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C2920

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone

≥98% (HPLC), 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/REAXYS Number:
664446
EC Number:
206-730-8
MDL number:
MFCD00009699
UNSPSC Code:
12352200
PubChem Substance ID:
24892549
NACRES:
NA.77

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Product Name

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

Quality Level

300

assay

≥98% (HPLC)

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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1 of 4

This Item
C2759C2020SML2959
Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone ≥98% (HPLC), powder

Sigma-Aldrich

C2920

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone

Carbonyl cyanide 3-chlorophenylhydrazone ≥97% (TLC), powder

Sigma-Aldrich

C2759

Carbonyl cyanide 3-chlorophenylhydrazone

α-Cyano-4-hydroxycinnamic acid ≥98% (TLC), powder

Sigma-Aldrich

C2020

α-Cyano-4-hydroxycinnamic acid

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone Ready Made Solution ≥98% (HPLC), 2.54 mg/mL (10mM) in DMSO

Sigma-Aldrich

SML2959

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone Ready Made Solution

assay

≥98% (TLC)

assay

≥97% (TLC)

assay

≥98% (TLC)

assay

≥98% (HPLC)

form

powder

form

powder

form

powder

form

liquid

Quality Level

300

Quality Level

200

Quality Level

300

Quality Level

100

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

solubility

95% ethanol: soluble

solubility

DMSO: 100 mM

solubility

H2O: slightly soluble, methanol: water: soluble, polar organic solvents: soluble

solubility

-

color

yellow

color

yellow to orange

color

yellow

color

-

General description

FCCP is a protonophore (H+ ionophore) and uncoupler of oxidative phosphorylation in mitochondria.[1] 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[2], tostudy its effects on β-oxidation in mouse mitochondria[3], to study its effects on the metabolism in bone marrow-derived dendriticcells from mouse[4]

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000436114
0000436114
0000409669
0000409669
0000374029

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Aleksandar Rakovic et al.
Cell death and differentiation, 26(8), 1428-1441 (2018-10-31)
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
Lisa Kappler et al.
American journal of physiology. Endocrinology and metabolism, 317(2), E374-E387 (2019-06-19)
Mitochondria are dynamic organelles with diverse functions in tissues such as liver and skeletal muscle. To unravel the mitochondrial contribution to tissue-specific physiology, we performed a systematic comparison of the mitochondrial proteome and lipidome of mice and assessed the consequences
Isa Mambetsariev et al.
Journal of clinical medicine, 8(7) (2019-07-19)
Small cell lung cancer (SCLC) is an aggressive neuroendocrine disease with an overall 5 year survival rate of ~7%. Although patients tend to respond initially to therapy, therapy-resistant disease inevitably emerges. Unfortunately, there are no validated biomarkers for early-stage SCLC
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
Federica Morani et al.
Scientific reports, 9(1), 11878-11878 (2019-08-17)
Autosomal recessive spastic ataxia of Charlevoix-Saguenay (ARSACS) is a rare early-onset neurological disease caused by mutations in SACS, which encodes sacsin. The complex architecture of sacsin suggests that it could be a key player in cellular protein quality control system.
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