FCCP
- CAS No.
- 370-86-5
- Chemical Name:
- FCCP
- Synonyms
- FCCP;FCCCP;p-CF3O-CCP;FCCP, 10 mM in DMSO;Carbonyl Cyanide para Trifluoromethoxyphe;4-(TRIFLUOROMETHOXY)PHENYLAZOMALONONITRILE;CARBONOYLCYANID-4-TRIFLUORMETHOXYPHENYL-HYDRAZON;Trifluoromethoxy carbonylcyanide phenylhydrazone;MESOXALONITRILE 4-TRIFLUOROMETHOXYPHENYLHYDRAZONE;Carbonylcyanide-p-trifluoromethoxuphenylhydrazone
- CBNumber:
- CB0252618
- Molecular Formula:
- C10H5F3N4O
- Molecular Weight:
- 254.17
- MDL Number:
- MFCD00009699
- MOL File:
- 370-86-5.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
| Appearance | bright yellow crystals |
| 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. |
| InChI | 1S/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16H |
| InChIKey | BMZRVOVNUMQTIN-UHFFFAOYSA-N |
| SMILES | FC(F)(F)Oc1ccc(N\N=C(/C#N)C#N)cc1 |
| CAS DataBase Reference | 370-86-5 |
| FDA UNII | SQR3W2FLV5 |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS05,GHS07 |
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|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H314-H317-H413 | |||||||||
| Precautionary statements | P260-P273-P280-P301+P312-P303+P361+P353-P305+P351+P338 | |||||||||
| PPE | Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges | |||||||||
| 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 | |||||||||
| Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials |
|||||||||
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Chronic 4 Eye Dam. 1 Skin Corr. 1B Skin Sens. 1 |
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| NFPA 704 |
|
FCCP price More Price(76)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | C2920 | Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone ≥98% (TLC), powder | 370-86-5 | 10mg | $173 | 2026-04-30 | Buy |
| Sigma-Aldrich | C2920 | Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone ≥98% (TLC), powder | 370-86-5 | 50mg | $681 | 2026-04-30 | Buy |
| TCI Chemical | C3463 | Carbonyl Cyanide 4-(Trifluoromethoxy)phenylhydrazone >95.0%(GC) | 370-86-5 | 10mg | $125 | 2026-04-30 | Buy |
| TCI Chemical | C3463 | Carbonyl Cyanide 4-(Trifluoromethoxy)phenylhydrazone >95.0%(GC) | 370-86-5 | 50mg | $373 | 2026-04-30 | Buy |
| Cayman Chemical | 15218 | FCCP ≥98% | 370-86-5 | 10mg | $80 | 2026-04-30 | Buy |
FCCP Chemical Properties, Uses, 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] R BENZ S M. The molecular mechanism of action of the proton ionophore FCCP (carbonylcyanide p-trifluoromethoxyphenylhydrazone).[J]. Biophysical journal, 1983, 41 3: 381-398. DOI:10.1016/s0006-3495(83)84449-x
[2] I GAUTIER. A moderate but not total decrease of mitochondrial membrane potential triggers apoptosis in neuron-like cells.[J]. Neuroreport, 2000, 11 13: 2953-2956. DOI:10.1097/00001756-200009110-00024
[3] BRUCE P. CONNOP. Novel Effects of FCCP [Carbonyl Cyanide p-(Trifluoromethoxy)phenylhydrazone] on Amyloid Precursor Protein Processing[J]. Journal of Neurochemistry, 2001, 72 4: 1457-1465. DOI:10.1046/j.1471-4159.1999.721457.x
[4] T J COLLINS. Inositol 1,4,5-trisphosphate-induced Ca2+ release is inhibited by mitochondrial depolarization.[J]. Biochemical Journal, 2000, 347 Pt 2: 593-600. DOI:10.1042/0264-6021:3470593
FCCP Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| amyjet | 4006800868;027-59626688 18771149750 | sales@amyjet.com | China | 2909 | 58 |
| Nodado Polysaccharide (Dalian) Pharmaceutical Technology Co., Ltd | 13840935583 13840935583 | nuodaduotang@163.com | China | 52 | 58 |
| Shanghai Boyle Chemical Co., Ltd. | sales@boylechem.com | China | 2915 | 55 | |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| TCI (Shanghai) Development Co., Ltd. | 021-67121386 | Sales-CN@TCIchemicals.com | China | 24512 | 81 |
| Beijing HwrkChemical Technology Co., Ltd | 89508211 18501085097 | sales.bj@hwrkchemical.com | China | 9407 | 55 |
| Ascent Scientific | 4401179829988 | customerservice@ascentscientific.co.uk | United Kingdom | 279 | 60 |
| Nanjing Chemlin Chemical Co., Ltd | 025-83697070 13770331960 | info@chemlin.com.cn | China | 16305 | 64 |
| Dalian Meilun Biotech Co., Ltd. | 0411-62910999 13889544652 | sales@meilune.com | China | 4765 | 58 |
View Latest Price from FCCP manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-08-08 | FCCP
370-86-5
|
$32.00-83.00 | 99.38% | 10g | TargetMol Chemicals Inc. | ||
 |
2024-06-13 | FCCP
370-86-5
|
$1.00 | 1KG | 99% | 20T | Shaanxi Dideu Medichem Co. Ltd | |
 |
2019-07-10 | carbonyl cyanide p-trifluoromethoxyphenylhydrazone
370-86-5
|
$8.80 | 1KG | 97%-99% | 100kg | Career Henan Chemical Co |
-
- FCCP
370-86-5
- $32.00-83.00
- 99.38%
- TargetMol Chemicals Inc.
-
- FCCP
370-86-5
- $1.00
- 99%
- Shaanxi Dideu Medichem Co. Ltd
-
- carbonyl cyanide p-trifluoromethoxyphenylhydrazone
370-86-5
- $8.80
- 97%-99%
- Career Henan Chemical Co
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