If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf
C4706
Tris(2-carboxyethyl)phosphine hydrochloride
powder
Synonym(s):
TCEP
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About This Item
Recommended Products
description
Protect from moisture
Quality Level
form
powder
reaction suitability
reagent type: reductant
color
white
solubility
H2O: 50 mg/mL
storage temp.
2-8°C
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
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Related Categories
General description
Application
- As a reducing agent for the reduction of sulfoxides, sulfonyl chlorides, N-oxides, and azides. It can also be used in azide-alkyne cycloaddition reaction in the presence of a copper catalyst.[3]
- To reduce disulfide bonds in various proteins.[3]
- As a reagent for the selective reduction of disulfides in water.[1]
- To remove ruthenium-derived metathesis catalysts via aqueous washing of a crude reaction mixture when it is basified.[4][5]
- As a reducing agent for the reduction of various alkyl disulfides such as trans-4,5-dihydroxy-1,2-dithiane.[1]
Caution
Related product
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk_germany
WGK 1
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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How can I determine the shelf life / expiration / retest date of this product?
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How is shipping temperature determined? And how is it related to the product storage temperature?
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Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf
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Hello, how long is a 0.5 M TCEP solution in water stable? Can it be stored at -80 °C or 4 °C? If so, for how long can it be kept at each temperature? Thanks.
1 answer-
This material is quite stable in solution. A prepared solution, 646547, 0.5 M TCEP, pH 7, notes that solutions are stable for up to 2 years at room temperature. The pH of the prepared solution is adjusted to 7.0 using ammonium hydroxide. Refrigeration of the solution is not expected to be harmful. However, the freeze/thaw process may be detrimental. Please see the link below to review the product datasheet for the prepared solution:
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/120/057/646547dat.pdfHelpful?
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I would like to use TCEP for the protein purification and enzyme activity purposes. What product do you recommend, please? I prefer powder formula. Thank you
1 answer-
TCEP is a very common reducing agent in protein analysis. All of the TCEP powder products reference protein applications. One product, 68957, is tested for use in protein electrophoresis, however none of the TCAP products are tested for suitability in enzyme assays. The end user would have to determine suitability. Please see the link below to the available product options:
https://www.sigmaaldrich.com/search/51805-45-9?focus=products&page=1&perpage=30&sort=relevance&term=51805-45-9&type=cas_numberPlease see the link below to review the available peer reviewed papers:
https://www.sigmaaldrich.com/search/tcep?focus=papers&page=1&perpage=30&sort=relevance&term=tcep&type=citation_searchHelpful?
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How long is this TCEP stable at 2-8C in powder form?
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This product will be stable at 2-8°C for 2 years from the date of release. It is assigned a recommended retest date of 2 years after the quality release date. This date is lot-specific and can be found on the Certificate of Analysis. A recommended retest date is the period of time during which the product is expected to remain within established stability specifications, provided that it has been stored under defined conditions. After the Retest Date, product samples should be examined to ensure that the product is still in compliance with the established specifications.
For more information, you may access the "Product Dating Information" document under "ADDITIONAL USEFUL DOCUMENTS ABOUT OUR PRODUCTS" at the bottom of the Quality Services page with this link: https://www.sigmaaldrich.com/US/en/life-science/quality-and-regulatory-management/quality-services.Helpful?
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What is Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride, soluble in?
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TCEP is soluble in water at 50 mg/ml and is also stable under both acidic and basic pH conditions. For work in protein analysis and mass spectrometry, we also offer an already prepared version of TCEP in a buffered aqueous solution. Product# 646547 is 0.5M solution of TCEP in water, where the pH has been adjusted to 7 with ammonium hydroxide.
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What is the Department of Transportation shipping information for this product?
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Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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What is the primary function of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride?
1 answer-
Tris (2-carboxyethyl) phosphine hydrochloride (TCEP, #C4706) is capable of selectively cleaving disulfide bonds.
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What is the benefit of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride (TCEP), over traditional disulfide reduction agents, like DTT (dithiothreitol) and BME (beta-mercaptoethanol)?
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TCEP is a very effective disulfide reducing agent that is less toxic than beta-mercaptoethanol and more stable to solution oxidation and pH changes than dithiothreitol.
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Where can I find protocols that cite the use of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride (TCEP)?
1 answer-
1. Burns, J. A., et al. J. Org. Chem. 56, 1648, (1991)2. Maynard, H. D.; Grubbs, R. J. Tet. Lett. 40, 4137, (1999)3. Grubbs, R. H. Org. React. 22, 123, (2004)4. Burns, J.A. J. Org. Chem. 56, 2648, (1991)5. Kirley, T.L., Reduction and fluorescent labeling of cyst(e)ine-containing proteins for subsequent structural analyses. Anal. Biochem. 180, 231-236, (1989)6. Fischer W.H, et al., In situ reduction suitable for matrix-assisted laser desorption/ionization and liquid secondary ionization using tris(2-carboxyethyl)phosphine. Rapid Commun. Mass Spectrom. 7, 225-228, (1993)7. Getz, E.B., et al., A comparison between the sulfhydryl reductants tris(2-carboxyethyl)phosphine and dithiothreitol for use in protein biochemistry. Anal. Biochem. 273, 73-80, (1999) 8. Beil. 4,IV,3441
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