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C4706 Aldrich

Tris(2-carboxyethyl)phosphine hydrochloride

powder, ≥98%

Synonym: TCEP



Related Categories Cell Lysis and Protein Extraction Reagents, Chemical Modification Reagents, Chemical Synthesis, Molecular Biology, Native Protein Sample Preparation,
assay   ≥98%
form   powder
color   white
solubility   H2O: soluble50 mg/mL
storage temp.   2-8°C


Frequently Asked Questions

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Water soluble reagent, used for selective reduction of disulfides.4 More stable than DTT and useful in mass spectrometry applications.

Reagent for the selective reduction of disulfides in water.1

Tris(2-carboxyethyl)phosphine hydrochloride (TCEP.HCl) may be employed as catalyst for the reduction of sulfoxides, sulfonyl chlorides, N-oxides, and azides.1 It may be used as reducing agent for the reduction of various alkyl disulfides such as trans-4,5-dihydroxy-1,2-dithiane.2

When basified, this water-soluble ligand allows for simple removal of ruthenium-derived metathesis catalysts via aqueous washing of a crude reaction mixture.


2, 10, 50 g in glass bottle

General description

Tris(2-carboxyethyl)phosphine hydrochloride (TCEP.HCl) is a non-volatile solid. It is a strong reducing agent.12 It can be synthesized by the acid hydrolysis of tris(2-cyanoethyl)phosphine in refluxing aqueous HCl.12 It has various biological applications such as in vitro and in vivo reduction of disulfide bonds in various peptides and proteins.1 TCEP is a useful chelating agent for various heavy metal ions as Zn(II), Cd(II), Pb(II), and Ni(II).3

Price and Availability

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Tris(2-<WBR>carboxyethyl)<WBR>phosphine hydrochloride

BioUltra, for electrophoresis, SDS-PAGE tested

Tris(2-<WBR>carboxyethyl)<WBR>phosphine hydrochloride solution

0.5 M, pH 7.0(aqueous solution; pH was adjusted with ammonium hydroxide)

Safety & Documentation

Safety Information

GHS05  GHS05
Signal word 
Hazard statements 
Precautionary statements 
UN 3261 8 / PGII
WGK Germany 
Protocols & Articles
Peer-Reviewed Papers


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1. Burns, J. A., et al. J. Org. Chem. 56, 1648, (1991)

2. Selective reduction of disulfides by tris (2-carboxyethyl) phosphine. Burns JA, et al. J. Org. Chem. 56(8), 2648-2650, (1991)

3. Coordination properties of tris (2-carboxyethyl) phosphine, a newly introduced thiol reductant, and its oxide. Krezel A, et al. Inorg. Chem. 42(6), 1994-2003, (2003)

4. Burns, J.A. J. Org. Chem. 56, 2648, (1991)

In situ reduction suitable for matrix-assisted laser desorption/ionization and liquid secondary ionization using tris(2-carboxyethyl)phosphine. Fischer W.H, et al. Rapid Commun. Mass Spectrom. 7, 225-228, (1993)


Reduction and fluorescent labeling of cyst(e)ine-containing proteins for subsequent structural analyses. Kirley, T.L. Anal. Biochem. 180, 231-236, (1989)


A comparison between the sulfhydryl reductants tris(2-carboxyethyl)phosphine and dithiothreitol for use in protein biochemistry. Getz, et al. Anal. Biochem. 273, 73-80, (1999)


Maynard, H. D.; Grubbs, R. J. Tetrahedron Lett. 40, 4137, (1999)

Grubbs, R. H. Org. React. 22, 123, (2004)

Diagnostic nanoparticle targeting of the EGF-receptor in complex biological conditions using single-domain antibodies. Zarschler K, Prapainop K, Mahon E, et al. Nanoscale 6(11), 6046-56, (2014)


Aminopeptidase P3, a new member of the TNF-TNFR2 signaling complex, induces phosphorylation of JNK1 and JNK2. Inoue M, Kamada H, Abe Y, et al. J. Cell Sci. 128(4), 656-69, (2015)


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Injectable Peptide Decorated Functional Nanofibrous Hollow Microspheres to Direct Stem Cell Differentiation and Tissue Regeneration. Zhang Z, Gupte MJ, Jin X, et al. Adv. Funct. Mater. 25(3), 350-360, (2015)


Unfolding and aggregation of a glycosylated monoclonal antibody on a cation exchange column. Part II. Protein structure effects by hydrogen deuterium exchange mass spectrometry. Guo J, Carta G, et al. J. Chromatogr. A. 1356, 129-37, (2014)


ERK-mediated phosphorylation of TFAM downregulates mitochondrial transcription: implications for Parkinson's disease. Wang KZ, Zhu J, Dagda RK, et al. Mitochondrion 17, 132-40, (2014)


Use of elemental and molecular-mass spectrometry to assess the toxicological effects of inorganic mercury in the mouse Mus musculus. García-Sevillano MA, García-Barrera T, Navarro F, et al. Anal. Bioanal. Chem 406(24), 5853-65, (2014)


Analysis of telomerase activity based on a spired DNA tetrahedron TS primer. Li Y, Wen Y, Wang L, et al. Biosens. Bioelectron. 67, 364-9, (2015)


Detecting multiple cell-secreted cytokines from the same aptamer-functionalized electrode. Liu Y, Liu Y, Matharu Z, et al. Biosens. Bioelectron. 64, 43-50, (2014)


A novel mechanism of autophagic cell death in dystrophic muscle regulated by P2RX7 receptor large-pore formation and HSP90. Young CN, Sinadinos A, Lefebvre A, et al. Autophagy 11(1), 113-30, (2015)


Targeted intracellular delivery of proteins with spatial and temporal control. Morales DP, Braun GB, Pallaoro A, et al. Mol. Pharm. 12(2), 600-9, (2015)


Insights into autophagosome maturation revealed by the structures of ATG5 with its interacting partners. Kim JH, Hong SB, Lee JK, et al. Autophagy 11(1), 75-87, (2015)


Structures of multidomain proteins adsorbed on hydrophobic interaction chromatography surfaces. Gospodarek AM, Sun W, O'Connell JP, et al. J. Chromatogr. A. 1371, 204-19, (2014)


Novel pyridinium-based tags: synthesis and characterization for highly efficient analysis of thiol-containing peptides by mass spectrometry. Qiao X, Yang Y, Liu S, et al. Analyst 140(2), 407-13, (2014)


Absolute quantification of superoxide dismutase in cytosol and mitochondria of mice hepatic cells exposed to mercury by a novel metallomic approach. García-Sevillano MA, García-Barrera T, Navarro F, et al. Anal. Chim. Acta 842, 42-50, (2014)


Fluorescence study of domain structure and lipid interaction of human apolipoproteins E3 and E4. Mizuguchi C, Hata M, Dhanasekaran P, et al. Biochim. Biophys. Acta 1841(12), 1716-24, (2015)


Development and analytical comparison of microflow and nanoflow liquid chromatography/mass spectrometry procedures for quantification of cardiac troponin T in mouse hearts. Olkowicz M, Rybakowska I, Chlopicki S, et al. Talanta 131, 510-20, (2014)


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In Salmonella enterica, the Gcn5-related acetyltransferase MddA (formerly YncA) acetylates methionine sulfoximine and methionine sulfone, blocking their toxic effects. Hentchel KL and Escalante-Semerena JC J. Bacteriol. 197(2), 314-25, (2015)


Cell-free identification of novel N-myristoylated proteins from complementary DNA resources using bioorthogonal myristic acid analogues. Takamitsu E, Fukunaga K, Iio Y, et al. Anal. Biochem. 464, 83-93, (2014)


Synthesis of lucifensin by native chemical ligation and characteristics of its isomer having different disulfide bridge pattern. Stanchev S, Zawada Z, Monincová L, et al. J. Pept. Sci. 20(9), 725-35, (2014)


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Merck 14,9085

Beil. 4,IV,3441


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