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
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
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.
N-Bromosuccinimide Price
- Product number
- C2920
- Product name
- Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone
- Purity
- ≥98% (TLC), powder
- Packaging
- 10mg
- Price
- $157
- Updated
- 2024/03/01
- Product number
- C2920
- Product name
- Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone
- Purity
- ≥98% (TLC), powder
- Packaging
- 50mg
- Price
- $618
- Updated
- 2024/03/01
- Product number
- C3463
- Product name
- Carbonyl Cyanide 4-(Trifluoromethoxy)phenylhydrazone
- Purity
- >95.0%(GC)
- Packaging
- 10mg
- Price
- $125
- Updated
- 2024/03/01
- Product number
- C3463
- Product name
- Carbonyl Cyanide 4-(Trifluoromethoxy)phenylhydrazone
- Purity
- >95.0%(GC)
- Packaging
- 50mg
- Price
- $373
- Updated
- 2024/03/01
- Product number
- 15218
- Product name
- FCCP
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $69
- Updated
- 2024/03/01
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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View Lastest Price from FCCP manufacturers
- 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