mitochondria, on plasma membrane potential and ionic currents in bovine aortic endothelial cells (BAECs). The membrane potential and ionic currents of BAECs were

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The Parkinson's disease (PD)-related ubiquitin ligase Parkin and mitochondrial kinase PINK1 function together in the clearance of damaged mitochondria. Upon mitochondrial depolarization, Parkin translocates to mitochondria in a PINK1-dependent manner to ubiquitinate outer mitochondrial membrane proteins. According to the current

Optimization of experimental conditions and measurement of oxygen consumption rate (OCR) in zebrafish embryos exposed to organophosphate flame retardants (OPFRs).

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