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Tris(2-carboxyethyl)phosphine hydrochloride

Name: Tris(2-carboxyethyl)phosphine hydrochloride
Brand: SIGMA

BioUltra, suitable for electrophoresis, SDS-PAGE tested

Synonym(s):

TCEP.HCL, TCEP

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₅O₆P · HCl

CAS Number:

51805-45-9

Molecular Weight:

286.65

UNSPSC Code:

12352128

NACRES:

NA.32

PubChem Substance ID:

329761275

MDL number:

MFCD00145469

Beilstein/REAXYS Number:

3724376

Assay:

97.5-102.5%

Form:

powder

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Properties

product line

BioUltra

Quality Segment

100

assay

97.5-102.5%

form

powder

mol wt

286.65 g/mol

concentration

90-100 % (w/w) (Tris(2-carboxyethyl)phosphine hydrochloride)

technique(s)

electrophoresis: suitable

color

white

mp

175-177 °C

solubility

H₂O: soluble

density

1.041 g/cm³ at 25 °C

suitability

SDS-PAGE tested

SMILES string

Cl[H].OC(=O)CCP(CCC(O)=O)CCC(O)=O

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

InChI key

PBVAJRFEEOIAGW-UHFFFAOYSA-N

Description

General description

Tris(2-carboxyethyl) phosphine hydrochloride (TCEP.HCL ) is a useful reducing agent for Sulphur and nitrogen-containing compounds. TCEP.HCL and the resultant oxide are water-soluble. [1] TCEP.HCL has electron-rich phosphorus and oxygen atoms to combine with various metals, including Rh, Ir, and Pd. It rapidly complexes with Rh and Ir in dioxane at ambient temperature.[2] It reduces disulfide linkages in a range of peptides and proteins in biological disulfide.[1]

Application

TCEP.HCL has been used in various bioconjugation applications, both in vitro and in vivo, to tag proteins and live organisms with great effectiveness under mild physiological circumstances.[3] TCEP.HCL is suitable for varied biological and synthetic applications. At an acidic pH, TCEP.HCL can be used to convert organic disulfides to thiols in water irreversibly.[1]

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

Features and Benefits

The product has the following benefits:

TCEP.HCL lowers reactive oxygen species levels.[3]
It increases glutathione levels and mitochondrial content.[3]
It has anti-cancer effects.[2]

Analysis Note

agarose gel electrophorese corresponds to requirements

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This Item	C4706	580560	75259
Sigma-Aldrich 68957 Tris(2-carboxyethyl)phosphine hydrochloride	Sigma-Aldrich C4706 Tris(2-carboxyethyl)phosphine hydrochloride	Millipore 580560 TCEP, Hydrochloride	Sigma-Aldrich 75259 Tris(2-carboxyethyl)phosphine hydrochloride
assay 97.5-102.5%	assay -	assay ≥98% (elemental analysis)	assay ≥98% (NMR)
Quality Level 100	Quality Level 300	Quality Level 100	Quality Level 300
solubility H₂O: soluble	solubility H₂O: 50 mg/mL	solubility water: 5 mg/mL	solubility H₂O: 1 M, clear, colorless (no residue)
form powder	form powder	form crystalline solid	form crystals
mp 175-177 °C	mp 175-177 °C	mp -	mp -
density 1.041 g/cm³ at 25 °C	density 1.041 g/cm³ at 25 °C	density -	density -

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Explore all of our products under Tris(2-carboxyethyl)phosphine hydrochloride

pictograms

GHS05

signalword

Danger

hcodes

H314

pcodes

P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 1

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Synthesis and characterization of a novel class of reducing agents that are highly neuroprotective for retinal ganglion cells.

Christopher R Schlieve et al.

Experimental eye research, 83(5), 1252-1259 (2006-08-29)

Retinal ganglion cells (RGCs) undergo apoptosis after axonal injury, in part regulated by an intracellular superoxide anion burst, for which the target(s) are unknown. Shifting the RGC redox state towards reduction and preventing sulfhydryl oxidation is neuroprotective in vitro and

In situ reduction suitable for matrix-assisted laser desorption/ionization and liquid secondary ionization using tris(2-carboxyethyl)phosphine.

W H Fischer et al.

Rapid communications in mass spectrometry : RCM, 7(3), 225-228 (1993-03-01)

The suitability of the hydrochloride salt of tris(2-carboxyethyl)phosphine (TCEP) for in situ reduction with matrix-assisted laser desorption/ionization (MALDI) and liquid secondary ionization (LSI) mass spectrometry is evaluated. TCEP can be used to irreversibly reduce organic disulfides to thiols in water

Effects of tris (2-carboxyethyl) phosphine hydrochloride treatment on porcine oocyte in vitro maturation and subsequent in vitro fertilized embryo developmental capacity.

Yiren Zeng et al.

Theriogenology, 162, 32-41 (2021-01-15)

Oocyte in vitro maturation (IVM) is a crucial process that determines subsequent in vitro embryo production. The present study investigated the effects of the antioxidant tris (2-carboxyethyl) phosphine hydrochloride (TCEP-HCL) on the in vitro maturation of porcine oocytes and in vitro developmental competence of

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Global Trade Item Number

SKU	GTIN
68957-10G	04061838351777

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