| Identification | More | [Name]
TRIS(2-CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE | [CAS]
51805-45-9 | [Synonyms]
3,3',3''-PHOSPHINETRIYL-TRIPROPIONIC ACID HYDROCHLORIDE
3,3',3''-PHOSPHINIDYNE-TRIPROPIONIC ACID HYDROCHLORIDE
TCEP
TCEP HCL
TCEP*HCL
TCEP, HYDROCHLORIDE
TRI(2-CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE
TRIS(2-CARBOXYETHYL)PHOSPHINE, HCL
TRIS(2-CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE
TRIS(CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE
TRIS(CARBOXYETHYL)PHOSPHINE &
0.5M TCEP
TRIS(2-CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE 99%
TRIS-(2-CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE (TCEP HCL)
Tris(2-carboxyethyl)phosphine-D16DCl
Tris-(2-carboxyethy)phosphine hydrochloride
Tris(2-carboxyethyl)phosphine,hydrochloride,99%
Tris(2-carboxyethyl)phosphonium Hydrochloride
TRIS-(2-CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE (TCEP)
3,3',3''-Phosphinidynetrispropanoic Acid Hydrochloride | [EINECS(EC#)]
629-759-1 | [Molecular Formula]
C9H16ClO6P | [MDL Number]
MFCD00145469 | [Molecular Weight]
286.65 | [MOL File]
51805-45-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
177 °C | [density ]
1.041 g/mL at 25 °C
| [refractive index ]
n20/D 1.367
| [storage temp. ]
2-8°C
| [solubility ]
H2O: 50 mg/mL
| [form ]
powder
| [pka]
7.66(at 25℃) | [color ]
white
| [PH]
7.0(aqueous solution; pH was adjusted with ammonium hydroxide) | [Water Solubility ]
Soluble in water and methanol. | [Sensitive ]
Moisture Sensitive | [Usage]
Biochemical tool for selective reduction of disulfide bridges at low pH; reductant for redox assay | [λmax]
λ: 260 nm Amax: 0.05
λ: 280 nm Amax: 0.03 | [Merck ]
14,9085 | [BRN ]
3724376 | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 1 month. | [InChIKey]
PBVAJRFEEOIAGW-UHFFFAOYSA-N | [CAS DataBase Reference]
51805-45-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
C,Xi | [Risk Statements ]
R36/38:Irritating to eyes and skin .
R36/37/38:Irritating to eyes, respiratory system and skin .
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S27:Take off immediately all contaminated clothing . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
2
| [F ]
10 | [TSCA ]
No | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Description]
TCEP HCl (51805-45-9) is a reagent for selective reduction of disulfides in aqueous solutions1-3?with distinct advantages over DTT which are application specific3. For example, spin labels are more stable with TCEP than DTT, Ni2+?(leached from affinity columns) causes rapid oxidation of DTT with no effect on TCEP and for long term storage of proteins TCEP is more stable than DTT with no metal chelator (EGTA) present but DTT is more stable in the presence of metal chelators.3 | [Chemical Properties]
White Crystalline Solid | [Uses]
Biochemical tool for selective reduction of disulfide bridges at low pH; reductant for redox assays. | [Uses]
TCEP (Tris(2-carboxyethyl)phosphine hydrochloride) is an alternative which is not pungent, more stable and works even at low pH. It is more selective, i.e. do not reduce metals and buried disulfides. | [Preparation]
The preparation of Tris(2-carboxyethyl)phosphine hydrochloride is as follows:Trimethyl 3,3 ', 3 "-phosphine triphenylpropionate (92.5g, 0.28mol) prepared as described above was added to a 250 ml reaction flask under mechanical stirring conditions and a molar ratio of 12mol/(120ml, 1.44mol), the mixture was heated to 90°C, the solid gradually dissolved, continue to heat the reaction 4h, stirring and cooling with ice water, precipitation of white solid, filter, filter cake with distilled water to get white (2-carboxyethyl) phosphine hydrochloride, dried, weighing 61.3g, yield 82.4% | [General Description]
Tris (2-carboxyethyl) phosphine (TCEP) is very effective in cleaving disulfide bonds in aqueous solution. It dissolves in water and is odorless, unlike other trialkylphosphines (tributylphosphine). It is also less toxic than 2-mercaptoethanol. These advantages make it better than the other reducing agents. | [Reactivity Profile]
Nucleophilic Substitution by the Phosphorus Atom of TCEP. 1. The phosphorus atom attacks one sulfur atom along the S-S bond. 2. A thioalkoxyphosphonium cation and a sulfhydryl anion are formed. 3. A rapid hydrolysis releases the second sulfhydryl molecule and the phosphine oxide. There are two main steps in the breaking of disulfide bridges and forming a free sulfhydryl using TCEP: cleavage of the S-S bond; oxidation of the phosphine and release of sulfhydryl.
| [Biochem/physiol Actions]
Tris(2-carboxyethyl)phosphine hydrochloride solution reduces the disulfide bonds and leaves other functional groups intact in proteins. | [storage]
Following reconstitution, aliquot and freeze (-20°C). TCEP retains stability when stored at an acidic or alkaline pH; avoid storage at pH 7.0-8.0. Also avoid exposure to high concentrations of phosphate ions (>150 mM). Stock solutions are stable for up to 3 months at -20°C. | [References]
1) Fischer?et al.?(1993),?In situ reduction suitable for matrix-assisted laser desorption/ionization and liquid secondary ionization using tris(2-carboxyethyl)phosphine; Rapid Commun. Mass Spectrom.,?7?225
2) Kirley?et al.?(1989),?Reduction and fluorescent labeling of cyst(e)ine-containing proteins for subsequent structural analysis; Anal. Biochem.,?180?231
3) Getz?et al. (1999),?A comparison between the sulfhydryl reductants tris(2-carboxyethyl)phosphine and dithiothreitol for use in protein biochemistry; Anal. Biochem.,?273?73 |
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