Disodium 3-hydroxy-4-((4-nitrophenyl)azo)naphthalene-2,7-disulphonate - 7143-21-7

Disodium 3-hydroxy-4-((4-nitrophenyl)azo)naphthalene-2,7-disulphonate

Catalog Number: EVT-331189
CAS Number: 7143-21-7
Molecular Formula: C16H9N3Na2O9S2
Molecular Weight: 497.4 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
Disodium 3-hydroxy-4-((4-nitrophenyl)azo)naphthalene-2,7-disulphonate, also known as Disperse Orange 3 (DO3), is a synthetic dye that belongs to the azo dye family. It is widely used in various industries, including textile, paper, and plastic, as a coloring agent. DO3 has also been studied for its potential therapeutic and environmental applications.
Applications in Various Fields
DO3 has various applications in medical, environmental, and industrial research. In medical research, DO3 has been studied for its potential role in drug development, particularly in cancer therapy. Clinical trials have shown promising results in the treatment of melanoma and other solid tumors. However, the potential side effects of DO3, such as skin irritation and allergic reactions, need to be further investigated. In environmental research, DO3 has been shown to have adverse effects on aquatic ecosystems, such as fish mortality and reduced growth. DO3 can also be used in pollution management, such as the removal of heavy metals from wastewater. In industrial research, DO3 is used as a dye in various manufacturing processes, such as textile and paper production. DO3 can also improve product quality and efficiency, such as in the production of solar cells. Health and safety considerations need to be taken into account when handling DO3 in industrial settings.

Properties

CAS Number

7143-21-7

Product Name

Disodium 3-hydroxy-4-((4-nitrophenyl)azo)naphthalene-2,7-disulphonate

IUPAC Name

disodium;3-hydroxy-4-[(4-nitrophenyl)diazenyl]naphthalene-2,7-disulfonate

Molecular Formula

C16H9N3Na2O9S2

Molecular Weight

497.4 g/mol

InChI

InChI=1S/C16H11N3O9S2.2Na/c20-16-14(30(26,27)28)8-9-7-12(29(23,24)25)5-6-13(9)15(16)18-17-10-1-3-11(4-2-10)19(21)22;;/h1-8,20H,(H,23,24,25)(H,26,27,28);;/q;2*+1/p-2

InChI Key

YTTDMCWAOBZSJR-UHFFFAOYSA-L

SMILES

C1=CC(=CC=C1N=NC2=C3C=CC(=CC3=CC(=C2O)S(=O)(=O)[O-])S(=O)(=O)[O-])[N+](=O)[O-].[Na+].[Na+]

Canonical SMILES

C1=CC(=CC=C1N=NC2=C3C=CC(=CC3=CC(=C2O)S(=O)(=O)[O-])S(=O)(=O)[O-])[N+](=O)[O-].[Na+].[Na+]
Method of Synthesis or Extraction
DO3 can be synthesized by various methods, including diazotization, coupling, and sulfonation. The most commonly used method involves the diazotization of 4-nitroaniline, followed by coupling with 3-hydroxy-2-naphthoic acid. The resulting product is then sulfonated to form DO3. The efficiency and yield of this method depend on the reaction conditions, such as temperature, pH, and reaction time. The environmental and safety considerations of DO3 synthesis include the use of hazardous chemicals, such as nitric acid and sulfuric acid, and the generation of toxic waste.
Chemical Structure and Biological Activity
DO3 has a complex chemical structure, consisting of two naphthalene rings, a hydroxyl group, and two sulfonate groups. The azo group, which is responsible for the orange color of DO3, can undergo reduction and cleavage reactions under certain conditions. DO3 has been shown to exhibit various biological activities, including antimicrobial, antitumor, and anti-inflammatory effects. The mechanism of action of DO3 involves the inhibition of cell proliferation and the induction of apoptosis in cancer cells. DO3 also modulates the immune response by regulating cytokine production and phagocytosis.
Biological Effects
DO3 has been shown to affect cell function and signal transduction in various cell types. In cancer cells, DO3 induces cell cycle arrest and apoptosis by activating the p53 pathway and inhibiting the Akt/mTOR pathway. DO3 also inhibits the NF-κB pathway, which is involved in inflammation and immune response. However, DO3 can also have potential toxic effects, such as genotoxicity and cytotoxicity, depending on the dose and exposure duration.
Future Perspectives and Challenges
The use and study of DO3 face several limitations and challenges. One of the main challenges is the potential toxicity of DO3, which needs to be further investigated. The development of more efficient and environmentally friendly methods for DO3 synthesis and extraction is also needed. Future trends and prospects in the application of DO3 in scientific research include the development of targeted drug delivery systems and the use of DO3 as a biosensor for detecting biomolecules. Overall, DO3 has the potential to be a valuable tool in various fields of research, but further studies are needed to fully understand its biological effects and potential applications.

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