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;Phalloidin from Amanita phalloides
- CBNumber
- CB6458766
- Molecular Formula
- C35H48N8O11S
- Formula Weight
- 788.87
- MOL File
- 17466-45-4.mol
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
- biological source
- Amanita phalloides
- optical activity
- +62.3 (Ethanol)
- Water Solubility
- Soluble to 1 mg/ml in water
- Merck
- 13,7273
- BRN
- 4347460
- Sequence
- Ala-{d-Thr}-Cys-{Hyp}-Ala-Trp-Leu (Sulfide bridge: Cys3-Trp6)
- Stability:
- Stable. Incompatible with strong oxidizing agents.
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
- F
- 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)
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.
N-Bromosuccinimide Price
- Product number
- P2141
- Product name
- Phalloidin from Amanita phalloides
- Purity
- ≥90%
- Packaging
- 1mg
- Price
- $311
- Updated
- 2025/07/31
- Product number
- 18039
- Product name
- Phalloidin
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $220
- Updated
- 2024/03/01
- Product number
- 4535
- Product name
- Phalloidin
- Packaging
- 1
- Price
- $236
- Updated
- 2021/12/16
- Product number
- P294523
- Product name
- Phalloidine
- Packaging
- 100μg
- Price
- $80
- Updated
- 2021/12/16
- Product number
- 462347
- Product name
- Phalloidine
- Packaging
- 100μg
- Price
- $355
- Updated
- 2021/12/16
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
References
[1] E WULF. Fluorescent phallotoxin, a tool for the visualization of cellular actin.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1979, 76 9: 4498-4502. DOI: 10.1073/pnas.76.9.4498
[2] MUHAMMAD RAIHAN JUMAT. Imaging analysis of human metapneumovirus-infected cells provides evidence for the involvement of F-actin and the raft-lipid microdomains in virus morphogenesis.[J]. Virology Journal, 2014, 11: 198. DOI: 10.1186/s12985-014-0198-8
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