646-08-2

Basic information

• Product Name: N,N'-(dithiodiethylene)bis[3-aminopropionamide]
• Synonyms: N,N'-(dithiodiethylene)bis[3-aminopropionamide];alethine
• CAS NO: 646-08-2
• Molecular Formula: C₁₀H₂₂N₄O₂S₂
• Molecular Weight: 294.43728
• EINECS: 211-465-6
• Mol File: 646-08-2.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,N'-(dithiodiethylene)bis[3-aminopropionamide](CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-(dithiodiethylene)bis[3-aminopropionamide](646-08-2)
• EPA Substance Registry System: N,N'-(dithiodiethylene)bis[3-aminopropionamide](646-08-2)

Safety Data

• Hazardous Substances Data: 646-08-2(Hazardous Substances Data)

Usage

General Description

N,N'-(dithiodiethylene)bis[3-aminopropionamide], also known as DETADA, is a chemical compound commonly used as a cross-linking agent in the production of rubber and other polymeric materials. It is a versatile compound that has strong adhesive properties and is often used in industrial adhesives, sealants, and coatings. DETADA also exhibits antioxidant properties, making it a valuable component in the production of materials that require protection from oxidative degradation. Additionally, it is used in biomedical research as a cross-linking agent for biomolecules and in the development of drug delivery systems. However, it is important to handle DETADA with caution due to its potential to cause skin and eye irritation, as well as its harmful effects if ingested or inhaled.

Upstream product

• 539-83-3 β-alanine-(2-mercapto-ethylamide) 
• 87503-54-6 bis-{2-[(N,N-phthaloyl-β-alanyl)-amino]-ethyl}-disulfide 
• 1801-55-4 2-(4,5-dihydro-thiazol-2-yl)-ethylamine 
• 5652-99-3 N-benzyloxycarbonyl-β-alanine-(2-benzylsulfanyl-ethylamide) 
• 104071-84-3 bis-{2-[(N-benzyloxycarbonyl-β-alanyl)-amino]-ethyl}-disulfide 
• 14348-31-3 3-Chloro-N-{2-[2-(3-chloro-propionylamino)-ethyldisulfanyl]-ethyl}-propionamide 

Downstream Products

• 138148-35-3 D-pantethine 

Relevant articles and documents

Investigating the role of the geminal dimethyl groups of coenzyme A: Synthesis and studies of a didemethyl analogue

An analogue 2 of coenzyme A (CoA) has been prepared in which the geminal methyl groups are replaced with hydrogens. An NMR titration study was conducted and shifts in frequency of protons in the pantetheine portion of the molecule upon titration of the adenine base were observed as has been previously reported with CoA. These studies indicate that the geminal dimethyl groups are not essential for adoption of a partially folded conformation in solution. Based on 1H-1H coupling constants, the distribution of conformations about the carbon-carbon bonds in the region of the methyl deletion were estimated. The results suggest that the conformer distribution is similar to that of CoA, but with small increases in population of the anti conformers. A simple model compound containing the didemethyl pantoamide moiety was prepared and subjected to similar conformational analysis. The coupling constants and predicted conformer distribution were almost identical to that of the CoA analogue, indicating that the conformer distribution is controlled by local interactions and not influenced by interactions between distant parts of the CoA molecule. The acetyl derivative of 2 was a fairly good substrate for the acetyl-CoA utilizing enzymes carnitine acetyltransferase, chloramphenicol acetyltransferase, and citrate synthase, with 1.3- to 10-fold increased K(m) values and 2.5- to 11-fold decreases in V(max). The combined results indicate that the geminal dimethyl groups of CoA have modest effects on function and minimal effects on conformation. Copyright (C) 2000 Elsevier Science Ltd.