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CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE

Product Name
CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE
CAS No.
555-60-2
Chemical Name
CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE
Synonyms
CCCP;Carbonyl Cyanide;(3-CHLOROPHENYL)HYDRAZONOMALONONITRILE;MESOXALONITRILE 3-CHLOROPHENYLHYDRAZONE;CCCP;CCCPH;M-CL-CCP;m-Cl-CCP (CCCP);BUTTPARK 91\04-41;TIMTEC-BB SBB003506;CCCP apoptosis inducer;3-chlorophenylhydrazone
CBNumber
CB0421559
Molecular Formula
C9H5ClN4
Formula Weight
204.62
MOL File
555-60-2.mol
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CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE Property

Melting point:
170-175 °C (dec.)
Boiling point:
333.84°C (rough estimate)
Density 
1.3807 (rough estimate)
refractive index 
1.6110 (estimate)
storage temp. 
-20°C
solubility 
methanol: 10 mg/mL, clear, very deep yellow
form 
powder
pka
6.00±0.10(Predicted)
color 
yellow to orange
Water Solubility 
Insoluble in water. Soluble in DMSO (5 mg/ml), ethanol (1 mg/ml) and methanol (10 mg/ml).
BRN 
1842102
Exposure limits
NIOSH: IDLH 25 mg/m3
InChIKey
UGTJLJZQQFGTJD-UHFFFAOYSA-N
CAS DataBase Reference
555-60-2(CAS DataBase Reference)
EPA Substance Registry System
Propanedinitrile, [(3-chlorophenyl)hydrazono]- (555-60-2)
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Safety

Hazard Codes 
T
Risk Statements 
23/24/25-36/37/38
Safety Statements 
26-36/37-45
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
FG5600000
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
III
HS Code 
29280090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C2759
Product name
Carbonyl cyanide 3-chlorophenylhydrazone
Purity
≥97% (TLC), powder
Packaging
1g
Price
$176
Updated
2024/03/01
Sigma-Aldrich
Product number
215911
Product name
Carbonyl Cyanide
Packaging
250mg
Price
$130
Updated
2024/03/01
Alfa Aesar
Product number
L06932
Product name
Carbonyl cyanide 3-chlorophenylhydrazone, 98%
Packaging
100mg
Price
$25.4
Updated
2024/03/01
Alfa Aesar
Product number
L06932
Product name
Carbonyl cyanide 3-chlorophenylhydrazone, 98%
Packaging
500mg
Price
$67.3
Updated
2024/03/01
Cayman Chemical
Product number
25458
Product name
CCCP
Purity
≥98%
Packaging
100mg
Price
$32
Updated
2024/03/01
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CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE Chemical Properties,Usage,Production

Description

CCCP is a protonophore mitochondrial uncoupler that increases membrane permeability to protons, leading to a disruption in the mitochondrial membrane potential. It inhibits mitochondrial respiration and ATPase activity when used at concentrations of 110 and 35 nM, respectively. CCCP inhibits activation of stimulation of interferon genes (STING), decreasing the expression of downstream STING targets, including IFN-β, TBK1, and IRF3 when used at a concentration of 50 μM in RAW 264.7 cells. It induces mitochondrial fission in a manner dependent on the GTPase Drp1. CCCP (4 mg/kg) increases body temperature as well as left ventricular systolic and diastolic dimensions and decreases fractional shortening in rats. It also increases myocardial glucose and fatty acid uptake in rats.

Chemical Properties

yellow to orange-brown crystalline powder

Uses

Carbonyl cyanide 3-chlorophenylhydrazone is a widely used uncoupler of oxidative phosphorylation.

Uses

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

Definition

ChEBI: CCCP is a member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death. It has a role as a geroprotector, an antibacterial agent and an ionophore. It is a nitrile, a hydrazone and a member of monochlorobenzenes. It is functionally related to a hydrazonomalononitrile.

Biological Activity

Widely used uncoupler of oxidative phosphorylation.

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.

in vitro

a genetic β-galactoside reporter system with a disk diffusion assay on macconkey lactose agar petri plates to monitor maintenance of the bacteriophage λ prophage state and viral induction in escherichia coli k-12. it presented evidence that the phage λ major lytic promoters, pl and pr, are activated via cells containing the reporters following exposure to the energy poison cccp. requirement of expression of the λ lytic promoters in response to cccp is host reca function and an auto-cleavable ci repressor, as does sos induction of the λ prophage occurring by a dna damage-dependent pathway. cccp-mediated activation of the λ lytic promoters required λ cro function. cccp does not modulate an sfi-lacz sos reporter [1]. the uncoupler cccp blocks oxidative phosphorylation by damaging the proton gradient. an anion cccp can bind a proton. but cccp with a delocalized negative charge allows it to cross the lipid bilayer in the unprotonated form, while weak acids cross the hydrophobic membrane only when protonated. many protons can be transported by one molecule of cccp across the inner membrane. it is described that a genetic reporter system to monitor maintenance of the λ prophage state and viral induction, and evidence is presented that it activates the major leftward and rightward lytic promoters of the λ prophage that cells are exposed to the energy poison cccp.

storage

Store at RT

References

[1]. thomason lc, court dl. evidence that bacteriophage λ lysogens may induce in response to the proton motive force uncoupler cccp. fems microbiol lett. 2016 feb;363(3).

CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE Preparation Products And Raw materials

Raw materials

Preparation Products

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CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE Suppliers

TOKYO CHEMICAL INDUSTRY CO., LTD.
Tel
03-36680489
Fax
03-3668-0520
Email
Sales-JP@TCIchemicals.com
Country
Japan
ProdList
28387
Advantage
80
Nacalai Tesque, Inc.
Tel
--
Fax
--
Email
info-tech@nacalai.co.jp
Country
Japan
ProdList
6046
Advantage
75
Wako Pure Chemical Industries, Ltd.
Tel
--
Fax
--
Email
labchem-tec@wako-chem.co.jp
Country
Japan
ProdList
6819
Advantage
80
Kanto Chemical Co., Inc.
Tel
--
Fax
--
Email
reag-info@gms.kanto.co.jp
Country
Japan
ProdList
6756
Advantage
74
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View Lastest Price from CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE 555-60-2
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-08-11
Career Henan Chemical Co
Product
CCCP 555-60-2
Price
US $1.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
200kg
Release date
2018-12-25

555-60-2, CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONERelated Search:


  • (3-CHLOROPHENYL)HYDRAZONOMALONONITRILE;MESOXALONITRILE 3-CHLOROPHENYLHYDRAZONE;CCCP
  • [(3-chlorophenyl)hydrazono]-propanedinitril
  • m-chlorophenylcarbonylcyanidehydrazone
  • mesoxalonitrile,(m-chlorophenyl)hydrazone
  • M-CL-CCP
  • MESOXALONITRILE (3-CHLOROPHENYL)HYDRAZONE
  • BUTTPARK 91\04-41
  • CARBONYL CYANIDE M-CHLOROPHENYL-HYDRAZONE
  • CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE
  • CCCP
  • 3-chlorophenylhydrazone
  • [(3-CHLOROPHENYL)HYDRAZONO]PROPANEDINITRILE
  • [(3-chlorophenyl)hydrazono]malononitrile
  • CARBONYL CYANIDE M-CHLOROPHENYL &
  • Carbonylcyanide3-chlorophenylhydrazone,98%
  • Carbonyl cyanide 3-chlorophenylhydrazone, 99+%
  • Carbonylcyanid-m-chlorphenylhydrazon
  • m-Cl-CCP, Carbonyl cyanide 3-chlorophenylhydrazone, CCCP, Mesoxalonitrile (3-chlorophenyl)hydrazone, Mesoxalonitrile 3-chlorophenylhydrazone
  • m-Cl-CCP, CCCP, Mesoxalonitrile 3-chlorophenylhydrazone
  • Carbonyl cyanide m-chlorophenylhydrazone, 99+%
  • 2-[(3-Chlorophenyl)hydrazono]propanedinitrile
  • CCCPH
  • Carbonyl cyanide 3-chlorophenylhydrazone,m-Cl-CCP, CCCP, Mesoxalonitrile 3-chlorophenylhydrazone
  • (3-chlorophenyl)carbonohydrazonoyl dicyanide
  • Carbonyl Cyanide
  • TIMTEC-BB SBB003506
  • ((3-chlorophenyl)hydrazono)-propanedinitril
  • Carbonyl Cyanide m-Chlorophenylhydrazone - CAS 555-60-2 - Calbiochem
  • Propanedinitrile, 2-[2-(3-chlorophenyl)hydrazinylidene]-
  • 2-[2-(3-Chlorophenyl)hydrazinylidene]propanedinitrile
  • CCCP apoptosis inducer
  • m-Cl-CCP (CCCP)
  • 2-[(3-chlorophenyl)hydrazinylidene]propanedinitrile
  • N-(3-chlorophenyl)carbonohydrazonoyldicyanide
  • CCCP,Mesoxalonitrile 3-chlorophenylhydrazone
  • 555-60-2
  • C9H5ClN4
  • C9H5CIN4
  • ClC6H4NHNCCN2
  • Organic Covalent Modifiers
  • Enzyme Inhibitors
  • Enzymes, Inhibitors, and Substrates
  • Enzyme Inhibitors by Type
  • BioChemical
  • Biochemicals and Reagents
  • Caspases/Apoptosis