FCCP

Product Name: FCCP
CAS No.: 370-86-5
Chemical Name: FCCP
Synonyms: FCCP;FCCCP;p-CF3O-CCP;Carbonyl Cyanide para Trifluoromethoxyphe;4-(TRIFLUOROMETHOXY)PHENYLAZOMALONONITRILE;CARBONOYLCYANID-4-TRIFLUORMETHOXYPHENYL-HYDRAZON;Trifluoromethoxy carbonylcyanide phenylhydrazone;MESOXALONITRILE 4-TRIFLUOROMETHOXYPHENYLHYDRAZONE;Carbonylcyanide-p-trifluoromethoxuphenylhydrazone;CARBONYL CYANIDE 4-TRIFLUOROMETHOXYPHENYLHYDRAZONE
CBNumber: CB0252618
Molecular Formula: C10H5F3N4O
Formula Weight: 254.17
MOL File: 370-86-5.mol

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FCCP Property

Melting point:: 174-175 °C (dec.)(lit.)
Boiling point:: 293.3±50.0 °C(Predicted)
Density: 1.34±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: acetone: 20 mg/mL, clear, very deep greenish yellow
form: powder
pka: 5.91±0.10(Predicted)
color: yellow
BRN: 664446
Stability:: Stable for 2 years from date of purchase as supplied. Protect from exposure to moisture. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
CAS DataBase Reference: 370-86-5

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Safety

Hazard Codes: T,Xi
Risk Statements: 25-43
Safety Statements: 36/37-45
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: FG5775000
Hazard Note: Irritant
HazardClass: 6.1(a)
PackingGroup: II
HS Code: 2928009090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H317May cause an allergic skin reaction

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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: C2920
Product name: Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone
Purity: ≥98% (TLC), powder
Packaging: 10mg
Price: $157
Updated: 2024/03/01

Sigma-Aldrich

Product number: C2920
Product name: Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone
Purity: ≥98% (TLC), powder
Packaging: 50mg
Price: $618
Updated: 2024/03/01

TCI Chemical

Product number: C3463
Product name: Carbonyl Cyanide 4-(Trifluoromethoxy)phenylhydrazone
Purity: >95.0%(GC)
Packaging: 10mg
Price: $125
Updated: 2024/03/01

TCI Chemical

Product number: C3463
Product name: Carbonyl Cyanide 4-(Trifluoromethoxy)phenylhydrazone
Purity: >95.0%(GC)
Packaging: 50mg
Price: $373
Updated: 2024/03/01

Cayman Chemical

Product number: 15218
Product name: FCCP
Purity: ≥98%
Packaging: 10mg
Price: $69
Updated: 2024/03/01

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FCCP Chemical Properties,Usage,Production

Description

FCCP (370-86-5) is an extremely potent uncoupler of mitochondrial oxidative phosphorylation (IC50 = 20 nM).1 Induces apoptosis in a variety of cell lines.2 Inhibits wild type and mutant beta-amyloid production in embryonic kidney 293 cells expressing either wild-type or “Swedish” mutant APP.3 An important tool for inhibiting mitochondrial membrane potential.2,4 Cell permeable.

Uses

FCCP is a potent uncoupler of oxidative phosphorylation in mitochondria that disrupts ATP synthesis by transporting protons across cell membranes. At 40 μM, FCCP induces complete depolymerization of microtubules by increasing intracellular pH via the disruption of the mitochondrial H+ gradient and by decreasing the stability of microtubules by impairing the binding of microtubule-associated proteins.[Cayman Chemical]

Definition

ChEBI: A hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group.

Biological Activity

A very potent uncoupler of oxidative phosphorylation in mitochondria.

Biochem/physiol Actions

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 a number of effects on cellular calcium. It also is 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.

in vitro

fccp increases the rate of cellular o2 consumption. in pc-3 and du-145 prostate cancer cells, the compound could significantly decrease hypoxic as well as normoxic hif-1 transcriptional activity which was in part mediated by down-regulation of the oxygen labile hif-1α and hif-2α protein levels. during hypoxic as well as normoxic, it decreases the expression of hif target genes, vegf and vegf receptor-2. [2]

in vivo

fccp reduces mitochondrial membrane potential and atp production in 8-cell mouse embryos. also, the number of inner cell mass cells decrease within blastocysts with unchanged blastocyst development. this perturbed embryonic mitochondrial function is concomitant with reduced birth weight in female offspring following embryo transfer, which persists until weaning. although fccp-treated males also exhibits reduced glucose tolerance as female, their insulin sensitivity and adiposity gain between 4 and 14 weeks is unchanged. reducing mitochondrial function and, thus, decreasing atp output in the precompacting embryo can influence offspring phenotype. [3]

storage

Store at RT

References

1) Benz R & McLaughlin S, (1983). The molecular mechanism of action of the proton ionophore FCCP (carbonylcyanide p-trifluoromethoxyphenylhydrazone).; Biophys J 41 381 2) Gautier et al. (2000), A moderate but not total decrease of mitochondrial membrane potential triggers apoptosis in neuron-like cells.; Neuroreport 11 2953 3) Connop et al. (1999), Novel effects of FCCP [carbonyl cyanide p-(trifluoromethoxy)phenylhydrazone] on amyloid precursor protein processing; J. Neurochem. 72 1457 4) Collins et al. (2000), Inositol 1,4,5-trisphosphate-induced Ca2+ release in inhibited by mitochondrial depolarization.; Biochem. J. 347 593

FCCP Preparation Products And Raw materials

Raw materials

Preparation Products

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FCCP Suppliers

Americas 1 Belgium 1 China 107 Europe 1 Germany 2 India 2 Japan 2 Switzerland 1 United Kingdom 9 United States 23 USA 1 Global 150

EMMX Biotechnology LLC

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Musechem

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TargetMol Chemicals Inc.

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InvivoChem

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Aladdin Scientific

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Combi-Blocks Inc.

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MP Biomedicals, Inc.

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View Lastest Price from FCCP manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: FCCP 370-86-5
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 20T
Release date: 2024-06-13

Career Henan Chemical Co

Product: carbonyl cyanide p-trifluoromethoxyphenylhydrazone 370-86-5
Price: US $8.80/KG
Min. Order: 1KG
Purity: 97%-99%
Supply Ability: 100kg
Release date: 2019-07-09

370-86-5, FCCPRelated Search:

Mirin COENZYME Q2 7-CHLORO-5-(2-CHLOROPHENYL)-1,5-DIHYDRO-4,1-BENZOTHIAZEPIN-2(3H)-ONE CITRININ BA, 3NH4 CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE DECYLUBIQUINONE Malononitrile FCCP 4-(Trifluoromethoxy)aniline 4-Methoxyphenylhydrazine hydrochloride 4-(TRIFLUOROMETHOXY)PHENYLHYDRAZINE HYDROCHLORIDE ACETONE PHENYLHYDRAZONE 4-(Difluoromethoxy)aniline (Trifluoromethoxy)benzene (DIFLUOROMETHOXY)BENZENE 1,1-DIFLUORODIMETHYL ETHER TRIFLUOROMETHYL METHYL ETHER

((4-(trifluoromethoxy)phenyl)hydrazono)-propanedinitril

MESOXALONITRILE 4-TRIFLUOROMETHOXYPHENYLHYDRAZONE

2-[2-[4-(TRIFLUOROMETHOXY)PHENYL]HYDRAZONO]MALONONITRILE

4-(TRIFLUOROMETHOXY)PHENYLAZOMALONONITRILE

mesoxalonitrile,(p-(trifluoromethoxy)phenyl)hydrazone

[[4-(trifluoromethoxy)phenyl]hydrazono]malononitrile

CARBONYL CYANIDE P-(TRIFLUOROMETHOXY)PHE NYLHYDRAZO

CARBONOYLCYANID-4-TRIFLUORMETHOXYPHENYL-HYDRAZON

FCCP, Mesoxalonitrile 4-trifluoromethoxyphenylhydrazone

2-[4-(Trifluoromethoxy)phenyl]hydrazonopropanedinitrile

p-CF3O-CCP

Carbonylcyanide-p-trifluoromethoxuphenylhydrazone

{2-[4-(Trifluoromethoxy)phenyl]hydrazinylidene}propane-1,3-dinitrile, 4-[2-(Dicyanomethylidene)hydrazino]-alpha,alpha,alpha-trifluoroanisole

Trifluoromethoxy carbonylcyanide phenylhydrazone

2-[2-[4-(Trifluoromethoxy)phenyl]hydrazinylidene]propanedinitrile

FCCCP

CARBONYL CYANIDE 4-TRIFLUOROMETHOXYPHENYLHYDRAZONE

CARBONYL CYANIDE P-(TRI-FLUOROMETHOXY)PHENYL-HYDRAZONE

CARBONYL CYANIDE P-TRIFLUOROMETHYL PHENYLHYDRAZONE

FCCP

Propanedinitrile, 2-[2-[4-(trifluoromethoxy)phenyl]hydrazinylidene]-

Propanedinitrile, [[4-(trifluoromethoxy)phenyl]hydrazono]-

2-[[4-(trifluoromethoxy)phenyl]hydrazinylidene]propanedinitrile

(4-(Trifluoromethoxy)phenyl)hydrazonopropanedinitrile

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazon

Carbonyl Cyanide para Trifluoromethoxyphe

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone|||Trifluoromethoxy carbonylcyanide phenylhydrazone

370-86-5

C10H5F3N4O

CF3OC6H4NHNCCN2

Enzyme Inhibitors

Enzymes, Inhibitors, and Substrates

Enzyme Inhibitors by Type

Organic Covalent Modifiers

Biochemicals and Reagents

BioChemical

Signalling

Caspases/Apoptosis