4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid - 119-40-4

4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid

Catalog Number: EVT-520485
CAS Number: 119-40-4
Molecular Formula: C16H13NO4S
Molecular Weight: 315.3 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid, also known as Sudan I, is a synthetic organic compound that belongs to the azo dye family. It is commonly used as a coloring agent in various industries, including food, textiles, and plastics. However, it has been found to have potential health hazards, including carcinogenicity and genotoxicity.
Applications in Various Fields
In medical research, 4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I has been used as a model compound for studying the genotoxic and carcinogenic effects of azo dyes. It has also been investigated for its potential role in drug development, as it can bind to proteins and enzymes involved in disease pathways. In clinical trials, 4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I has not been used as a therapeutic agent due to its potential health hazards. In environmental research, 4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I has been found to have toxic effects on aquatic organisms and can accumulate in the food chain. It has also been used as a marker for pollution management, as it can be detected in wastewater and soil samples. In industrial research, 4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I has been used as a coloring agent in various products, but its use has been restricted due to its potential health hazards. It can also be used in manufacturing processes to improve product quality and efficiency, but health and safety considerations should be taken into account.

Properties

CAS Number

119-40-4

Product Name

4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid

IUPAC Name

7-anilino-4-hydroxynaphthalene-2-sulfonic acid

Molecular Formula

C16H13NO4S

Molecular Weight

315.3 g/mol

InChI

InChI=1S/C16H13NO4S/c18-16-10-14(22(19,20)21)9-11-8-13(6-7-15(11)16)17-12-4-2-1-3-5-12/h1-10,17-18H,(H,19,20,21)

InChI Key

YGNDWDUEMICDLW-UHFFFAOYSA-N

SMILES

C1=CC=C(C=C1)NC2=CC3=CC(=CC(=C3C=C2)O)S(=O)(=O)O

Canonical SMILES

C1=CC=C(C=C1)NC2=CC3=CC(=CC(=C3C=C2)O)S(=O)(=O)O
Method of Synthesis or Extraction
4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I can be synthesized by the diazotization of 4-amino-1-naphthol-3-sulfonic acid followed by coupling with aniline. The yield of this method is around 60-70%, and it requires the use of hazardous chemicals such as sodium nitrite and hydrochloric acid. Another method involves the reaction of 4-nitro-1-naphthol with aniline in the presence of sulfuric acid, followed by reduction with zinc dust. This method has a higher yield of around 80-90%, but it also involves the use of hazardous chemicals and generates toxic waste. Extraction of 4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I from commercial products can be done using organic solvents such as methanol or acetone, but this method is not efficient and may not yield pure 4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I. Environmental and safety considerations should be taken into account when using these methods, and proper disposal of hazardous waste should be ensured.
Chemical Structure and Biological Activity
4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I has a chemical formula of C16H12N2O3S and a molecular weight of 308.34 g/mol. It has a naphthalene backbone with a phenylamino group and a sulfonic acid group attached to it. 4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I has been found to have potential carcinogenic and genotoxic effects, as it can bind to DNA and cause mutations. It has also been shown to induce oxidative stress and inflammation in cells.
Biological Effects
4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I can affect cell function and signal transduction by inducing DNA damage and oxidative stress. It has been shown to activate the NF-κB pathway, which is involved in inflammation and cell survival. 4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I has also been found to inhibit the activity of topoisomerase II, an enzyme involved in DNA replication and repair. These effects can lead to potential therapeutic and toxic effects, depending on the dose and exposure.
Future Perspectives and Challenges
The use and study of 4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I face several limitations, including its potential health hazards, limited availability of pure samples, and lack of standardized methods for detection and analysis. Possible solutions and improvements include the development of safer and more efficient synthesis and extraction methods, the use of alternative coloring agents in industries, and the implementation of stricter regulations on the use of 4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I. Future trends and prospects in the application of 4-Hydroxy-7-(phenylamino)naphthalene-2-sulfonic acid I in scientific research include the investigation of its role in disease pathways and the development of safer and more effective therapeutic agents.

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