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重要文件

C4706

Sigma-Aldrich

三 2-羰基乙基 磷盐酸盐 盐酸盐

Tris(2-carboxyethyl)phosphine hydrochloride
1 of 1 reviewers received a sample product or took part in a promotion

powder

同義詞:

TCEP

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About This Item

經驗公式(希爾表示法):
C9H15O6P · HCl
CAS號碼:
分子量::
286.65
Beilstein:
3724376
MDL號碼:
分類程式碼代碼:
12352128
PubChem物質ID:
NACRES:
NA.22
形狀:
powder
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描述

Protect from moisture

品質等級

形狀

powder

反應適用性

reagent type: reductant

顏色

white

溶解度

H2O: 50 mg/mL

儲存溫度

2-8°C

SMILES 字串

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 密鑰

PBVAJRFEEOIAGW-UHFFFAOYSA-N

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一般說明

三(2-羧乙基)膦盐酸(TCEP.HCl)是一种非挥发性的固体。它是一种强还原剂。1[1]可通过回流HCl水溶液水解三(2-氰基乙基)膦酸合成。1[1] 它支持多种生物学应用,如体外体内还原各种肽和蛋白质中的二硫键。TCEP是适于各种重金属离子的重要螯合剂,如Zn(II)、Cd(II)、Pb(II)和Ni(II)。[2]

應用

三(2-羧乙基)膦盐酸盐(TCEP.HCl)可用于:
  • 用作还原亚砜、磺酰氯、N-氧化物和叠氮化物的还原剂。存在铜催化剂的条件下,它还可用于叠氮化物-炔烃的环加成反应。[3]
  • 还原各种蛋白质中的二硫键。[3]
  • 用作选择性还原水中二硫化物的试剂。[1]
  • 碱化粗反应混合物时,通过水洗除去钌衍生的复分解催化剂。[4][5]
  • 用作还原各种烷基二硫键的还原剂,例如反式-4,5-二羟基-1,2-二噻烷。[1]
水溶性试剂,用于二硫化物的选择性还原。在质谱应用中比 DTT 更稳定。

注意

储存条件:干燥储存。

相關產品

象形圖

Corrosion

訊號詞

Danger

危險聲明

危險分類

Eye Dam. 1 - Skin Corr. 1B

儲存類別代碼

8A - Combustible corrosive hazardous materials

水污染物質分類(WGK)

WGK 1

個人防護裝備

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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分析證明 (COA)

Lot/Batch Number

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存取文件庫

Tris (2-carboxyethyl) phosphine Hydrochloride
Yost Julianne M et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-9 (2001)
Grubbs, R. H.
Org. React., 22, 123-123 (2004)
Selective reduction of disulfides by tris (2-carboxyethyl) phosphine.
Burns JA, et al.
The Journal of Organic Chemistry, 56(8), 2648-2650 (1991)
Selective reduction of disulfides by tris(2-carboxyethyl)phosphine
Burns, J. A., et al.
The Journal of Organic Chemistry, 56(8), 2648-2648 (1991)
Coordination properties of tris (2-carboxyethyl) phosphine, a newly introduced thiol reductant, and its oxide.
Krezel A, et al.
Inorganic Chemistry, 42(6), 1994-2003 (2003)

Questions

1–10 of 10 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. 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

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. 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

      Helpful?

  3. 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
    1. 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.pdf

      Helpful?

  4. 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
    1. 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_number

      Please 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_search

      Helpful?

  5. How long is this TCEP stable at 2-8C in powder form?

    1 answer
    1. 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?

  6. What is Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride, soluble in?

    1 answer
    1. 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.

      Helpful?

  7. What is the Department of Transportation shipping information for this product?

    1 answer
    1. 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.

      Helpful?

  8. What is the primary function of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride?

    1 answer
    1. Tris (2-carboxyethyl) phosphine hydrochloride (TCEP, #C4706) is capable of selectively cleaving disulfide bonds.

      Helpful?

  9. Where can I find protocols that cite the use of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride (TCEP)?

    1 answer
    1. 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

      Helpful?

  10. 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)?

    1 answer
    1. 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.

      Helpful?

Reviews

1 of 1 reviewers received a sample product or took part in a promotion

Active Filters

  1. Coventry, United Kingdom
    • Review 1
    • Votes 0
    5 out of 5 stars.

    Reliable product

    Good and reliable product of high quality. Great purity

    Helpful?

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