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Acid Brown 14

Catalog Number: BT-264571

CAS Number: 5850-16-8

Molecular Formula: C26H16N4Na2O8S2

Molecular Weight: 622.5 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Acid Brown 14 is a synthetic dye that belongs to the azo dye family. It is commonly used in the textile industry to dye cotton, wool, and silk. Acid Brown 14 has also been used in medical research as a potential drug candidate due to its biological activity. However, its use has been limited due to safety concerns and environmental impact. This paper will discuss the methods of synthesis or extraction, chemical structure, biological activity, biological effects, applications, future perspectives, and challenges of Acid Brown 14.

Properties

CAS Number

5850-16-8

Product Name

Acid Brown 14

IUPAC Name

disodium;4-[2-[4,6-dioxo-5-[(4-sulfonatonaphthalen-1-yl)hydrazinylidene]cyclohex-2-en-1-ylidene]hydrazinyl]naphthalene-1-sulfonate

Molecular Formula

C26H16N4Na2O8S2

Molecular Weight

622.5 g/mol

InChI

InChI=1S/C26H18N4O8S2.2Na/c31-22-12-9-21(29-27-19-10-13-23(39(33,34)35)17-7-3-1-5-15(17)19)26(32)25(22)30-28-20-11-14-24(40(36,37)38)18-8-4-2-6-16(18)20;;/h1-14,27-28H,(H,33,34,35)(H,36,37,38);;/q;2*+1/p-2

InChI Key

NMZNGCLVMMUXIC-ZQGAZYNISA-L

SMILES

C1=CC=C2C(=C1)C(=CC=C2S(=O)(=O)[O-])NN=C3C=CC(=O)C(=NNC4=CC=C(C5=CC=CC=C54)S(=O)(=O)[O-])C3=O.[Na+].[Na+]

Solubility

Soluble in DMSO

Synonyms

C.I. 20195; NSC 75909; NSC-75909; NSC75909

Canonical SMILES

C1=CC=C2C(=C1)C(=CC=C2S(=O)(=O)[O-])NN=C3C=CC(=O)C(=NNC4=CC=C(C5=CC=CC=C54)S(=O)(=O)[O-])C3=O.[Na+].[Na+]

Isomeric SMILES

C1=CC=C2C(=C1)C(=CC=C2S(=O)(=O)[O-])N/N=C\3/C=CC(=O)/C(=N/NC4=CC=C(C5=CC=CC=C54)S(=O)(=O)[O-])/C3=O.[Na+].[Na+]

Method of Synthesis or Extraction

Acid Brown 14 can be synthesized by the diazotization of 4-aminoazobenzene followed by coupling with 2-naphthol-3,6-disulfonic acid. The yield of this method is around 70%, and it is considered efficient. However, the synthesis of Acid Brown 14 involves the use of toxic chemicals such as nitrous acid, which can be hazardous to the environment and human health. Therefore, alternative methods such as enzymatic synthesis and electrochemical synthesis have been explored. Enzymatic synthesis has shown promising results with high yields and minimal environmental impact.

Chemical Structure and Biological Activity

The chemical structure of Acid Brown 14 consists of an azo group (-N=N-) and two sulfonic acid groups (-SO3H). The azo group is responsible for its color, while the sulfonic acid groups make it water-soluble. Acid Brown 14 has been shown to have biological activity, particularly in inhibiting the growth of cancer cells. It works by inhibiting the activity of topoisomerase II, an enzyme that is essential for DNA replication. Acid Brown 14 has also been shown to have antimicrobial activity against various bacteria and fungi.

Biological Effects

Acid Brown 14 has been shown to have potential therapeutic effects in medical research. It has been studied as a potential drug candidate for the treatment of cancer, but its use has been limited due to safety concerns. Acid Brown 14 has been shown to have toxic effects on cells, particularly in high concentrations. It can cause DNA damage and induce apoptosis, or programmed cell death. Acid Brown 14 has also been shown to have potential toxic effects on the environment, particularly in aquatic ecosystems. It can cause harm to aquatic organisms and disrupt the balance of the ecosystem.

Applications

In medical research, Acid Brown 14 has been studied as a potential drug candidate for the treatment of cancer. It has shown promising results in inhibiting the growth of cancer cells, but its use has been limited due to safety concerns. Acid Brown 14 has also been studied for its potential use in the treatment of bacterial and fungal infections. In environmental research, Acid Brown 14 has been studied for its effects on aquatic ecosystems. It has been shown to have potential harmful effects on aquatic organisms and disrupt the balance of the ecosystem. In industrial research, Acid Brown 14 has been used in the textile industry to dye cotton, wool, and silk. It has also been used in the manufacturing of paper and leather.

Future Perspectives and Challenges

The use of Acid Brown 14 in medical research has been limited due to safety concerns. Future research should focus on developing safer and more effective alternatives. The use of enzymatic synthesis and electrochemical synthesis should be explored further to reduce the environmental impact of Acid Brown 14. In environmental research, more studies should be conducted to understand the potential harmful effects of Acid Brown 14 on aquatic ecosystems. In industrial research, efforts should be made to reduce the use of Acid Brown 14 and develop safer alternatives.
Conclusion
Acid Brown 14 is a synthetic dye that has been used in the textile industry and studied for its potential use in medical research. It has shown promising results in inhibiting the growth of cancer cells and has antimicrobial activity against various bacteria and fungi. However, its use has been limited due to safety concerns and environmental impact. Future research should focus on developing safer and more effective alternatives and reducing the environmental impact of Acid Brown 14.

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