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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.)

functional group

carboxylic acid
disulfide

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

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
0000237940
0000205666
0000164890
0000210532
MKBM7197V

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The interaction of 6,6'-dithiodinicotinic acid with thiols and with ehrlich ascites tumor cells.
D R Grassetti et al.
Biochemical pharmacology, 18(3), 603-611 (1969-03-01)
J Nishiyama et al.
Analytical biochemistry, 138(1), 95-98 (1984-04-01)
A simple and rapid method for the determination of nanomole levels of biological thiols is described. The analysis is based on the combination of reverse-phase high-performance liquid chromatography with a postcolumn reaction with 6,6'-dithiodinicotinic acid. Thiols, including cysteine, cysteamine, thiolhistidine
Labeling of thiols involved in the activity of complex V of the mitochondrial oxidative phosphorylation system.
C Godinot et al.
The Journal of biological chemistry, 256(13), 6776-6782 (1981-07-10)
Timo Wille et al.
Toxicology mechanisms and methods, 21(7), 533-537 (2011-04-08)
For the diagnosis and therapy monitoring of intoxications with organophosphorus compounds, the determination of acetylcholinesterase (AChE) activity in whole blood is crucial. Usually, this testing is done with the colorimetric Ellman test using 412 nm wavelength and 5,5'-dithiobis-nitrobenzoic acid (DTNB) as
D J Morré et al.
Molecular and cellular biochemistry, 200(1-2), 7-13 (1999-11-24)
Dipyridyl-dithio substrates were cleaved by isolated vesicles of plasma membranes prepared from etiolated hypocotyls of soybean. The cleavage was stimulated by auxins at physiological concentrations. The substrates utilized were principally 2,2'-dithiodipyridine (DTP) and 6,6'-dithiodinicotinic acid (DTNA). The DTP generated 2
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