4-amino-3-hydroxy Benzoic Acid

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Exploring 4-Amino-3-HydroxyBenzoic Acid (CAS No: 2374-03-0): A Key Compound in Chemistry and Medicine
In the realm of organic chemistry, compounds with a unique combination of functional groups can exhibit remarkable properties. One such compound is 4-Amino-3-HydroxyBenzoic Acid, identified by its Chemical Abstracts Service (CAS) number 2374-03-0. This compound plays a significant role in various scientific and industrial applications, ranging from the development of pharmaceutical agents to its potential use in research and manufacturing.

What is 4-Amino-3-HydroxyBenzoic Acid?
4-Amino-3-Hydroxy Benzoic Acid is an organic compound that belongs to the family of benzoic acids. Its structure consists of a benzene ring, with two key substituents:
Amino group (-NH2) attached at the 4-position.
Hydroxyl group (-OH) attached at the 3-position.
This arrangement makes it a derivative of salicylic acid, which is the base compound for many aspirin-like drugs. However, the introduction of the amino group opens up new avenues for chemical reactions and biological interactions.
Chemical Structure ...
... and Properties
The IUPAC name for 4-Amino-3-HydroxyBenzoic Acid is 3-hydroxy-4-aminobenzoic acid, reflecting the locations of the functional groups on the benzene ring. With the molecular formula C7H7NO3, the compound is a white to off-white solid, typically in crystalline form. The key physical properties include:
Molecular weight: 167.14 g/mol
Melting point: Around 180–185°C
Solubility: It is sparingly soluble in water but soluble in organic solvents such as ethanol and methanol.
The hydroxyl group (–OH) and the amino group (–NH2) contribute to its potential reactivity, allowing it to be involved in diverse reactions such as esterification, nucleophilic substitution, and condensation.
Applications in Pharmaceutical and Medicinal Chemistry
4-Amino-3-Hydroxy Benzoic Acid is primarily known for its role in the development of drugs and pharmaceuticals. Its structural similarity to salicylic acid (the active ingredient in aspirin) makes it a valuable starting point for the synthesis of compounds with anti-inflammatory and analgesic properties. By modifying its structure, researchers can create derivatives with enhanced biological activity.
One of the most notable applications of 4-Amino-3-Hydroxy Benzoic Acid is its involvement in the synthesis of para-aminosalicylic acid (PAS). PAS has been historically used as an anti-tuberculosis drug, especially in the era before more modern antibiotics were developed. The compound is effective in combating the tuberculosis-causing bacteria Mycobacterium tuberculosis, and its derivatives continue to be studied for their potential in treating resistant strains.
In addition to its use in tuberculosis treatments, 4-Amino-3-Hydroxy Benzoic Acid is a key intermediate in the manufacture of azo dyes. These dyes are widely used in the textile industry and also find applications in biological staining techniques.
Research and Analytical Uses
Due to its structural characteristics, 4-Amino-3-Hydroxy Benzoic Acid is also useful in research settings. In particular, it is used as a pH indicator, as the pKa values of the amino and hydroxyl groups make it sensitive to changes in pH. Additionally, its chemical properties make it an ideal candidate for studying the interaction between organic compounds and biological systems.
Scientists and chemists have studied 4-Amino-3-HydroxyBenzoic Acid in relation to its ability to form complexes with metal ions. This property is valuable in fields such as coordination chemistry and environmental science, where it is used in the detection and removal of heavy metals from solutions.
Environmental Impact and Safety
As with many chemicals, it is essential to consider the environmental and safety implications of using 4-Amino-3-HydroxyBenzoic Acid. The compound is not typically regarded as highly toxic, but as with most chemical reagents, it should be handled with care. It is advisable to avoid inhalation or direct contact with the skin or eyes, as it can cause irritation. Moreover, as with many synthetic chemicals, appropriate disposal methods should be followed to prevent contamination of soil and water resources.
Conclusion
4-Amino-3-HydroxyBenzoic Acid (CAS No: 2374-03-0) is a fascinating compound with diverse applications in both medicinal chemistry and industrial processes. Whether in the development of anti-tuberculosis drugs, the creation of azo dyes, or its utility as a pH indicator in laboratory research, its unique structure and reactivity continue to make it an important compound in the world of chemistry.
For researchers, chemists, and pharmaceutical developers, understanding the properties and uses of compounds like 4-Amino-3-HydroxyBenzoic Acid can lead to innovations in medicine and industry, while also offering new pathways for scientific discovery.
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