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C2920

Sigma-Aldrich

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone

≥98% (TLC), powder

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Synonym(s):
FCCP, Mesoxalonitrile 4-trifluoromethoxyphenylhydrazone
Linear Formula:
CF3OC6H4NHN=C(CN)2
CAS Number:
Molecular Weight:
254.17
Beilstein/REAXYS Number:
664446
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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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1 of 4

This Item
C2759C2020N7634
α-Cyano-4-hydroxycinnamic acid ≥98% (TLC), powder

C2020

α-Cyano-4-hydroxycinnamic acid

Nifedipine ≥98% (HPLC), powder

N7634

Nifedipine

assay

≥98% (TLC)

assay

≥97% (TLC)

assay

≥98% (TLC)

assay

≥98% (HPLC)

Quality Level

300

Quality Level

-

Quality Level

-

Quality Level

200

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

95% ethanol: soluble

solubility

DMSO: 100 mM

solubility

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

solubility

DMSO: soluble, ethanol: soluble

color

yellow

color

yellow to orange

color

yellow

color

yellow

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

CorrosionExclamation mark

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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