71899-86-0

Basic information

• Product Name: 5-(2-AMINOETHYL)DITHIO-2-NITROBENZOIC ACID
• Synonyms: 5-(2-AMINOETHYL)DITHIO-2-NITROBENZOIC ACID
• CAS NO: 71899-86-0
• Molecular Formula: C₉H₁₀N₂O₄S₂
• Molecular Weight: 274.32
• Product Categories: Amines;Aromatics;Sulfur & Selenium Compounds;MTS and Sulfhydryl Active Reagents;MTS & Sulfhydryl Active Reagents
• Mol File: 71899-86-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Solubility: Water
• CAS DataBase Reference: 5-(2-AMINOETHYL)DITHIO-2-NITROBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-AMINOETHYL)DITHIO-2-NITROBENZOIC ACID(71899-86-0)
• EPA Substance Registry System: 5-(2-AMINOETHYL)DITHIO-2-NITROBENZOIC ACID(71899-86-0)

Safety Data

• Hazardous Substances Data: 71899-86-0(Hazardous Substances Data)

Usage

Description

5-(2-AMINOETHYL)DITHIO-2-NITROBENZOIC ACID is an organic compound characterized by its pale yellow solid appearance. It is known for its improved stability under alkaline conditions, making it a suitable alternative to Ellman's reagent in various applications.

Uses

Used in Chemical Analysis:
5-(2-AMINOETHYL)DITHIO-2-NITROBENZOIC ACID is used as a quantification agent for the measurement of thiol contents. It is particularly effective in enzymatic assays conducted under basic pH conditions due to its enhanced stability in alkaline environments.
Used in Research and Development:
In the field of research and development, 5-(2-AMINOETHYL)DITHIO-2-NITROBENZOIC ACID serves as a valuable alternative to Ellman's reagent. It is utilized for its ability to react with free thiols, providing a more stable and reliable option for experiments and assays.
Used in Pharmaceutical Industry:
5-(2-AMINOETHYL)DITHIO-2-NITROBENZOIC ACID is employed in the pharmaceutical industry as a base-stable alternative to Ellman's reagent. Its improved stability under alkaline conditions makes it an excellent choice for drug development and testing processes that require accurate quantification of thiol contents.
Used in Environmental Science:
In environmental science, 5-(2-AMINOETHYL)DITHIO-2-NITROBENZOIC ACID is used for the assessment of thiol content in various samples, such as soil, water, and air. Its stability under basic pH conditions allows for more accurate and reliable measurements in environmental monitoring and assessment.
Used in Material Science:
5-(2-AMINOETHYL)DITHIO-2-NITROBENZOIC ACID is utilized in material science for the development of new materials with enhanced properties. Its ability to react with free thiols and its stability under alkaline conditions make it a valuable component in the creation of advanced materials with specific characteristics and applications.

Upstream product

• 69-78-3 5,5'-dithiobis-(2-nitrobenzoic acid) 
• 60-23-1 Cysteamine 
• 156-57-0 2-mercaptoethylamine hydrochloride 

Downstream Products

• 22801-37-2 3-(2-amino-ethyldisulfanyl)-L-alanine 
• 15139-21-6 5-thio-2-nitrobenzoic acid 
• 13244-81-0 (S)-2-Amino-4-[(R)-2-(2-amino-ethyldisulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid 
• 51-85-4 2,2'-dithio-bis[ethylamine] 
• 638-43-7 S-carboxymethylthiocysteamine 
• 15579-01-8 2-[(2-aminoethyl)disulfanyl]ethan-1-ol 
• 15579-00-7 3-<(2-aminoethyl)dithio>propionic acid 
• 77874-90-9 3-carboxylato-4-nitrothiophenoxide ion 

Relevant articles and documents

5-(2-Aminoethyl)dithio-2-nitrobenzoate as a more base-stable alternative to ellman's reagent

(Chemical Equation Presented) 5-(2-Aminoethyl)dithio-2-nitrobenzoate (ADNB) reacts with free thiols with kinetics similar to those of Ellman's reagent but has dramatically improved stability under alkaline conditions, making it an excellent alternative to Ellman's reagent for the quantitation of thiol contents and enzymatic assays under basic pH conditions.

A kinetic approach to characterize the electrostatic environments of thiol groups in proteins

In this study, we synthesized a zwitterionic DTNB derivative, 5-(2- aminoethyl)-dithio-2-nitrobenzoate (ADNB), and characterized its reactions with several cationic, anionic, and neutral thiols. Reactions with ADNB, unlike those with DTNB, are relatively insensitive to electrostatic environments and ionic strengths. At relatively low ionic strength, rate ratios, k(ADNB)/k(DTNB), varied from 0.22 for reactions with low-molecular- weight cationic thiols to 3.0 for those with low-molecular-weight anionic thiols. A k(ADNB)/k(DTNB) ratio of ~200 for Cys-34 of BSA appears to reflect a very anionic environment. k(ADNB)/k(DTNB) ratios of ~6 and ~1, respectively, for canine and equine serum albumins, which have Glu-82 → Asp and Glu-82 → Ala substitutions suggest Glu-82 is the most important anionic residues affecting the reactivity of Cys-34 in BSA. k(ADNB)/k(DTNB) ratios appear to be useful for characterizing electrostatic environments of thiol groups in proteins.

A KINETIC STUDY OF THE THIOL-DISULFIDE EXCHANGE REACTION BETWEEN AMINOTHIOLS AND 5,5'-DITHIOBIS(2-NITROBENZOIC ACID)

The rate constants for the thiol-disulfide exchange, kSH, and for the thiolate ion-disulfide exchange, ks-, between biologically relevant aminothiols, i.e., cysteine, cysteamine and penicillamine, and 5,5'-dithiobis(2-nitrobenzoic acid), Ellman's reagent, in aqueous solutions were determined by a spectrophotometric method.The apparent rate constant, k1', increases with increase of pH under the experimental conditions used.The value of ks-, approximately 2x1E5 M-1s-1 except for penicillamine, appears to be independent of the pKa (SH), and kSH is three orders of magnitude smaller than ks-.The thiolate ion-disulfide exchange in penicillamine is one order of magnitude slower than in the other aminothiols.The results of the kinetic study indicate that one of the sulfur atoms of disulfide is attacked by the thiolate anion with subsequent cleavage of the S-S bond.Keywords: Ellman's reagent; thiol-disulfide exchange; rate constant; cysteine; cysteamine; penicillamine; aminothiol