Cas no 103987-53-7 (3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid)

3-(3,5-Dimethoxyphenyl)-2-oxopropanoic acid is a specialized organic compound featuring a dimethoxyphenyl group attached to a 2-oxopropanoic acid backbone. This structure imparts unique reactivity, making it valuable as an intermediate in synthetic organic chemistry, particularly in the preparation of pharmaceuticals and fine chemicals. The presence of both ketone and carboxylic acid functional groups allows for versatile derivatization, enabling applications in heterocyclic synthesis and medicinal chemistry research. Its dimethoxy substitution pattern enhances solubility in organic solvents, facilitating purification and handling. The compound’s well-defined molecular architecture ensures consistent performance in multi-step synthetic routes, supporting the development of complex bioactive molecules.
3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid structure
103987-53-7 structure
Product Name:3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid
CAS No:103987-53-7
MF:C11H12O5
MW:224.209983825684
MDL:MFCD12165962
CID:2862612
PubChem ID:14925212
Update Time:2025-05-21

3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid Chemical and Physical Properties

Names and Identifiers

    • Benzenepropanoic acid, 3,5-dimethoxy-.alpha.-oxo-
    • ARJ102867
    • 3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid
    • Benzenepropanoic acid, 3,5-dimethoxy-alpha-oxo-
    • MDL: MFCD12165962
    • Inchi: 1S/C11H12O5/c1-15-8-3-7(4-9(6-8)16-2)5-10(12)11(13)14/h3-4,6H,5H2,1-2H3,(H,13,14)
    • InChI Key: YJHQQHWBGDAHDP-UHFFFAOYSA-N
    • SMILES: O(C)C1C=C(C=C(C=1)CC(C(=O)O)=O)OC

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 5
  • Complexity: 251
  • XLogP3: 1.2
  • Topological Polar Surface Area: 72.8

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Additional information on 3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid

Professional Introduction to 3-(3,5-dimethoxyphenyl)-2-oxopropanoic Acid (CAS No. 103987-53-7)

3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid, with the chemical formula C10H12O4, is a significant compound in the field of pharmaceutical chemistry and biochemistry. This compound, identified by its CAS number 103987-53-7, has garnered attention due to its unique structural properties and potential applications in drug development. The presence of two methoxy groups at the 3rd and 5th positions of the phenyl ring, along with the α-keto acid functionality, makes it a versatile intermediate in organic synthesis and a candidate for further exploration in medicinal chemistry.

The compound's structure, featuring a benzylic α-keto acid moiety, suggests potential reactivity that could be exploited in various synthetic pathways. This reactivity is particularly intriguing for researchers working on the development of novel therapeutic agents. The methoxy substituents not only influence the electronic properties of the aromatic ring but also contribute to the compound's solubility and metabolic stability, which are crucial factors in drug design.

In recent years, there has been a growing interest in α-keto acids as key building blocks in the synthesis of bioactive molecules. These compounds are widely recognized for their ability to participate in various organic transformations, including condensation reactions, Michael additions, and enolate-mediated processes. The specific arrangement of functional groups in 3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid makes it an attractive candidate for exploring new synthetic strategies and developing innovative pharmaceuticals.

One of the most compelling aspects of this compound is its potential role in the synthesis of enzyme inhibitors. α-Keto acids have been shown to act as substrates or inhibitors for various enzymes, making them valuable tools in drug discovery. For instance, studies have demonstrated that derivatives of α-keto acids can interact with enzymes such as ketolases and transaminases, which are involved in metabolic pathways relevant to several diseases. The methoxy-substituted phenyl ring in 3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid could enhance binding affinity and selectivity when designed as an inhibitor.

The pharmaceutical industry has increasingly focused on developing small-molecule inhibitors to modulate enzyme activity. These inhibitors can serve as therapeutic agents by blocking or enhancing specific enzymatic reactions. The structural features of 3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid, particularly its ability to form hydrogen bonds and engage in π-stacking interactions with biological targets, make it a promising candidate for this purpose. Additionally, the compound's solubility profile could be advantageous for formulating oral or injectable drugs.

Recent advances in computational chemistry have further enhanced the ability to predict the biological activity of small molecules like 3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid. Molecular docking studies have been instrumental in understanding how this compound interacts with biological targets at the atomic level. These studies often reveal key interactions that can be optimized to improve drug efficacy and reduce side effects. The methoxy groups on the phenyl ring are particularly important for these interactions, as they can modulate electronic effects and hydrogen bonding patterns.

In addition to its potential as an enzyme inhibitor, 3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid may also find applications in materials science and industrial chemistry. Its unique structural features make it a suitable candidate for developing novel polymers or specialty chemicals. For instance, derivatives of this compound could be used to create high-performance resins or coatings with enhanced thermal stability and mechanical strength.

The synthesis of 3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid presents an interesting challenge for organic chemists due to its complex functionalization pattern. However, recent methodologies have made it more accessible than ever before. Catalytic asymmetric synthesis techniques have enabled the production of enantiomerically pure forms of this compound, which is crucial for pharmaceutical applications where stereochemistry plays a critical role.

The growing body of research on α-keto acids underscores their importance as versatile chemical entities. Studies have shown that these compounds can be readily modified to produce a wide range of derivatives with distinct biological activities. This flexibility makes them valuable tools for both academic research and industrial applications. The work done on compounds like 3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid contributes significantly to our understanding of how structure influences function at the molecular level.

In conclusion, 3-(3,5-dimethoxyphenyl)-2-oxopropanoic acid (CAS No. 103987-53-7) is a multifaceted compound with broad applications in pharmaceutical chemistry and beyond. Its unique structural features make it an attractive candidate for drug development, materials science, and industrial chemistry. As research continues to uncover new synthetic methods and biological activities associated with α-keto acids like this one, we can expect even more innovative uses to emerge from this class of compounds.

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