5-Hydroxyanthranilic acid
[CAS# 394-31-0]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other amino acid derivatives
• Name: 5-Hydroxyanthranilic acid
• Synonyms: 2-Amino-5-hydroxybenzoic acid
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.14
• CAS Registry Number: 394-31-0
• EC Number: 628-812-6
• SMILES: C1=CC(=C(C=C1O)C(=O)O)N

Properties

• Melting point: 233-234 °C
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

5-Hydroxyanthranilic acid is an organic compound first identified in the early 20th century during investigations into the metabolic pathways of tryptophan. This compound is a hydroxylated derivative of anthranilic acid and plays a significant role as an intermediate in the kynurenine pathway, a major route of tryptophan catabolism. The discovery of 5-Hydroxyanthranilic acid highlighted its importance in various biological processes and spurred further research into its physiological and pathological roles.

5-Hydroxyanthranilic acid is pivotal in biomedical research due to its involvement in the kynurenine pathway. This pathway is crucial in understanding the metabolism of tryptophan and its implications for human health. Abnormalities in the kynurenine pathway are associated with several diseases, including neurodegenerative disorders like Alzheimer's and Parkinson's diseases, as well as psychiatric conditions such as depression and schizophrenia. Studying 5-Hydroxyanthranilic acid helps researchers elucidate these links, paving the way for new therapeutic strategies.

In the pharmaceutical industry, 5-Hydroxyanthranilic acid serves as a potential target for drug development. Compounds that modulate the kynurenine pathway, including 5-Hydroxyanthranilic acid, are being explored for their therapeutic effects. For instance, inhibitors of enzymes that interact with 5-Hydroxyanthranilic acid could help manage conditions linked to excessive neuroinflammation and oxidative stress. By targeting specific steps in the pathway, new treatments for inflammatory diseases, neurodegenerative disorders, and certain cancers can be developed.

5-Hydroxyanthranilic acid also finds relevance in nutritional science. Understanding its role in tryptophan metabolism aids in devising dietary strategies to optimize health. Tryptophan is an essential amino acid found in many protein-rich foods, and its metabolism through the kynurenine pathway impacts various physiological functions, including immune response and neurological health. Nutritional interventions that influence the levels of 5-Hydroxyanthranilic acid might contribute to improved health outcomes, particularly in managing conditions like chronic inflammation and mental health disorders.

In environmental science, 5-Hydroxyanthranilic acid can be studied as a bioindicator of soil and water health due to its presence in microbial metabolic processes. Additionally, in agriculture, understanding the metabolism of tryptophan and its derivatives in plants can aid in developing crops with enhanced resistance to stress and diseases. By leveraging the pathways involving 5-Hydroxyanthranilic acid, agricultural practices can be improved to yield more resilient and nutritious crops.

References

2021. Computational investigations, Hirshfeld surface analysis, interaction energy calculations, and energy framework crystal structure of methyl 2-amino-5-hydroxybenzoate. Journal of Structural Chemistry.
DOI: 10.1134/s0022476621110111

2013. Mutasynthesis of pyrrole spiroketal compound using calcimycin 3-hydroxy anthranilic acid biosynthetic mutant. Applied Microbiology and Biotechnology.
DOI: 10.1007/s00253-013-4882-1

2011. The Involvement of Neuroinflammation and Kynurenine Pathway in Parkinson's Disease. Parkinson's Disease.
DOI: 10.4061/2011/716859