Rhodanine-3-acetic acid
[CAS# 5718-83-2]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs
• Name: Rhodanine-3-acetic acid
• Synonyms: Rhodanine-N-acetic acid; 4-Oxo-2-thioxo-3-thiazolidinylacetic acid
• Molecular Formula: C₅H₅NO₃S₂
• Molecular Weight: 191.22
• CAS Registry Number: 5718-83-2
• EC Number: 227-220-1
• SMILES: C1C(=O)N(C(=S)S1)CC(=O)O

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Melting point: 147 ºC (Expl.)
• Index of Refraction: 1.724, Calc.^*
• Boiling Point: 375.4±44.0 ºC (760 mmHg), Calc.^*
• Flash Point: 180.8±28.4 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovory and Applicatios

Rhodanine-3-acetic acid is a chemical compound belonging to the rhodanine family, which is known for its diverse biological activities and synthetic versatility. Rhodanine derivatives have attracted significant attention in medicinal chemistry due to their wide-ranging pharmacological properties, including antimicrobial, anticancer, and anti-inflammatory effects. Rhodanine-3-acetic acid, in particular, has gained recognition for its potential as a bioactive agent, contributing to the development of novel therapeutic applications.

The discovery of rhodanine-3-acetic acid can be traced back to studies on rhodanine derivatives in the early 20th century, with researchers exploring their potential as sulfur-containing heterocyclic compounds with biological relevance. The acetic acid group attached to the rhodanine ring structure enhances the compound's solubility and stability, making it a promising candidate for various therapeutic applications. Its chemical structure, characterized by a five-membered ring containing sulfur and nitrogen, allows for interactions with a wide array of biological targets.

One of the most significant applications of rhodanine-3-acetic acid is its potential as an anti-inflammatory agent. Inflammation is a key process involved in various chronic diseases, including rheumatoid arthritis, cardiovascular diseases, and neurodegenerative conditions. Rhodanine-3-acetic acid has shown the ability to inhibit pro-inflammatory cytokines and enzymes, thus modulating the immune response and reducing the severity of inflammation. Studies have demonstrated that rhodanine-3-acetic acid can effectively reduce inflammatory markers in animal models, suggesting its potential as a treatment for inflammatory diseases.

In addition to its anti-inflammatory properties, rhodanine-3-acetic acid has demonstrated antimicrobial activity. Bacterial infections remain a significant global health challenge, and the development of new antimicrobial agents is critical to combat the rise of antibiotic-resistant strains. Rhodanine-3-acetic acid has shown effectiveness against various bacterial species, including both Gram-positive and Gram-negative bacteria. This antimicrobial activity is thought to arise from the compound's ability to interfere with microbial cell functions, including cell wall synthesis and protein production, making it a potential candidate for the development of new antibacterial therapies.

Rhodanine-3-acetic acid has also been explored for its anticancer potential. Several studies have highlighted its ability to inhibit the growth of cancer cells by inducing apoptosis (programmed cell death). The compound has been found to interfere with various signaling pathways involved in cell proliferation, thus suppressing tumor growth. Additionally, rhodanine-3-acetic acid has shown synergistic effects when used in combination with other chemotherapeutic agents, further enhancing its potential in cancer treatment.

Another area of interest for rhodanine-3-acetic acid is its role in modulating metabolic diseases, particularly diabetes. Research has indicated that rhodanine-3-acetic acid may influence insulin sensitivity and glucose metabolism. This effect makes it a candidate for the treatment of Type 2 diabetes, a disease characterized by insulin resistance and impaired glucose regulation. While further studies are needed to fully understand its mechanisms of action, early findings suggest that rhodanine-3-acetic acid could contribute to the development of new therapeutic strategies for managing metabolic diseases.

In summary, rhodanine-3-acetic acid is a bioactive compound with significant therapeutic potential. Its anti-inflammatory, antimicrobial, anticancer, and metabolic effects make it an attractive candidate for the development of new drugs. As research continues to explore its diverse applications, rhodanine-3-acetic acid may contribute to the advancement of novel treatments for a wide range of diseases, from chronic inflammatory disorders to cancer and metabolic conditions.