2-Hydroxy-4,5-dimethoxybenzoic acid
[CAS# 5722-93-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 2-Hydroxy-4,5-dimethoxybenzoic acid
• Synonyms: 4,5-Dimethoxysalicylic acid
• Molecular Formula: C₉H₁₀O₅
• Molecular Weight: 198.17
• CAS Registry Number: 5722-93-0
• SMILES: COC1=C(C=C(C(=C1)C(=O)O)O)OC

Properties

• Solubility: Slightly soluble (4 g/L) (25 °C), Calc.^*
• Density: 1.335±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 213-214 °C (decomp)^**
• Index of Refraction: 1.566, Calc.^*
• Boiling Point: 361.5±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 146.7±21.4 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Head, Frank S. H.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

2-Hydroxy-4,5-dimethoxybenzoic acid is an aromatic compound that belongs to the class of methoxy-substituted benzoic acids. This compound is characterized by a hydroxyl group (-OH) at the 2-position and two methoxy groups (-OCH3) at the 4- and 5-positions on the benzene ring. The unique arrangement of functional groups in 2-hydroxy-4,5-dimethoxybenzoic acid imparts specific chemical and physical properties that make it an interesting target for research in several fields, including medicinal chemistry, material science, and organic synthesis.

The discovery of 2-hydroxy-4,5-dimethoxybenzoic acid can be traced back to the ongoing exploration of naturally occurring and synthetically derived compounds with potential biological activity. Methoxy-substituted benzoic acids are known for their diverse range of activities, including anti-inflammatory, antimicrobial, and antioxidant properties. The hydroxyl group, which is a common motif in many bioactive molecules, provides the compound with the ability to form hydrogen bonds, potentially enhancing its interaction with biological targets. Meanwhile, the methoxy groups contribute to the compound's hydrophobicity and stability.

The synthesis of 2-hydroxy-4,5-dimethoxybenzoic acid generally involves the functionalization of a benzoic acid derivative with the required methoxy and hydroxyl groups. One common synthetic approach is the methylation of 2-hydroxybenzoic acid using dimethyl sulfate or methyl iodide as a methylating agent to introduce the methoxy groups at the 4 and 5 positions. The selective introduction of these groups is essential to the compound's structure, as the position of the hydroxyl and methoxy groups significantly influences the compound's reactivity and biological activity.

2-Hydroxy-4,5-dimethoxybenzoic acid has potential applications in the development of pharmaceutical compounds. Due to the presence of the hydroxyl and methoxy groups, it is a candidate for use in medicinal chemistry, where it could be explored for anti-inflammatory or antioxidant properties. The presence of the hydroxyl group allows for interactions with protein targets via hydrogen bonding, which may enhance its efficacy in biological systems. Additionally, its methoxy substituents could contribute to improved solubility and stability, which are desirable properties in drug design.

In material science, 2-hydroxy-4,5-dimethoxybenzoic acid could be explored as a building block for the synthesis of more complex molecules. Its unique functional groups offer opportunities for designing new materials with specific properties, such as increased resistance to degradation or enhanced interactions with other materials. The compound could also be considered for use in organic electronics or as a component in the design of optoelectronic materials due to the presence of the aromatic ring and functional groups that influence its electronic properties.

In conclusion, 2-hydroxy-4,5-dimethoxybenzoic acid is a versatile compound with a variety of potential applications in both the pharmaceutical and material science fields. The unique combination of functional groups on the aromatic ring makes it a valuable target for further research aimed at exploiting its biological and material properties.

References

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