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D8130

5,5′-Dithiobis(2-nitrobenzoic acid)

Name: 5,5′-Dithiobis(2-nitrobenzoic acid)
Brand: SIGMA

BioReagent, ≥98%, suitable for determination of sulfhydryl groups

Synonym(s):

3-Carboxy-4-nitrophenyl disulfide, 6,6′-Dinitro-3,3′-dithiodibenzoic acid, Bis(3-carboxy-4-nitrophenyl) disulfide, DTNB, Ellman’s Reagent

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About This Item

Linear Formula:

[-SC₆H₃(NO₂)CO₂H]₂

CAS Number:

69-78-3

Molecular Weight:

396.35

Beilstein:

1896821

EC Number:

200-714-4

MDL number:

MFCD00007140

UNSPSC Code:

12352106

PubChem Substance ID:

24894189

NACRES:

NA.26

product line

BioReagent

Quality Level

200

Assay

≥98%

form

powder

mp

240-245 °C (dec.) (lit.)

suitability

suitable for determination of sulfhydryl groups

SMILES string

OC(=O)c1cc(SSc2ccc(c(c2)C(O)=O)[N+]([O-])=O)ccc1[N+]([O-])=O

InChI

1S/C14H8N2O8S2/c17-13(18)9-5-7(1-3-11(9)15(21)22)25-26-8-2-4-12(16(23)24)10(6-8)14(19)20/h1-6H,(H,17,18)(H,19,20)

InChI key

KIUMMUBSPKGMOY-UHFFFAOYSA-N

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General description

5,5′-Dithiobis(2-nitrobenzoic acid) is also called DTNB or Ellman′s reagent. It is a water soluble reagent, which interacts with thiol groups, and can be used conveniently at neutral pH. Thiolate anion (RS^-) reacts with Ellman′s reagent (DTNB^2-), to produce 2-nitro-5-thiobenzoate anion (TNB^2-) and one mixed disulfide (R-S-TNB^-). TNB^2- has a high molar absorption coefficient, and absorbs at 412nm. This absorption is independent of pH, at pH> 7.3.

Application

Ellman′s reagent maybe used for acetylcholinesterase assay, and to specifically label cysteine residues. It is a sensitive reagent for measuring the free sulfhydryl content in proteins, peptides, and tissues.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Gene therapy delivering a paraoxonase 1 variant offers long-term prophylactic protection against nerve agents in mice.

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Science translational medicine, 12(527) (2020-01-24)

Chemical warfare nerve agents are organophosphorus chemical compounds that induce cholinergic crisis, leaving little or no time for medical intervention to prevent death. The current chemical treatment regimen may prevent death but does not prevent postexposure complications such as brain

Staphylococcal extracellular adherence protein induces platelet activation by stimulation of thiol isomerases.

Anne Bertling et al.

Arteriosclerosis, thrombosis, and vascular biology, 32(8), 1979-1990 (2012-04-28)

Staphylococcus aureus can induce platelet aggregation. The rapidity and degree of this correlates with the severity of disseminated intravascular coagulation, and depends on platelet peptidoglycans. Surface-located thiol isomerases play an important role in platelet activation. The staphylococcal extracellular adherence protein

Quick measurement of protein sulfhydryls with Ellman's reagent and with 4,4'-dithiodipyridine.

Christian K Riener et al.

Analytical and bioanalytical chemistry, 373(4-5), 266-276 (2002-07-12)

Since its introduction in 1959, Ellman's reagent (5,5'-dithio-bis(2-nitrobenzoic acid)) has been the favorite reagent for spectrophotometric measurement of protein sulfhydryls. Meanwhile however, evidence has accumulated that many protein sulfhydryls give an incomplete reaction with Ellman's reagent, even during prolonged assay

Reassessment of Ellman's reagent.

P W Riddles et al.

Methods in enzymology, 91, 49-60 (1983-01-01)

Ellman's reagent: 5,5'-dithiobis(2-nitrobenzoic acid)--a reexamination.

P W Riddles et al.

Analytical biochemistry, 94(1), 75-81 (1979-04-01)

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Protocols

Enzymatic Assay of Chloramphenicol Acetyltransferase

To measure chloramphenicol acetyltransferase activity, this procedure uses DTNB and coenzyme A. The reaction of DTNB with the –SH group on CoA results in a colorimetric increase at 412 nm.

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