Production Method 1

150-19-6

3147-64-6

90111-34-5

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Diethyl ether

Reference

Heteroatom-facilitated lithiations

Gschwend, Heinz W.; Rodriguez, Herman R., Organic Reactions (Hoboken, 1979, 26,

2-Hydroxy-6-methoxybenzoic acid Raw materials

• 3-Methoxyphenol

2-Hydroxy-6-methoxybenzoic acid Preparation Products

• 4-Hydroxy-2-methoxybenzoic acid (90111-34-5)
• 2-Hydroxy-6-methoxybenzoic acid (3147-64-6)

• 1. 76. Derivatives of 6-aminopenicillanic acid. Part V. Analogues of 2,6-dimethoxyphenylpenicillin with enhanced stability towards acids
  F. P. Doyle,J. H. C. Nayler,H. R. J. Waddington,J. C. Hanson,G. R. Thomas J. Chem. Soc. 1963 497
• 2. 670. The synthesis of γ-resorcylic acid (2 : 6-dihydroxybenzoic acid)
  N. J. Cartwright,J. Idris Jones,Diana Marmion J. Chem. Soc. 1952 3499
• 3. XCI.—The constituents of Gloriosa superba
  Hubert William Bentley Clewer,Stanley Joseph Green,Frank Tutin J. Chem. Soc. Trans. 1915 107 835
• 4. 705. Griseofulvin. Part XII. Position of the aryl methyl ether linkage, labile to aqueous alkali
  L. A. Duncanson,John Frederick Grove,J. Macmillan,T. P. C. Mulholland J. Chem. Soc. 1957 3555
• 5. Expanding antibiotic chemical space around the nidulin pharmacophore
  Mahmud T. Morshed,Daniel Vuong,Andrew Crombie,Alastair E. Lacey,Peter Karuso,Ernest Lacey,Andrew M. Piggott Org. Biomol. Chem. 2018 16 3038

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives O-methoxybenzoic acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Introduction to 2-Hydroxy-6-methoxybenzoic acid (CAS No. 3147-64-6)

2-Hydroxy-6-methoxybenzoic acid, with the chemical formula C?H?O?, is a versatile organic compound belonging to the class of methoxyphenols. Its molecular structure features a hydroxyl group at the 2-position and a methoxy group at the 6-position of a benzoic acid core, making it a valuable intermediate in pharmaceutical synthesis and chemical research. This compound has garnered significant attention in recent years due to its diverse biological activities and potential applications in drug development.

The CAS number 3147-64-6 provides a unique identifier for this substance, ensuring precise classification and reference in scientific literature. As a derivative of benzoic acid, 2-Hydroxy-6-methoxybenzoic acid inherits certain properties of its parent molecule while exhibiting distinct characteristics due to the substitution pattern. The presence of both hydroxyl and methoxy groups enhances its reactivity, making it a useful building block in organic synthesis.

In recent years, 2-Hydroxy-6-methoxybenzoic acid has been extensively studied for its potential pharmacological properties. Research has highlighted its role as an antioxidant, which is crucial in combating oxidative stress and inflammation associated with various chronic diseases. The compound's ability to scavenge free radicals has been demonstrated in multiple in vitro studies, suggesting its therapeutic potential.

Moreover, 2-Hydroxy-6-methoxybenzoic acid has shown promise as a precursor in the synthesis of more complex molecules with targeted biological activities. For instance, it has been utilized in the preparation of derivatives that exhibit anti-inflammatory and analgesic effects. These findings have spurred further investigation into its structural analogs, aiming to optimize its pharmacokinetic and pharmacodynamic profiles.

Recent advancements in computational chemistry have enabled researchers to predict the binding affinity of 2-Hydroxy-6-methoxybenzoic acid to various biological targets. Molecular docking studies have identified potential interactions with enzymes and receptors involved in metabolic pathways, offering insights into its mechanism of action. This computational approach has complemented experimental investigations, providing a more comprehensive understanding of the compound's biological relevance.

The pharmaceutical industry has taken note of these findings, leading to increased interest in developing novel drugs based on 2-Hydroxy-6-methoxybenzoic acid or its derivatives. Several clinical trials are underway to evaluate its efficacy and safety in treating conditions such as arthritis and neurodegenerative disorders. The compound's favorable safety profile observed in preclinical studies has bolstered confidence among researchers and developers.

Beyond pharmaceutical applications, 2-Hydroxy-6-methoxybenzoic acid finds utility in other industries as well. Its antioxidant properties make it a suitable candidate for use in cosmetic formulations, where it can help protect skin cells from damage caused by environmental stressors. Additionally, it is being explored as an additive in food products due to its potential health benefits.

The synthesis of 2-Hydroxy-6-methoxybenzoic acid can be achieved through various chemical pathways, including esterification and hydrolysis reactions. Recent innovations in green chemistry have focused on developing more sustainable methods for producing this compound, minimizing waste and reducing environmental impact. Such efforts align with global initiatives to promote eco-friendly chemical processes.

In conclusion, 2-Hydroxy-6-methoxybenzoic acid (CAS No. 3147-64-6) is a multifaceted compound with significant potential across multiple domains. Its biological activities, synthetic versatility, and industrial applications make it a subject of intense research interest. As scientific understanding continues to evolve, the role of this compound is expected to expand further, contributing to advancements in medicine and beyond.

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