Cas no 196195-42-3 (2-(3-hydroxyphenyl)butanedioic acid)

2-(3-Hydroxyphenyl)butanedioic acid is a substituted aromatic dicarboxylic acid with a hydroxyl group at the meta position of the phenyl ring. This compound is of interest in organic synthesis and pharmaceutical research due to its bifunctional reactivity, combining both carboxylic acid and phenolic hydroxyl groups. Its structure enables versatile applications, including serving as a precursor for fine chemicals or intermediates in drug development. The hydroxyl group enhances solubility in polar solvents, while the dicarboxylic acid moiety allows for further derivatization, such as esterification or amidation. Its balanced hydrophilicity and reactivity make it a useful building block in medicinal chemistry and material science applications.
2-(3-hydroxyphenyl)butanedioic acid structure
196195-42-3 structure
Product Name:2-(3-hydroxyphenyl)butanedioic acid
CAS No:196195-42-3
MF:C10H10O5
MW:210.183403491974
CID:4710041
PubChem ID:71075393
Update Time:2025-05-23

2-(3-hydroxyphenyl)butanedioic acid Chemical and Physical Properties

Names and Identifiers

    • 2-(3-hydroxyphenyl)succinic acid
    • 2-(3-hydroxyphenyl)butanedioic acid
    • Inchi: 1S/C10H10O5/c11-7-3-1-2-6(4-7)8(10(14)15)5-9(12)13/h1-4,8,11H,5H2,(H,12,13)(H,14,15)
    • InChI Key: YBPDFQPNAFMYKI-UHFFFAOYSA-N
    • SMILES: OC(C(CC(=O)O)C1C=CC=C(C=1)O)=O

Computed Properties

  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 4
  • Complexity: 250
  • Topological Polar Surface Area: 94.8

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Additional information on 2-(3-hydroxyphenyl)butanedioic acid

Comprehensive Overview of 2-(3-hydroxyphenyl)butanedioic acid (CAS No. 196195-42-3): Properties, Applications, and Research Insights

2-(3-hydroxyphenyl)butanedioic acid (CAS No. 196195-42-3) is a specialized organic compound with a growing presence in pharmaceutical and biochemical research. This hydroxyphenyl derivative is structurally characterized by a phenyl ring substituted with a hydroxyl group at the meta-position, coupled with a butanedioic acid (succinic acid) side chain. Its unique molecular architecture makes it a valuable intermediate in synthesizing bioactive molecules, particularly in drug discovery and metabolic pathway studies.

Recent trends in green chemistry and sustainable synthesis have amplified interest in compounds like 2-(3-hydroxyphenyl)butanedioic acid. Researchers are exploring its potential as a biobased building block for eco-friendly polymers and pharmaceutical excipients. The compound's carboxylic acid and phenolic hydroxyl functionalities enable diverse chemical modifications, aligning with the demand for multifunctional intermediates in precision medicine.

In analytical chemistry, CAS No. 196195-42-3 has gained attention for its role in HPLC method development and mass spectrometry calibration. Its UV-active aromatic moiety and ionizable groups make it suitable for chromatographic standards. A 2023 study in the Journal of Pharmaceutical Analysis highlighted its utility as a reference material for quantifying phenolic acids in plant extracts, addressing the booming market for natural product standardization.

The compound's structure-activity relationship (SAR) has been investigated in neuroprotective agent development. Molecular docking studies suggest its potential to interact with enzyme active sites involved in oxidative stress regulation. This aligns with current research priorities in neurodegenerative disease therapeutics, where phenolic acids are being evaluated for their antioxidant capacity and blood-brain barrier permeability.

From a regulatory perspective, 2-(3-hydroxyphenyl)butanedioic acid complies with major pharmacopeial standards for impurity profiling. Its well-defined spectroscopic fingerprints (FTIR, NMR) facilitate quality control in GMP manufacturing. The compound's logP value and aqueous solubility data are frequently requested in ADMET prediction queries, reflecting industry needs for computational chemistry inputs.

Emerging applications include its use in metal-chelating formulations for nutritional supplements and as a precursor for bioactive coatings in medical devices. Patent analyses reveal increasing filings incorporating CAS 196195-42-3 in controlled-release systems, particularly for gastrointestinal-targeted delivery of anti-inflammatory compounds.

Ongoing research is exploring the compound's microbial transformation potential using engineered enzymes, a hot topic in white biotechnology. Recent conferences have featured discussions on its role in cascade reactions for chiral synthesis, addressing the pharmaceutical industry's need for stereoselective methodologies.

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