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373605

Sigma-Aldrich

6,6′-Dithiodinicotinic acid

technical grade, 85%

Synonym(s):

Bis[3-Carboxypyridine] 6,6′-disulfide, Bis[3-carboxypyridine] 6,6′-disulfide

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About This Item

Empirical Formula (Hill Notation):
C12H8N2O4S2
CAS Number:
15658-35-2
Molecular Weight:
308.33
EC Number:
239-729-6
MDL number:
MFCD00006454
UNSPSC Code:
12352100
PubChem Substance ID:
24863248
NACRES:
NA.22

grade

technical grade

Assay

85%

form

solid

mp

263-265 °C (lit.)

SMILES string

OC(=O)c1ccc(SSc2ccc(cn2)C(O)=O)nc1

InChI

1S/C12H8N2O4S2/c15-11(16)7-1-3-9(13-5-7)19-20-10-4-2-8(6-14-10)12(17)18/h1-6H,(H,15,16)(H,17,18)

InChI key

GSASOFRDSIKDSN-UHFFFAOYSA-N

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General description

6,6′-Dithiodinicotinic acid is reported as sulphydryl reagent. 6,6′-Dithiodinicotinic acid is reported to react with thiols, to afford a disulfide and 6-mercaptonicotinic acid. Interaction of 6,6′-dithiodinicotinic acid with the homogenates of Ehrlich ascites cells has been reported.

Application

6,6′-Dithiodinicotinic acid may be employed as:
  • specific thiol blocker to investigate the radioprotective effect of mercaptoethylamine on the thiol level of the outer cell membrane of the Ehrlich ascites tumor cells
  • modifier to investigate the polar microenvironment around the reactive Cys283 of rabbit muscle creatine kinase
  • dipyridyl-dithio substrate to evaluate the protein disulfide-thiol interchange activity of the auxin stimulated NADH: protein disulfide reductase (NADH oxidase) of soybean plasma membranes
  • water-soluble reagent in a study for introducing, in buffered saline, a reactive sulfhydryl group on water-soluble molecules bearing an alkyl-amino group
  • chromogen for sulfhydryl groups in the Ellman method for cholinesterase determinations
  • spectrophotometric determination of thiols and of total glutathione in human blood

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

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)

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P D Dass et al.
Veterinary and human toxicology, 39(1), 11-17 (1997-02-01)
A kinetic analysis of the substitution of 6,6'-dithiodinicotinic acid (DTNA) for 5,5'-dithiobis-2-nitrobenzoic acid (DTNB) for the determination of rat and human erythrocyte acetylcholinesterase (AChE; EC 3.1.1.7) and plasma butyrylcholinesterase (BuChE; EC 3.1.1.8) is presented. Increasing concentrations of DTNB, but not
J Nandi et al.
The Biochemical journal, 213(3), 587-594 (1983-09-01)
The distribution of free thiol groups associated with the membrane proteins of the purified pig gastric microsomal vesicles was quantified, and the relation of thiol groups to the function of the gastric (H+ + K+)-transporting ATPase system was investigated. Two
L Meunier et al.
Bioconjugate chemistry, 10(2), 206-212 (1999-03-17)
A simple method for introducing, in buffered saline, a reactive sulfhydryl group on water-soluble molecules bearing an alkyl-amino group is described. This method is based on the use of two water-soluble reagents: 2-iminothiolane and 6,6'-dithiodinicotinic acid. The first one is
The determination of thiols and of total glutathione in human blood using 6,6'-dithiodinicotinic acid (CPDS).
D R Grassetti et al.
Biochemical medicine, 12(2), 149-153 (1975-02-11)
[Quantitation of sulfhydryl groups on surface of erythrocytes].
X B Liu et al.
Zhongguo yi xue ke xue yuan xue bao. Acta Academiae Medicinae Sinicae, 8(2), 146-147 (1986-04-01)
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