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PHALLOIDIN

Product Name
PHALLOIDIN
CAS No.
17466-45-4
Chemical Name
PHALLOIDIN
Synonyms
Nsc523214;PHALLOIDIN;phalloidine;Glycerol Formal Impurity 5;Phalloidin *CAS#: 17466-45-4*;PHALLOIDIN, AMANITA PHALLOIDES;Phalloidin trifluoroacetate salt;PHALLOIDIN FROM AMANITA PHALLOIDES;Phalloidin, 90%, from Amanita phalloides;pto-l-tryptophyl-4,5-dihydroxy-l-leucyl),cyclic(3,6)-sulfide
CBNumber
CB6458766
Molecular Formula
C35H48N8O11S
Formula Weight
788.87
MOL File
17466-45-4.mol
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PHALLOIDIN Property

Melting point:
280-282°
alpha 
+55.7°(D/20℃)(c=0.5,メタノール)
Density 
1.1612 (rough estimate)
refractive index 
1.7400 (estimate)
storage temp. 
+2C to +8C
solubility 
DMF: 10 mg/ml; DMSO: 10 mg/ml; Ethanol: 10 mg/ml; Water: 0.5 mg/ml (warm)
form 
White crystalline solid
Boiling point:
1370.5±65.0 °C(Predicted)
pka
13.03±0.70(Predicted)
color 
Hexahydrate, needles or crystals from water
Water Solubility 
Soluble to 1 mg/ml in water
Merck 
13,7273
BRN 
4347460
Stability:
Stable. Incompatible with strong oxidizing agents.
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Safety

Hazard Codes 
T+
Risk Statements 
26/27/28
Safety Statements 
22-28-36/37-45
RIDADR 
UN 3462 6.1/PG 2
WGK Germany 
3
RTECS 
SE9800000
18
HazardClass 
6.1(a)
PackingGroup 
I
HS Code 
2934999090
Hazardous Substances Data
17466-45-4(Hazardous Substances Data)
Toxicity
LD50 i.m. in albino mice: 3.3 mg/g (Vogt); LD50 i.p. in mice: 2 mg/kg (Wieland, Wieland)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Precautionary statements

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

P262Do not get in eyes, on skin, or on clothing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
P2141
Product name
Phalloidin from Amanita phalloides
Purity
≥90%
Packaging
1mg
Price
$181.2
Updated
2024/03/01
Cayman Chemical
Product number
18039
Product name
Phalloidin
Purity
≥98%
Packaging
1mg
Price
$220
Updated
2024/03/01
Tocris
Product number
4535
Product name
Phalloidin
Packaging
1
Price
$236
Updated
2021/12/16
Usbiological
Product number
462347
Product name
Phalloidine
Packaging
100μg
Price
$355
Updated
2021/12/16
Usbiological
Product number
256230
Product name
Phalloidin
Packaging
1mg
Price
$495
Updated
2021/12/16
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PHALLOIDIN Chemical Properties,Usage,Production

Description

Phalloidin is a natural mycotoxin first isolated from the death cap mushroom, A. phalloides. It binds F-actin and stabilizes actin fibers. Fluorescently labeled phalloidin is commonly used to stain F-actin in cells.

Chemical Properties

white powder

Uses

Phalloidin has been used:

  • As a supplement in PEM buffer and dimethyl sulfoxide (DMSO).
  • As a drug.
  • In immunohistochemistry to stain F-actin.

Definition

ChEBI: A homodetic bicyclic heptapeptide having a sulfide bridge.

General Description

Phalloidin is a phallotoxin produced by death cap mushroom Amanita phalloides. It is a cyclic peptide, which interacts with actin, and this was first identified in phalloidin-poisoned rats. It is a heptapeptide, cyclic in nature, with a crosslink between tryptophan at position 6 and cysteine at position 3. The side chain of amino acid 7 (γ-δ-dihydroxyleucine) in phalloidin, is accessible to modifications, through which fluorescently labeled phalloidin compounds can be produced.

Biochem/physiol Actions

Toxin that binds polymeric F actin, stabilizing it and interfering with the function of actin-rich structures.

Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. Mutation data reported. Whenheated to decomposition it emits toxic fumes of SOx, and NOx.

Enzyme inhibitor

This bicyclic heptapeptide toxin (FW = 788.88 g/mol; CAS 17466-45-4) is was first isolated from the poisonous green fungus Amanita phalloides. Primary Mode of Action: Phalloidin binds preferentially to filamentous actin; little or no binding to globular actin has been detected. such preferential action stimulates actin polymerization, and phalloidin lowers the actin monomer critical concentration by 30x, from 50-100 nM down to 2-3 nM. When present at 1 to 10 concentration ratio of phalloidin to total actin subunits, actin filaments are also greatly stabilized toward depolymerization. Effects on Actin Filaments: Cellular processes requiring filament disassembly are likewise inhibited. Depolymerization of F-actin by cytochalasins, potassium iodide, and elevated temperatures are inhibited by phalloidin binding. Because the toxin and its fluorescent derivatives are relatively small, a wide variety of actin-binding proteins can still bind to phalloidin-labeled filamentts. Perhaps more significantly, phalloidin-labeled actin filaments retain many of their functional properties, such that phalloidin-labeled, glycerinated muscle fibers can still contract, and labeled actin filaments still move on myosin that has been tethered to solid-phase substrates. Phalloidin can be also be used to assess the relativeconcentrations of these two forms of actin as well as a means to label actin filaments in a cell (See Phallacidin).

storage

Store at -20°C

PHALLOIDIN Preparation Products And Raw materials

Raw materials

Preparation Products

17466-45-4, PHALLOIDINRelated Search:


  • Phalloidin, Amanita phalloides - CAS 17466-45-4 - Calbiochem
  • Phalloidin trifluoroacetate salt
  • pto-l-tryptophyl-4,5-dihydroxy-l-leucyl),cyclic(3,6)-sulfide
  • PHALLOIDIN
  • PHALLOIDIN, AMANITA PHALLOIDES
  • PHALLOIDIN FROM AMANITA PHALLOIDES
  • Cyclo(L-Ala-D-Thr-L-Cys(1)-L-c4Hyp-L-Ala-L-Trp2(1)-4,5'-dihydroxy-L-Leu-)
  • Cyclic(L-alanyl-D-threonyl-L-cysteinyl-cis-4-hydroxy-L-prolyl-L-alanyl-2-mercapto-L-tryptophyl-4,5-dihydroxy-L-leucyl), cyclic (3.fwdarw.6)-sulfide
  • Nsc523214
  • cyclic(l-alanyl-d-threonyl-l-cysteinyl-cis-4-hydroxy-l-prolyl-l-alanyl-2-merca
  • phalloidine
  • Phalloidin *CAS#: 17466-45-4*
  • Phalloidin, 90%, from Amanita phalloides
  • Glycerol Formal Impurity 5
  • 17466-45-4
  • C35H48N8O11S
  • Cytoskeleton and Extracellular Matrix
  • Actin Inhibitors and Probes
  • BioChemical
  • Cell Signaling and Neuroscience
  • Cell Biology
  • marker