2-Amino-4,5-dimethoxybenzoic acid
[CAS# 5653-40-7]

Identification

• Classification: API >> Antineoplastic agents
• Name: 2-Amino-4,5-dimethoxybenzoic acid
• Synonyms: 4,5-Dimethoxyanthranilic acid
• Molecular Formula: C₉H₁₁NO₄
• Molecular Weight: 197.19
• CAS Registry Number: 5653-40-7
• EC Number: 227-095-3
• SMILES: COC1=C(C=C(C(=C1)C(=O)O)N)OC

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: 155-158 ºC (decomp.)
• Index of Refraction: 1.582, Calc.^*
• Boiling Point: 358.6±42.0 ºC (760 mmHg), Calc.^*
• Flash Point: 170.7±27.9 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

Discovory and Applicatios

2-Amino-4,5-dimethoxybenzoic acid, also known as homoveratric acid, is an aromatic amino acid derivative that has attracted interest due to its potential applications in pharmaceuticals and organic synthesis. The compound features two methoxy groups and an amino group on a benzene ring, which contributes to its chemical reactivity and biological activity.

The discovery of 2-amino-4,5-dimethoxybenzoic acid can be traced back to the early 20th century when researchers were investigating the properties of substituted benzoic acids. Initial studies focused on the synthesis of various methoxy-substituted benzoic acids and their derivatives. The method of synthesis typically involves the introduction of methoxy groups onto the benzene ring, followed by the addition of an amino group, resulting in the formation of the desired compound. Over the years, advancements in organic chemistry have refined these synthesis techniques, enabling higher yields and purities of the product.

One of the notable applications of 2-amino-4,5-dimethoxybenzoic acid is its role as an intermediate in the synthesis of pharmaceuticals. Due to its functional groups, it serves as a building block for more complex molecules, particularly in the development of drugs targeting various biological pathways. Its structural features allow for further modifications, making it versatile in medicinal chemistry.

In the realm of research, 2-amino-4,5-dimethoxybenzoic acid has shown promise as a compound with potential biological activities. Studies have indicated that it possesses antioxidant properties, which may contribute to its role in protecting cells from oxidative stress. This property is particularly relevant in the context of diseases where oxidative damage is a key factor, such as neurodegenerative disorders and cardiovascular diseases.

Moreover, this compound has been explored for its potential in the development of agrochemicals. Research indicates that derivatives of 2-amino-4,5-dimethoxybenzoic acid may exhibit herbicidal and fungicidal properties, contributing to agricultural practices aimed at improving crop yields and sustainability. The ability to modify the compound allows chemists to tailor its biological activity, leading to the discovery of new agrochemical agents.

The synthesis of 2-amino-4,5-dimethoxybenzoic acid often utilizes methodologies such as methylation followed by amination, allowing for the efficient introduction of the methoxy and amino groups. Ongoing research aims to optimize these synthetic routes to produce the compound in a more environmentally friendly manner, reflecting a growing emphasis on sustainable chemistry.

In conclusion, 2-amino-4,5-dimethoxybenzoic acid is a significant chemical compound with diverse applications in pharmaceuticals and agriculture. Its discovery and subsequent exploration highlight the importance of substituted benzoic acids in chemical synthesis and biological research. Continued studies on this compound may lead to novel therapeutic agents and sustainable agricultural solutions.

References

2022. Mild protocol for synthesis of BIX-01294 using 2-amino-4,5-dimethoxybenzoic acid. Russian Journal of General Chemistry, 92(12).
DOI: 10.1007/s11172-022-3678-9

2020. Quinazolinone derivatives from 2-amino-4,5-dimethoxybenzoic acid for antiamoebic activity. Parasitology Research, 119(8).
DOI: 10.1007/s00436-020-06710-7

2020. Quinoline/cinnamic acid hybrids as amyloid-beta aggregation inhibitors. Monatshefte für Chemie, 151(7).
DOI: 10.1007/s00706-020-02609-2