2435-59-8

Basic information

• Product Name: 5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone
• Synonyms: 5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone;5-Amino-3-(5-amino-1,2,3,6-tetrahydro-2,6-dioxopyridin-3-ylidene)-2,6(1H,3H)-pyridinedione;Indigoidin
• CAS NO: 2435-59-8
• Molecular Formula: C₁₀H₈N₄O₄
• Molecular Weight: 248.19492
• Mol File: 2435-59-8.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 285.6°Cat760mmHg
• Flash Point: 126.6°C
• Appearance: /
• Density: 1.637g/cm³
• PKA: 5.88±0.40(Predicted)
• CAS DataBase Reference: 5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone(2435-59-8)
• EPA Substance Registry System: 5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone(2435-59-8)

Safety Data

• Hazardous Substances Data: 2435-59-8(Hazardous Substances Data)

Usage

Description

5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone is an organic compound characterized by its unique molecular structure, featuring a bipyridine core with a Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'-tetraone moiety. 5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone is known for its potential applications in various fields due to its chemical properties and reactivity.

Uses

Used in Chemical Synthesis:
5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone is used as a building block for the synthesis of complex organic molecules and pharmaceutical compounds. Its unique structure allows for the formation of various derivatives with different functional groups, making it a versatile starting material in organic chemistry.
Used in Analytical Chemistry:
As a chelating agent, 5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone can be employed in analytical chemistry for the selective detection and quantification of metal ions. Its ability to form stable complexes with certain metals makes it a valuable tool in this field.
Used in Environmental Applications:
5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone can be utilized in environmental applications, such as the removal of heavy metal contaminants from water and soil. Its chelating properties enable it to bind and sequester metal ions, facilitating their removal from the environment.
Used in Pharmaceutical Industry:
5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone is used as an active pharmaceutical ingredient or as an intermediate in the synthesis of various drugs. Its unique chemical properties make it a promising candidate for the development of new therapeutic agents.
Used in Dye and Pigment Industry:
5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone can be employed as a natural dye or pigment in the textile, leather, and paper industries. Its bright and sustainable color, along with its potential health benefits as an antioxidant and antimicrobial agent, make it a promising alternative to synthetic dyes.
Used in Cosmetics Industry:
In the cosmetics industry, 5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone can be used as a colorant for various products, such as hair dyes, makeup, and skincare products. Its natural origin and potential health benefits make it an attractive option for cosmetic formulations.
Used in Food and Beverage Industry:
5,5'-Diamino-Δ3,3'(2H,2'H)-bipyridine-2,2',6,6'(1H,1'H)-tetraone can be utilized as a natural colorant in the food and beverage industry, providing a bright and sustainable blue color to products such as cereals, baked goods, and ice cream. Its safety for use in the food and drinks, as demonstrated by a patented purification process, makes it a viable option for this application.

Biosynthesis

Indigoidine is a water-insoluble blue pigment that was first isolated from phytopathogenic Erwinia as a powerful radical scavenger that enables phytopathogens to tolerate oxidative stress, organic peroxides, and superoxides during the plant defense response due to its structure of carbon–carbon double bonds conjugated with a carbonyl group. This bacterial pigment shows a bright blue color similar to that of indigo. Several different strains are reported to produce it. Indigoidine is assembled from two units of L-glutamine by a nonribosomal peptide synthetase (e.g. IndC from Erwinia chrysanthemi and Streptomyces aureofaciens CCM 3239, BpsA from Streptomyces lavendulae and Sc-indC from Streptomyces chromofuscus ATCC 49982) (Figure 1.7b). Recently, an indigoidine biosynthetic gene cluster was located in the genome of S. chromofuscus ATCC 49982. The gene cluster is silent and consists of five open reading frames, called orf1, Sc-indC, Sc-indA, Sc-indB, and orf2. Sc-IndC was functionally characterized as an indigoidine synthase through heterologous expression of the enzyme in both Streptomyces coelicolor CH999 and E. coli BAP1. The titer of indigoidine in E. coli BAP1 was reported to be 2.78 g/L under optimized conditions. Its production was dramatically increased (by 41.4%/3.93 g/L) when Sc-IndB was co-expressed with it in E. coli BAP1 (Yu et al. 2013). In order to further improve production, a glutamine synthetase gene was amplified from E. coli and co-expressed with Sc-indC and Sc-indB in E. coli BAP1. At 2.5 mM (NH4)2HPO4, the titer can reach 7.08±0.11 g/L (Xu et al. 2015). This provides a green, efficient production process for this promising blue dye.

Downstream Products

• 75771-90-3 3-n-octanamidopyridine-2,5,6-trione, N-benzyl derivative