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FCCP

FCCP structure

CAS No:
370-86-5
Formula:
C10H5F3N4O
Chemical Name:
FCCP
Synonyms:
Propanedinitrile,2-[2-[4-(trifluoromethoxy)phenyl]hydrazinylidene]-;Mesoxalonitrile,[p-(trifluoromethoxy)phenyl]hydrazone;Propanedinitrile,[[4-(trifluoromethoxy)phenyl]hydrazono]-;2-[2-[4-(Trifluoromethoxy)phenyl]hydrazinylidene]propanedinitrile;FCCP;Trifluoromethoxy carbonylcyanide phenylhydrazone;Carbonyl cyanide [p-(trifluoromethoxy)phenyl]hydrazone;Carbonyl cyanide [4-(trifluoromethoxy)phenyl]hydrazone;FCCCP;[[4-(Trifluoromethoxy)phenyl]hydrazono]malononitrile;2-[[4-(Trifluoromethoxy)phenyl]hydrazinylidene]propanedinitrile
Categories:
Chemical Reagents > Organic Reagents

Description

FCCP is an uncoupler of oxidative phosphorylation in mitochondria.

Carbonyl cyanide p-trifluoromethoxyphenylhydrazone is a hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group. It has a role as an ionophore, an ATP synthase inhibitor and a geroprotector. It is a hydrazone, a nitrile, an organofluorine compound and an aromatic ether. It derives from a hydrazonomalononitrile.|A proton ionophore that is commonly used as an uncoupling agent in biochemical studies.

FCCP Basic Attributes

Molecular Weight：

254.17

Exact Mass：

254.17

EC Number：

206-730-8

DSSTox ID：

DTXSID40190494

HScode：

2928000090

Characteristics

PSA：

81.2

XLogP3：

3.7

Appearance：

yellow powder

Density：

1.3±0.1 g/cm3

Melting Point：

174 °C (decomp)

Boiling Point：

293.3°C at 760 mmHg

Flash Point：

131.2±30.1 °C

Refractive Index：

1.522

Water Solubility：

acetone: 20 mg/mL, clear, very deep greenish yellow

Storage Conditions：

2-8°C

Safety Information

Packing level：

Hazard category：

6.1(a)

Transport codes：

UN 2811 6.1/PG 2

wgk germany：

hazard class code：

25-43

safety instructions：

36/37-45

RTECS Number：

FG5775000

Marks：

T,Xi

Hazard note：

Irritant

Precautionary statement(s)：

P280-P301 + P310

Hazard Statements：

H301-H317-H413

Drug Information

MeSH：

Chemical agents that increase the permeability of CELL MEMBRANES to PROTONS. (See all compounds classified as Proton Ionophores.)

MeSH Entry Terms：

(4-(Trifluoromethoxy)phenyl)hydrazonopropanedinitrile

FCCP Use and Manufacturing

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]

Computed Properties

Molecular Weight:254.17
XLogP3:3.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:3
Exact Mass:254.04154528
Monoisotopic Mass:254.04154528
Topological Polar Surface Area:81.2
Heavy Atom Count:18
Complexity:388
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes