Naphthol AS-BI - 1237-75-8
Naphthol AS-BI
Catalog Number: BT-258683
CAS Number: 1237-75-8
Molecular Formula: C17H12BrNO3
Molecular Weight: 372.2 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Product Introduction
Description
Naphthol AS-BI is a synthetic dye that belongs to the class of azo dyes. It is widely used in various industries, including textile, paper, and leather, as a colorant. However, recent studies have shown that naphthol AS-BI possesses significant biological activity, making it a potential candidate for medical and environmental research.
Properties
CAS Number
1237-75-8
Product Name
Naphthol AS-BI
IUPAC Name
7-bromo-3-hydroxy-N-(2-hydroxyphenyl)naphthalene-2-carboxamide
Molecular Formula
C17H12BrNO3
Molecular Weight
372.2 g/mol
InChI
InChI=1S/C17H12BrNO3/c18-12-6-5-10-9-16(21)13(8-11(10)7-12)17(22)19-14-3-1-2-4-15(14)20/h1-9,20-21H,(H,19,22)
InChI Key
GGZWBSAHVQMQII-UHFFFAOYSA-N
SMILES
C1=CC=C(C(=C1)NC(=O)C2=C(C=C3C=CC(=CC3=C2)Br)O)O
Solubility
Soluble in DMSO
Synonyms
AI 3-50089; AI-3-50089; AI3-50089
Canonical SMILES
C1=CC=C(C(=C1)NC(=O)C2=C(C=C3C=CC(=CC3=C2)Br)O)O
Method of Synthesis or Extraction
Naphthol AS-BI can be synthesized by several methods, including diazotization and coupling reactions. The most commonly used method involves the diazotization of 2-naphthol with sodium nitrite in the presence of hydrochloric acid, followed by the coupling reaction with 4-aminobenzoic acid. The efficiency and yield of this method depend on the reaction conditions, such as temperature, pH, and concentration of reagents. The yield of naphthol AS-BI can range from 50% to 90%. However, the synthesis of naphthol AS-BI can also produce hazardous by-products, such as nitrous oxide, which can pose environmental and safety concerns.
Chemical Structure and Biological Activity
Naphthol AS-BI has a chemical structure consisting of a naphthalene ring and an azo group (-N=N-) linking to a benzene ring. The azo group is responsible for the coloration of the dye and also plays a crucial role in its biological activity. Naphthol AS-BI has been shown to exhibit antimicrobial, anti-inflammatory, and anticancer properties. The mechanism of action of naphthol AS-BI involves the inhibition of enzymes and signaling pathways involved in cell proliferation and inflammation.
Biological Effects
Naphthol AS-BI has been shown to affect cell function and signal transduction in various cell types. It can induce apoptosis (programmed cell death) in cancer cells and inhibit the growth of bacteria and fungi. However, naphthol AS-BI can also have potential toxic effects on cells and tissues, such as DNA damage and oxidative stress. Therefore, further studies are needed to determine the therapeutic and toxic effects of naphthol AS-BI.
Applications
In medical research, naphthol AS-BI has been investigated for its potential role in drug development. It has been shown to enhance the efficacy of certain anticancer drugs and reduce inflammation in animal models. Clinical trials are needed to determine the safety and efficacy of naphthol AS-BI in humans. In environmental research, naphthol AS-BI has been studied for its effects on ecosystems and its role in pollution management. It can be used as a biosorbent for the removal of heavy metals and dyes from wastewater. However, the use of naphthol AS-BI in the environment can also pose risks to aquatic organisms and human health. In industrial research, naphthol AS-BI is used in manufacturing processes to improve product quality and efficiency. Health and safety considerations are essential in the handling and disposal of naphthol AS-BI in industrial settings.
Future Perspectives and Challenges
The use and study of naphthol AS-BI face several limitations, such as its potential toxicity and environmental impact. Possible solutions and improvements include the development of safer and more efficient synthesis methods and the investigation of the structure-activity relationship of naphthol AS-BI. Future trends and prospects in the application of naphthol AS-BI in scientific research include the development of novel therapeutic agents and the exploration of its potential in nanotechnology and biotechnology.
Conclusion:
Naphthol AS-BI is a synthetic dye with significant biological activity, making it a potential candidate for medical and environmental research. Its synthesis, biological activity, and applications have been discussed in this paper. Further studies are needed to determine the therapeutic and toxic effects of naphthol AS-BI and to develop safer and more efficient synthesis methods.
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