Cas no 188793-06-8 (Benzoic acid, 4-cyano-2-hydroxy-, methyl ester)

Benzoic acid, 4-cyano-2-hydroxy-, methyl ester is a specialized organic compound featuring a benzoic acid core substituted with a cyano group at the 4-position and a hydroxyl group at the 2-position, esterified with methanol. This structure imparts unique reactivity, making it valuable in synthetic chemistry, particularly as an intermediate in pharmaceuticals and fine chemicals. The presence of both electron-withdrawing (cyano) and electron-donating (hydroxy) groups enhances its utility in regioselective reactions. Its ester functionality improves solubility in organic solvents, facilitating purification and handling. The compound’s stability under mild conditions further supports its use in multi-step synthesis.
Benzoic acid, 4-cyano-2-hydroxy-, methyl ester structure
188793-06-8 structure
Product Name:Benzoic acid, 4-cyano-2-hydroxy-, methyl ester
CAS No:188793-06-8
MF:C9H7NO3
MW:177.156782388687
CID:1380164
PubChem ID:22616130
Update Time:2025-08-05

Benzoic acid, 4-cyano-2-hydroxy-, methyl ester Chemical and Physical Properties

Names and Identifiers

    • Benzoic acid, 4-cyano-2-hydroxy-, methyl ester
    • 188793-06-8
    • Methyl 4-cyano-2-hydroxybenzoate
    • EN300-1615124
    • IZZPQVGOOYLDOD-UHFFFAOYSA-N
    • C90924
    • SCHEMBL5961092
    • Inchi: 1S/C9H7NO3/c1-13-9(12)7-3-2-6(5-10)4-8(7)11/h2-4,11H,1H3
    • InChI Key: IZZPQVGOOYLDOD-UHFFFAOYSA-N
    • SMILES: O(C)C(C1C=CC(C#N)=CC=1O)=O

Computed Properties

  • Exact Mass: 177.04261
  • Monoisotopic Mass: 177.042593085g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 243
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.1
  • Topological Polar Surface Area: 70.3?2

Experimental Properties

  • PSA: 70.32

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Additional information on Benzoic acid, 4-cyano-2-hydroxy-, methyl ester

Benzoic acid, 4-cyano-2-hydroxy-, methyl ester (CAS No. 188793-06-8): A Comprehensive Overview in Modern Chemical Biology

Benzoic acid, 4-cyano-2-hydroxy-, methyl ester, identified by the CAS number 188793-06-8, is a specialized organic compound that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound, characterized by its unique structural features, exhibits a blend of chemical properties that make it a valuable candidate for various applications, particularly in the development of bioactive molecules and therapeutic agents. The presence of both cyano and hydroxyl functional groups, along with the methyl ester moiety, contributes to its diverse reactivity and potential utility in synthetic chemistry and drug design.

The molecular structure of Benzoic acid, 4-cyano-2-hydroxy-, methyl ester consists of a benzoic acid backbone modified with a cyano group at the fourth position and a hydroxyl group at the second position, both of which are further esterified with a methyl group. This configuration imparts distinct electronic and steric properties to the molecule, influencing its interactions with biological targets. The cyano group, being highly polar and electron-withdrawing, can enhance the compound's binding affinity to certain enzymes and receptors, while the hydroxyl and ester groups contribute to hydrogen bonding capabilities and metabolic stability.

In recent years, Benzoic acid, 4-cyano-2-hydroxy-, methyl ester has been explored in several cutting-edge research areas within chemical biology. One notable application lies in its role as a key intermediate in the synthesis of novel heterocyclic compounds. Heterocycles are fundamental scaffolds in medicinal chemistry due to their prevalence in biologically active natural products and synthetic drugs. The structural motifs present in Benzoic acid, 4-cyano-2-hydroxy-, methyl ester provide a versatile platform for constructing more complex molecules with enhanced pharmacological properties.

Moreover, studies have highlighted the potential of this compound as a precursor in the development of bioactive agents targeting inflammatory pathways. The cyano and hydroxyl functional groups are known to modulate enzyme activity through selective interactions with key residues in protein structures. For instance, research has demonstrated that derivatives of benzoic acid can inhibit cyclooxygenase (COX) enzymes, which are pivotal in the production of pro-inflammatory mediators like prostaglandins. The incorporation of additional functional groups into the benzoic acid framework can further refine these inhibitory effects, making compounds like Benzoic acid, 4-cyano-2-hydroxy-, methyl ester promising candidates for anti-inflammatory therapies.

The pharmaceutical industry has also shown interest in Benzoic acid, 4-cyano-2-hydroxy-, methyl ester for its potential role in antimicrobial applications. The structural features of this compound can disrupt bacterial cell membranes or interfere with essential metabolic processes, leading to effective antibacterial activity. Recent advancements in drug discovery have emphasized the need for novel antimicrobial agents due to the rise of antibiotic-resistant strains. Compounds derived from benzoic acid analogs have been investigated for their ability to combat resistant pathogens without triggering widespread toxicity.

Synthetic methodologies for preparing Benzoic acid, 4-cyano-2-hydroxy-, methyl ester have seen significant refinements over the years. Modern synthetic routes often leverage catalytic processes to improve yield and purity while minimizing environmental impact. Transition metal catalysis, for example, has enabled more efficient transformations of starting materials into the desired product. These advancements not only enhance the practicality of producing this compound but also align with global efforts toward sustainable chemistry practices.

The biological activity of Benzoic acid, 4-cyano-2-hydroxy-, methyl ester is further enhanced by its ability to undergo various metabolic transformations within biological systems. These transformations can lead to bioactive derivatives that exhibit different pharmacological profiles compared to the parent compound. Understanding these metabolic pathways is crucial for optimizing drug design and ensuring that therapeutic agents remain effective while minimizing side effects.

In conclusion, Benzoic acid, 4-cyano-2-hydroxy-, methyl ester (CAS No. 188793-06-8) represents a fascinating compound with broad applications in chemical biology and pharmaceutical research. Its unique structural features make it a valuable building block for synthesizing bioactive molecules targeting various diseases. As research continues to uncover new therapeutic possibilities and refine synthetic methodologies, compounds like this are poised to play an increasingly important role in advancing medical science.

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