C2759

Carbonyl Cyanide m-Chlorophenylhydrazone

≥97% (TLC), powder, mitophagy inducer

• Synonym(s): m-Cl-CCP, CCCP, Mesoxalonitrile 3-chlorophenylhydrazone
• Empirical Formula (Hill Notation): C₉H₅ClN₄
• CAS Number: 555-60-2
• Molecular Weight: 204.62
• Beilstein/REAXYS Number: 1842102
• EC Number: 209-103-7
• MDL number: MFCD00001848
• UNSPSC Code: 12352200
• PubChem Substance ID: 24892523
• NACRES: NA.77

Properties

• product name: Carbonyl cyanide 3-chlorophenylhydrazone, ≥97% (TLC), powder
• Quality Level: 200
• 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

Description

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.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301 + H311 + H331,H315,H319,H335
• pcodes: P261 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311 - P305 + P351 + P338
• 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