Merck
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C2759

Sigma-Aldrich

Carbonyl cyanide 3-chlorophenylhydrazone

≥97% (TLC), powder

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

Quality Level

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
C2920P1645B6936
assay

≥97% (TLC)

assay

≥98% (TLC)

assay

≥98% (TLC)

assay

≥98% (HPLC)

form

powder

form

powder

form

powder

form

solid

color

yellow to orange

color

yellow

color

white

color

light yellow

solubility

DMSO: 100 mM

solubility

95% ethanol: soluble

solubility

H2O: 25 mg/mL (with heat or sonication)

solubility

DMSO: >14 mg/mL

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

100

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

Signal Word

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 Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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