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C2759

Sigma-Aldrich

Carbonyl cyanide 3-chlorophenylhydrazone

≥97% (TLC), powder

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Synonym(s):
m-Cl-CCP, CCCP, Mesoxalonitrile 3-chlorophenylhydrazone
Empirical Formula (Hill Notation):
C9H5ClN4
CAS Number:
Molecular Weight:
204.62
Beilstein/REAXYS Number:
1842102
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

≥97% (TLC)

form

powder

color

yellow to orange

solubility

DMSO: 100 mM

storage temp.

−20°C

SMILES string

Clc1cccc(N\N=C(\C#N)C#N)c1

InChI

1S/C9H5ClN4/c10-7-2-1-3-8(4-7)13-14-9(5-11)6-12/h1-4,13H

InChI key

UGTJLJZQQFGTJD-UHFFFAOYSA-N

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This Item
C2920C0985P7561
vibrant-m

P7561

Phentolamine methanesulfonate salt

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

200

assay

≥97% (TLC)

assay

≥98% (TLC)

assay

≥98% (HPLC)

assay

≥98% (TLC)

color

yellow to orange

color

yellow

color

-

color

white to off-white

solubility

DMSO: 100 mM

solubility

95% ethanol: soluble

solubility

-

solubility

ethanol: 26 mg/mL, H2O: 50 mg/mL

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

-

Application

Carbonyl cyanide 3-chlorophenylhydrazone (CCCP) has been used:
  • in the inhibition of efflux pump in clinical Pseudomonas aeruginosa
  • to inhibit oxidative phosphorylation activity of mitochondria in human Beas-2B bronchial epithelial cells
  • to prepare carbonyl cyanide m-chlorophenylhydrazone solution for oxidative and mitochondrial stress assay and mitophagy induction in Caenorhabditis elegans

Biochem/physiol Actions

Carbonyl cyanide 3-chlorophenylhydrazone (CCCP) induces mitophagy in mammalian cells. CCCP suppresses the expression of few electron transport chain (ETC) proteins. Protonophore (H+ ionophore) and uncoupler of oxidative phosphorylation in mitochondria. Shown to have a number of effects on cellular calcium. Inhibits secretion of hepatic lipase and partially inhibits the pH gradient-activated Cl- uptake and Cl-/Cl- exchange activities in brush-border membrane vesicles.

pictograms

Skull and crossbones

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

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


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