3-[bis(2-carboxyethyl)phosphanyl]propanoic acid hydrochloride

• ChemBase ID: 144570
• Molecular Formular: C9H16ClO6P
• Molecular Mass: 286.646501
• Monoisotopic Mass: 286.03730254
• SMILES: C(CP(CCC(=O)O)CCC(=O)O)C(=O)O.Cl
• Canonical SMILES: OC(=O)CCP(CCC(=O)O)CCC(=O)O.Cl
• InChI: InChI=1S/C9H15O6P.ClH/c10-7(11)1-4-16(5-2-8(12)13)6-3-9(14)15;/h1-6H2,(H,10,11)(H,12,13)(H,14,15);1H
• InChIKey: PBVAJRFEEOIAGW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[bis(2-carboxyethyl)phosphanyl]propanoic acid hydrochloride
• IUPAC Traditional name: tris(2-carboxyethyl)phosphine hydrochloride
• Synonyms: TCEP; Tris(2-carboxyethyl)phosphine hydrochloride; 3,3',3''-Phosphinidynetrispropanoic Acid Hydrochloride; Tris(2-carboxyethyl)phosphine Hydrochloride; Tris(carboxyethyl)phosphine Hydrochloride; TCEP Hydrochloride; Tris(2-carboxyethyl)phosphine hydrochloride solution; 三(2-羧乙基)膦 盐酸盐; 三(2-甲酰乙基)膦盐酸盐; 三(2-羧乙基)膦 盐酸盐 溶液

Database IDs

• CAS Number: 51805-45-9
• MDL Number: MFCD00145469
• Beilstein Number: 3724376
• Merck Index: 149085
• PubChem SID: 24883469; 24892716; 24889823; 162238782
• PubChem CID: 2734570

CALCULATED PROPERTIES

• Acid pKa: 3.2212362
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -6.017164
• LogD (pH = 7.4): -10.102781
• Log P: -1.2397103
• Molar Refractivity: 59.157 cm^3
• Polarizability: 21.855902 Å^3
• Polar Surface Area: 111.9 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble1 M, clear, colorless (no residue); H2O: soluble50 mg/mL; Methanol; Soluble in water; Water
• Apperance: Crystalline powder; white powder; White Solid
• Melting Point: 169-172°C; 177-178°C
• Density: 1.041 g/mL at 25 °C
• Refractive Index: n20/D 1.367
• Absorption Wavelength: λ: 260 nm Amax: 0.05; λ: 280 nm Amax: 0.03
• pH: 1.2-1.5; 7.0

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: 3261; UN3261
• German water hazard class: 2
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34; 36
• Safety Statements: 26; 26-27-36/37/39; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H314; H314-H318; H315-H319
• GHS Precautionary statements: P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P308+P313; P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%; ≥98% (NMR); ≥98.0% (C); 98%
• Concentration: 0.5 M
• Grade: purum
• Impurities: ≤0.5% water
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.05 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: sulfate (SO42-): ≤50 mg/kg
• Loss on Drying: ≤1.0% loss on drying
• λ: 0.1 M in H2O
• Product Line: BioUltra
• Empirical Formula (Hill Notation): C9H15O6P · HCl

DETAILS

Sigma Aldrich - 646547

Packaging
1, 10×1 mL in ampule
Application
TCEP is an effective reducing agent for protein analysis. As a non-mercaptan reducing agent, it avoids the toxicity inherent in thiol-containing compounds. It is capable of disrupting the botulinum neurotoxin B heavy-chain/light-chain complex that is held together by a single disulfide bond, and that is responsible for endocytosis, and ultimately the toxicity, of the toxin. Since disulfide-coupled subunits are characteristic of many toxins (e.g., ricin, snake venom, and all BoNT serotypes), it may be useful as a rescue prophylactic in cases of toxin administration.1

Sigma Aldrich - 75259

Application
Water soluble reagent, used for selective reduction of disulfides.1 More stable than DTT and useful in mass spectrometry applications.

Sigma Aldrich - C4706

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Reagent for the selective reduction of disulfides in water.1
Water soluble reagent, used for selective reduction of disulfides. More stable than DTT and useful in mass spectrometry applications.
When basified, this water-soluble ligand allows for simple removal of ruthenium-derived metathesis catalysts via aqueous washing of a crude reaction mixture.
Packaging
2, 10 g in glass bottle

Sigma Aldrich - 93284

Application
Water soluble reagent, used for selective reduction of disulfides.1 More stable than DTT and useful in mass spectrometry applications.

Toronto Research Chemicals - T012500

Biochemical tool for selective reduction of disulfide bridges at low pH; reductant for redox assay.

REFERENCES

• Neuburger, M., et al.: Eur. J. Biochem., 267, 2882 (2000)
• Krijt, J., et al.: Clin. Chem., 47, 1821 (2000)
• Yen, T.-Y., et al.: J. Mass Spectrom., 37, 15 (2000)