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Merck

D8130

5,5′-Dithiobis(2-nitrobenzoic acid)

≥98%, BioReagent, 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
UNSPSC Code:
12352106
NACRES:
NA.26
PubChem Substance ID:
24894189
EC Number:
200-714-4
Beilstein/REAXYS Number:
1896821
MDL number:
MFCD00007140

Key Documents

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Product Name

5,5′-Dithiobis(2-nitrobenzoic acid), ≥98%, BioReagent, suitable for determination of sulfhydryl groups

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)

SMILES string

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

InChI key

KIUMMUBSPKGMOY-UHFFFAOYSA-N

product line

BioReagent

assay

≥98%

form

powder

mp

240-245 °C (dec.) (lit.)

suitability

suitable for determination of sulfhydryl groups

Quality Level

200

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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.

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 (DTNB2-), to produce 2-nitro-5-thiobenzoate anion (TNB2-) and one mixed disulfide (R-S-TNB-). TNB2- has a high molar absorption coefficient, and absorbs at 412nm. This absorption is independent of pH, at pH> 7.3.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD6810V
WXBD2033V
WXBD5644V
WXBD5214V
MKCL9148

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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)
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)
Baharan Emam et al.
Particle and fibre toxicology, 17(1), 8-8 (2020-01-31)
Epidemiological studies have reported associations between elevated air pollution and autism spectrum disorders (ASD). However, we hypothesized that exposure to air pollution that mimics real world scenarios, is a potential contributor to ASD. The exact etiology and molecular mechanisms underlying
Venkaiah Betapudi et al.
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
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