Cas no 24393-54-2 (Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate)

Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate is a cinnamate ester derivative characterized by its (E)-configured double bond and methoxy-substituted aromatic ring. This compound is commonly utilized as a key intermediate in organic synthesis, particularly in the preparation of fine chemicals, pharmaceuticals, and flavoring agents. Its structural features, including the conjugated system and electron-donating methoxy group, enhance reactivity in Michael additions, cyclizations, and other transformations. The ethyl ester moiety improves solubility in organic solvents, facilitating handling in synthetic workflows. High purity grades are available for research and industrial applications, ensuring reproducibility in reactions. Its stability under standard conditions makes it a practical choice for storage and use in laboratory settings.
Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate structure
24393-54-2 structure
Product Name:Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate
CAS No:24393-54-2
MF:C12H14O3
MW:206.237763881683
MDL:MFCD02149443
CID:268552
PubChem ID:5388518
Update Time:2025-05-28

Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate Chemical and Physical Properties

Names and Identifiers

    • 2-Propenoic acid,3-(2-methoxyphenyl)-, ethyl ester, (2E)-
    • Ethyl (E)-o-methoxycinnamate
    • ethyl (2E)-3-(2-methoxyphenyl)prop-2-enoate
    • (E)-ETHYL 3-(2-METHOXYPHENYL)ACRYLATE
    • PK04_181102
    • EINECS 246-219-7
    • Z53837010
    • CS-0035692
    • Ethyl (E)-3-(2-methoxyphenyl)acrylate
    • Ethyl o-methoxycinnamate
    • BRD-K54328920-001-01-0
    • 33877-05-3
    • BS-41746
    • (E)-ETHYL3-(2-METHOXYPHENYL)ACRYLATE
    • methoxy ethyl cinnamate
    • ethyl (E)-3-(2-methoxyphenyl)prop-2-enoate
    • EINECS 251-710-4
    • W11624
    • Ethyl (2E)-3-(2-methoxyphenyl)-2-propenoate
    • Ethyl 3-(2-methoxyphenyl)acrylate
    • 24393-54-2
    • NSC636700
    • MFCD02149443
    • NSC-636700
    • EN300-1453815
    • DTXSID201264009
    • SCHEMBL15188
    • NS00050555
    • ATAFSLBAINHGTN-CMDGGOBGSA-N
    • STL477112
    • Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate
    • MDL: MFCD02149443
    • Inchi: 1S/C12H14O3/c1-3-15-12(13)9-8-10-6-4-5-7-11(10)14-2/h4-9H,3H2,1-2H3/b9-8+
    • InChI Key: ATAFSLBAINHGTN-CMDGGOBGSA-N
    • SMILES: O(C)C1C=CC=CC=1/C=C/C(=O)OCC

Computed Properties

  • Exact Mass: 206.09432
  • Monoisotopic Mass: 206.094294
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 5
  • Complexity: 223
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 35.5
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing

Experimental Properties

  • Density: 1.08
  • Boiling Point: 311.4°Cat760mmHg
  • Flash Point: 127.3°C
  • Refractive Index: 1.539
  • PSA: 35.53

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Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate Related Literature

Additional information on Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate

Recent Advances in the Study of Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate (CAS: 24393-54-2) in Chemical Biology and Pharmaceutical Research

Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate (CAS: 24393-54-2) is a cinnamic acid derivative that has garnered significant attention in recent years due to its potential applications in medicinal chemistry and drug development. This compound, characterized by its α,β-unsaturated ester moiety and methoxy-substituted aromatic ring, has been the subject of numerous studies exploring its biological activities, synthetic pathways, and pharmacological properties. The latest research highlights its role as a versatile scaffold for the design of novel therapeutic agents, particularly in the areas of anti-inflammatory, anticancer, and antimicrobial drug discovery.

Recent studies have focused on the synthesis and optimization of Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate derivatives to enhance their bioactivity and pharmacokinetic profiles. A 2023 publication in the Journal of Medicinal Chemistry demonstrated that structural modifications at the ester group and the aromatic ring significantly influence the compound's binding affinity to target proteins, such as cyclooxygenase-2 (COX-2) and histone deacetylases (HDACs). These findings underscore the compound's potential as a lead structure for developing selective enzyme inhibitors with reduced off-target effects.

In addition to its pharmacological applications, Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate has been investigated for its role in chemical biology as a fluorescent probe and a photoaffinity labeling agent. A study published in ACS Chemical Biology (2024) utilized this compound to develop a novel probe for real-time imaging of intracellular reactive oxygen species (ROS) in cancer cells. The probe's high selectivity and sensitivity were attributed to the unique electronic properties conferred by the methoxyphenyl and α,β-unsaturated ester functionalities, enabling precise detection of ROS dynamics in live cells.

The compound's mechanism of action has also been elucidated through advanced computational and experimental techniques. Molecular docking and molecular dynamics simulations, as reported in a 2024 Nature Communications article, revealed that Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate interacts with key residues in the active sites of target enzymes, stabilizing specific conformations that inhibit their catalytic activity. These insights have paved the way for rational drug design approaches aimed at optimizing the compound's therapeutic efficacy.

Despite these advancements, challenges remain in the clinical translation of Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate-based therapeutics. Issues such as metabolic stability, bioavailability, and potential toxicity need to be addressed through further preclinical studies. Ongoing research is exploring prodrug strategies and nanoparticle-based delivery systems to overcome these limitations, as highlighted in a recent review in Advanced Drug Delivery Reviews (2024).

In conclusion, Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate (CAS: 24393-54-2) represents a promising candidate for drug development and chemical biology applications. Its versatile chemical structure and diverse biological activities make it a valuable tool for researchers aiming to discover new therapeutic agents and elucidate complex biological mechanisms. Future studies should focus on optimizing its pharmacological properties and advancing it through the drug development pipeline to realize its full potential in clinical settings.

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