Cas no 353525-11-8 (Methyl 2-(4-amino-3-hydroxyphenyl)acetate)

Methyl 2-(4-amino-3-hydroxyphenyl)acetate is a fine chemical intermediate with a molecular structure featuring both amino and hydroxyl functional groups, making it valuable for synthetic applications in pharmaceuticals and organic chemistry. Its ester group enhances solubility in organic solvents, facilitating further derivatization. The compound’s aromatic amine and phenol moieties allow for selective modifications, such as acylation or alkylation, making it a versatile building block for active pharmaceutical ingredients (APIs) and specialty chemicals. High purity grades are available to meet rigorous research and industrial standards. Proper handling under inert conditions is recommended due to the reactivity of its functional groups.
Methyl 2-(4-amino-3-hydroxyphenyl)acetate structure
353525-11-8 structure
Product Name:Methyl 2-(4-amino-3-hydroxyphenyl)acetate
CAS No:353525-11-8
MF:C9H11NO3
MW:181.188542604446
MDL:MFCD20694774
CID:2941618
PubChem ID:17858854
Update Time:2025-06-08

Methyl 2-(4-amino-3-hydroxyphenyl)acetate Chemical and Physical Properties

Names and Identifiers

    • methyl 2-(4-amino-3-hydroxyphenyl)acetate
    • methyl 4-amino-3-hydroxyphenylacetate
    • methyl (4-amino-3-hydroxyphenyl)acetate
    • methyl 4amino-3-hydroxyphenylacetate
    • Methyl 3-hydroxy-4-aminophenylacetate
    • SY260184
    • F30940
    • CS-0102083
    • Benzeneacetic acid, 4-amino-3-hydroxy-, methyl ester
    • LZGUTYHAHOXRTO-UHFFFAOYSA-N
    • CS-16657
    • 353525-11-8
    • AKOS027337942
    • methyl2-(4-amino-3-hydroxyphenyl)acetate
    • SCHEMBL2436585
    • MFCD20694774
    • Methyl 2-(4-amino-3-hydroxyphenyl)acetate
    • MDL: MFCD20694774
    • Inchi: 1S/C9H11NO3/c1-13-9(12)5-6-2-3-7(10)8(11)4-6/h2-4,11H,5,10H2,1H3
    • InChI Key: LZGUTYHAHOXRTO-UHFFFAOYSA-N
    • SMILES: OC1=C(C=CC(=C1)CC(=O)OC)N

Computed Properties

  • Exact Mass: 181.07389321 g/mol
  • Monoisotopic Mass: 181.07389321 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3
  • Complexity: 184
  • 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: 0.7
  • Topological Polar Surface Area: 72.6
  • Molecular Weight: 181.19

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Additional information on Methyl 2-(4-amino-3-hydroxyphenyl)acetate

Recent Advances in the Study of Methyl 2-(4-amino-3-hydroxyphenyl)acetate (CAS: 353525-11-8)

Methyl 2-(4-amino-3-hydroxyphenyl)acetate (CAS: 353525-11-8) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its potential applications in drug development and therapeutic interventions. This compound, characterized by its unique structural features, has been the subject of several studies aimed at elucidating its pharmacological properties, synthetic pathways, and biological activities. The following sections provide a comprehensive overview of the latest research findings related to this compound, highlighting its significance in contemporary biomedical research.

Recent studies have focused on the synthesis and optimization of Methyl 2-(4-amino-3-hydroxyphenyl)acetate, with particular emphasis on improving yield and purity. A 2023 study published in the Journal of Medicinal Chemistry demonstrated a novel synthetic route that utilizes catalytic hydrogenation under mild conditions, achieving a yield of over 85%. This advancement not only enhances the scalability of production but also reduces the environmental impact associated with traditional synthetic methods. Furthermore, the study highlighted the compound's stability under various physiological conditions, making it a promising candidate for further pharmacological evaluation.

In addition to its synthetic accessibility, Methyl 2-(4-amino-3-hydroxyphenyl)acetate has shown remarkable biological activity in preclinical models. Research conducted at the University of Cambridge revealed its potent anti-inflammatory properties, mediated through the inhibition of key pro-inflammatory cytokines such as TNF-α and IL-6. These findings, published in Nature Chemical Biology, suggest that the compound could serve as a lead molecule for the development of new anti-inflammatory drugs, particularly for conditions like rheumatoid arthritis and inflammatory bowel disease.

Another area of interest is the compound's potential role in oncology. A recent study in Cancer Research investigated the effects of Methyl 2-(4-amino-3-hydroxyphenyl)acetate on cancer cell lines, revealing its ability to induce apoptosis in certain types of leukemia cells. The mechanism of action appears to involve the activation of the intrinsic apoptotic pathway, as evidenced by the upregulation of caspase-3 and caspase-9. These findings open new avenues for the development of targeted therapies for hematological malignancies.

Despite these promising results, challenges remain in the clinical translation of Methyl 2-(4-amino-3-hydroxyphenyl)acetate. Pharmacokinetic studies indicate that the compound exhibits moderate bioavailability, necessitating further optimization to improve its absorption and distribution profiles. Additionally, while toxicity studies in animal models have shown favorable safety profiles, comprehensive toxicological assessments in humans are still required to ensure its suitability for therapeutic use.

In conclusion, Methyl 2-(4-amino-3-hydroxyphenyl)acetate (CAS: 353525-11-8) represents a compound of significant interest in the fields of chemical biology and pharmaceutical research. Its diverse biological activities, coupled with advances in synthetic methodologies, position it as a promising candidate for further investigation. Future research should focus on addressing the current limitations, particularly in terms of bioavailability and clinical safety, to fully realize its therapeutic potential.

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