1,4-Naphthalenedicarboxylic acid - 605-70-9

1,4-Naphthalenedicarboxylic acid

Catalog Number: EVT-304276
CAS Number: 605-70-9
Molecular Formula: C12H8O4
Molecular Weight: 216.19 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
1,4-Naphthalenedicarboxylic acid (NDA) is a dicarboxylic acid with a naphthalene backbone. It is a white crystalline powder that is soluble in water and organic solvents. NDA has been widely used in various fields, including medical, environmental, and industrial research.
Applications in Various Fields
1,4-Naphthalenedicarboxylic acid has been used in various fields, including medical, environmental, and industrial research. In medical research, 1,4-Naphthalenedicarboxylic acid has been investigated for its potential role in drug development. For example, 1,4-Naphthalenedicarboxylic acid derivatives have been synthesized and tested for their anti-inflammatory and antitumor activities. Clinical trials are needed to evaluate the safety and efficacy of 1,4-Naphthalenedicarboxylic acid-based drugs in humans.
In environmental research, 1,4-Naphthalenedicarboxylic acid has been studied for its effects on ecosystems and its role in pollution management. For example, 1,4-Naphthalenedicarboxylic acid has been shown to adsorb heavy metals and organic pollutants from water and soil. 1,4-Naphthalenedicarboxylic acid-based materials have also been developed for wastewater treatment and environmental remediation.
In industrial research, 1,4-Naphthalenedicarboxylic acid has been used in manufacturing processes to improve product quality and efficiency. For example, 1,4-Naphthalenedicarboxylic acid has been used as a monomer in the synthesis of polyimides, which have high thermal stability and mechanical strength. Health and safety considerations should be taken into account when using 1,4-Naphthalenedicarboxylic acid in industrial applications.

Properties

CAS Number

605-70-9

Product Name

1,4-Naphthalenedicarboxylic acid

IUPAC Name

naphthalene-1,4-dicarboxylic acid

Molecular Formula

C12H8O4

Molecular Weight

216.19 g/mol

InChI

InChI=1S/C12H8O4/c13-11(14)9-5-6-10(12(15)16)8-4-2-1-3-7(8)9/h1-6H,(H,13,14)(H,15,16)

InChI Key

ABMFBCRYHDZLRD-UHFFFAOYSA-N

SMILES

C1=CC=C2C(=C1)C(=CC=C2C(=O)O)C(=O)O

Canonical SMILES

C1=CC=C2C(=C1)C(=CC=C2C(=O)O)C(=O)O
Method of Synthesis or Extraction
1,4-Naphthalenedicarboxylic acid can be synthesized by several methods, including oxidation of naphthalene, Friedel-Crafts acylation of naphthalene, and hydrolysis of naphthalene-1,4-dicarboxylic acid diethyl ester. The efficiency and yield of each method vary depending on the reaction conditions. For example, the oxidation of naphthalene using potassium permanganate as an oxidizing agent can yield up to 80% of 1,4-Naphthalenedicarboxylic acid. However, this method requires a high temperature and long reaction time, which may result in low selectivity and yield. The Friedel-Crafts acylation of naphthalene using acetic anhydride and aluminum chloride as catalysts can yield up to 90% of 1,4-Naphthalenedicarboxylic acid. This method is relatively simple and efficient, but it may produce toxic byproducts and require careful handling. The hydrolysis of naphthalene-1,4-dicarboxylic acid diethyl ester using sodium hydroxide can yield up to 95% of 1,4-Naphthalenedicarboxylic acid. This method is mild and selective, but it may require a long reaction time and produce a large amount of waste.
Environmental and safety considerations should be taken into account when synthesizing 1,4-Naphthalenedicarboxylic acid. The use of toxic or hazardous reagents and solvents should be minimized or avoided. The waste generated during the synthesis should be properly treated and disposed of to prevent environmental pollution.
Chemical Structure and Biological Activity
1,4-Naphthalenedicarboxylic acid has a planar structure with two carboxylic acid groups attached to the naphthalene ring. It can form hydrogen bonds and π-π interactions with other molecules, which may affect its biological activity. 1,4-Naphthalenedicarboxylic acid has been shown to exhibit various biological activities, including anti-inflammatory, antioxidant, antitumor, and antimicrobial effects.
The mechanism of action and biological targets of 1,4-Naphthalenedicarboxylic acid are not fully understood. However, it has been suggested that 1,4-Naphthalenedicarboxylic acid may modulate cell function and signal transduction pathways by interacting with specific receptors or enzymes. For example, 1,4-Naphthalenedicarboxylic acid has been shown to inhibit the activity of cyclooxygenase-2 (COX-2), an enzyme involved in the production of inflammatory mediators. 1,4-Naphthalenedicarboxylic acid has also been shown to activate the nuclear factor erythroid 2-related factor 2 (Nrf2) pathway, which plays a role in antioxidant defense and cell survival.
The bioactivity and potency of 1,4-Naphthalenedicarboxylic acid may vary depending on the chemical structure, concentration, and mode of administration. Further studies are needed to elucidate the pharmacological properties of 1,4-Naphthalenedicarboxylic acid and its potential therapeutic applications.
Biological Effects
1,4-Naphthalenedicarboxylic acid may have both therapeutic and toxic effects on cells and organisms. The potential therapeutic effects of 1,4-Naphthalenedicarboxylic acid include anti-inflammatory, antioxidant, antitumor, and antimicrobial activities. For example, 1,4-Naphthalenedicarboxylic acid has been shown to reduce the production of pro-inflammatory cytokines and reactive oxygen species in vitro and in vivo. 1,4-Naphthalenedicarboxylic acid has also been shown to inhibit the growth and metastasis of cancer cells in animal models.
However, 1,4-Naphthalenedicarboxylic acid may also have toxic effects on cells and organisms. For example, 1,4-Naphthalenedicarboxylic acid has been shown to induce oxidative stress and DNA damage in vitro and in vivo. 1,4-Naphthalenedicarboxylic acid has also been shown to cause cytotoxicity and apoptosis in certain cell types. The toxic effects of 1,4-Naphthalenedicarboxylic acid may depend on the concentration, exposure time, and cell type.
Future Perspectives and Challenges
The use and study of 1,4-Naphthalenedicarboxylic acid face several limitations and challenges. For example, the synthesis of 1,4-Naphthalenedicarboxylic acid may require toxic or hazardous reagents and solvents, which may pose environmental and safety risks. The biological activity and mechanism of action of 1,4-Naphthalenedicarboxylic acid are not fully understood, which may limit its therapeutic potential. The toxicity and side effects of 1,4-Naphthalenedicarboxylic acid-based drugs need to be carefully evaluated in preclinical and clinical studies.
Possible solutions and improvements include the development of more efficient and selective synthesis methods, the identification of specific biological targets and mechanisms of action, and the evaluation of the safety and efficacy of 1,4-Naphthalenedicarboxylic acid-based drugs in humans. Future trends and prospects in the application of 1,4-Naphthalenedicarboxylic acid in scientific research may include the development of novel 1,4-Naphthalenedicarboxylic acid derivatives with improved pharmacological properties and the integration of 1,4-Naphthalenedicarboxylic acid-based materials in sustainable technologies.
In conclusion, 1,4-Naphthalenedicarboxylic acid is a versatile compound with potential applications in various fields. The synthesis, biological activity, and applications of 1,4-Naphthalenedicarboxylic acid have been discussed in this paper. Further studies are needed to fully understand the properties and potential of 1,4-Naphthalenedicarboxylic acid and its derivatives.

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