4-Hydroxynicotinic acid
[CAS# 609-70-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 4-Hydroxynicotinic acid
• Synonyms: 4-Hydroxypyridine-3-carboxylic acid
• Molecular Formula: C₆H₅NO₃
• Molecular Weight: 139.11
• CAS Registry Number: 609-70-1
• EC Number: 210-197-7
• SMILES: C1=CNC=C(C1=O)C(=O)O

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 256-259 °C (Expl.)
• Index of Refraction: 1.579, Calc.^*
• Boiling Point: 312.7±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 142.9±27.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

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
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

4-Hydroxynicotinic acid, with the chemical formula C6H5NO3, is a derivative of nicotinic acid (niacin) where a hydroxyl group (-OH) is attached at the para position of the aromatic ring. This compound belongs to the family of pyridine carboxylic acids and is characterized by its involvement in various chemical and biochemical processes. It has found applications in the synthesis of biologically active compounds and in the development of certain pharmaceutical products.

The discovery of 4-hydroxynicotinic acid is linked to the broader study of pyridine derivatives, especially those with carboxyl groups, which have long been known for their biological activity. The compound is structurally similar to nicotinic acid but differs by the presence of the hydroxyl group. This structural modification alters its chemical properties and expands its potential applications. While the precise date of the compound's discovery is not easily pinpointed, its identification and subsequent study have contributed to the understanding of pyridine carboxylic acids.

One of the primary applications of 4-hydroxynicotinic acid is in the pharmaceutical and biochemical fields. It is considered an important intermediate in the synthesis of various biologically active compounds. Specifically, 4-hydroxynicotinic acid is used in the preparation of certain drugs that have therapeutic effects, particularly those targeting the central nervous system. Research has demonstrated that this compound and its derivatives exhibit certain neuroactive properties, which make them valuable in drug development for conditions such as cognitive disorders or neurodegenerative diseases.

In addition to its use in the synthesis of pharmaceutical agents, 4-hydroxynicotinic acid is also employed in the preparation of various fine chemicals and agricultural chemicals. Its chemical structure allows it to serve as a precursor for the synthesis of herbicides, pesticides, and other agrochemicals. These applications leverage the compound's ability to be chemically modified, producing substances with enhanced efficacy in agricultural and environmental applications.

Moreover, 4-hydroxynicotinic acid plays a role in biochemical research, particularly in studies related to the metabolism of pyridine compounds in living organisms. It has been investigated for its interactions with enzymes involved in vitamin B3 (niacin) metabolism and its potential impact on cellular processes. The compound's biochemical properties make it a subject of interest in the field of nutrition and metabolic health, especially in relation to the understanding of niacin's role in cellular functions and energy metabolism.

In conclusion, 4-hydroxynicotinic acid is a versatile compound with applications across pharmaceutical, agricultural, and biochemical sectors. Its discovery as a derivative of nicotinic acid has allowed it to serve as a precursor for the development of various drugs and agrochemicals. Ongoing research continues to explore its potential uses, particularly in the context of neuroactive compounds and metabolic studies.

References

2024. A terminal metabolite of niacin promotes vascular inflammation and contributes to cardiovascular disease risk. Nature Medicine, 30(2).
DOI: 10.1038/s41591-023-02793-8

2018. 4-Hydroxy-3,5-pyridinedicarboxylic Acids: Synthesis, Complexation Properties Towards Fe(III), Al(III), Cu(II), Zn(II), Human Serum Albumin, and Cellular Toxicity. Journal of Solution Chemistry, 47(1).
DOI: 10.1007/s10953-018-0709-0

2012. Different approaches to the study of chelating agents for iron and aluminium overload pathologies. Analytical and Bioanalytical Chemistry, 405(2-3).
DOI: 10.1007/s00216-012-6468-7