Cas no 188545-72-4 (m-Ethoxycinnamic Acid)

m-Ethoxycinnamic Acid is a substituted cinnamic acid derivative featuring a methoxy group at the meta position of the aromatic ring. This compound is widely utilized in organic synthesis, particularly as an intermediate in the production of pharmaceuticals, fragrances, and UV-absorbing agents. Its conjugated double bond and aromatic system contribute to its reactivity in condensation and coupling reactions. The meta-substitution pattern offers distinct electronic and steric properties, making it valuable for fine-tuning molecular structures in medicinal chemistry. m-Ethoxycinnamic Acid is characterized by its high purity and stability, ensuring consistent performance in synthetic applications. It is typically supplied as a crystalline solid with well-documented solubility and spectroscopic data for precise formulation.
m-Ethoxycinnamic Acid structure
m-Ethoxycinnamic Acid structure
Product Name:m-Ethoxycinnamic Acid
CAS No:188545-72-4
MF:C11H12O3
MW:192.211183547974
MDL:MFCD00016843
CID:1383456
PubChem ID:5709602
Update Time:2025-06-08

m-Ethoxycinnamic Acid Chemical and Physical Properties

Names and Identifiers

    • (2E)-3-(3-Ethoxyphenyl)acrylic acid
    • 3-(3-ETHOXYPHENYL)ACRYLIC ACID
    • DOEYODSOYOGJQH-VOTSOKGWSA-N
    • (2E)-3-(3-ethoxyphenyl)prop-2-enoic acid
    • HMS2732N03
    • Z2587996047
    • (E)-3-(3-Ethoxyphenyl)acrylic acid
    • 103986-73-8
    • 3-Ethoxycinnamic acid, predominantly trans
    • J-001084
    • ALBB-006574
    • CHEMBL1464150
    • Trans-3-Ethoxycinnamic Acid
    • (E)-3-(3-ethoxyphenyl)prop-2-enoic acid
    • SMR000315100
    • SCHEMBL764029
    • PS-4508
    • EN300-315326
    • 188545-72-4
    • (2E)-3-(3-ethoxyphenyl)prop-2-enoic acid, E
    • MLS000673859
    • AKOS001476038
    • MFCD00016843
    • EN300-1867322
    • BBL022449
    • STK504018
    • CS-0449374
    • 3-Ethoxycinnamic acid, predominantly trans, 97%
    • F78671
    • TRANS-3-ETHOXYCINNAMICACID
    • m-Ethoxycinnamic Acid
    • MDL: MFCD00016843
    • Inchi: 1S/C11H12O3/c1-2-14-10-5-3-4-9(8-10)6-7-11(12)13/h3-8H,2H2,1H3,(H,12,13)/b7-6+
    • InChI Key: DOEYODSOYOGJQH-VOTSOKGWSA-N
    • SMILES: O(CC)C1C=CC=C(/C=C/C(=O)O)C=1

Computed Properties

  • Exact Mass: 192.07866
  • Monoisotopic Mass: 192.078644241g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 4
  • Complexity: 211
  • 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
  • XLogP3: 2.4
  • Topological Polar Surface Area: 46.5?2

Experimental Properties

  • PSA: 46.53

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m-Ethoxycinnamic Acid Related Literature

Additional information on m-Ethoxycinnamic Acid

Introduction to m-Ethoxycinnamic Acid (CAS No. 188545-72-4)

m-Ethoxycinnamic acid, with the chemical formula C10H10O3 and CAS number 188545-72-4, is a versatile organic compound that has garnered significant attention in the field of pharmaceutical chemistry and biomedicine. This compound, a derivative of cinnamic acid, features an ethoxy group at the meta position, which imparts unique chemical and biological properties. Its molecular structure combines the aromatic stability of the phenyl ring with the functional reactivity of the carboxylic acid and ester groups, making it a valuable intermediate in synthetic chemistry and a potential candidate for various therapeutic applications.

The structure of m-ethoxycinnamic acid influences its interactions with biological targets, making it a subject of interest in drug discovery. The presence of both hydrophobic and hydrophilic regions in its molecule allows for favorable solubility profiles, which is crucial for formulation development in medicinal applications. Researchers have been exploring its utility in designing novel compounds that could modulate biological pathways associated with inflammation, oxidative stress, and cellular signaling.

In recent years, m-ethoxycinnamic acid has been studied for its potential role in developing anti-inflammatory agents. The meta-substituted aromatic ring enhances its ability to interact with enzymes such as cyclooxygenase (COX) and lipoxygenase (LOX), which are key players in the inflammatory response. Preclinical studies have suggested that derivatives of m-ethoxycinnamic acid may exhibit reduced side effects compared to traditional nonsteroidal anti-inflammatory drugs (NSAIDs) by selectively inhibiting these enzymes.

Additionally, m-Ethoxycinnamic Acid has shown promise in the field of cosmetics and skincare due to its antioxidant properties. The ethoxy group contributes to stabilizing reactive oxygen species (ROS), thereby protecting skin cells from oxidative damage caused by environmental stressors such as UV radiation and pollutants. This property makes it a popular ingredient in anti-aging formulations and photoprotective creams. Recent clinical trials have demonstrated its efficacy in improving skin texture and reducing fine lines when incorporated into topical preparations.

The pharmaceutical industry has also explored m-ethoxycinnamic acid as a building block for more complex molecules. Its reactive sites allow for further functionalization through esterification, amidation, or coupling reactions, enabling the synthesis of novel drug candidates. For instance, researchers have modified its structure to develop protease inhibitors that could be useful in treating chronic diseases such as cancer and neurodegenerative disorders. The flexibility offered by its chemical framework makes it a valuable scaffold for medicinal chemists.

From a synthetic chemistry perspective, CAS No. 188545-72-4 represents an interesting case study due to the challenges and opportunities it presents in asymmetric synthesis. The meta-substituted cinnamic acid derivative can be synthesized through various pathways, including cross-coupling reactions and catalytic hydrogenation. Advances in green chemistry have led to more sustainable methods for producing this compound, emphasizing the importance of environmental considerations in industrial applications.

The biological activity of m-Ethoxycinnamic Acid extends beyond inflammation and antioxidant effects. Emerging research suggests that it may influence metabolic pathways by interacting with receptors such as PPARs (Peroxisome Proliferator-Activated Receptors). These receptors are involved in regulating glucose homeostasis, lipid metabolism, and inflammation, making m-ethoxycinnamic acid a potential candidate for developing treatments related to metabolic syndrome.

In conclusion, m-Ethoxycinnamic Acid (CAS No. 188545-72-4) is a multifaceted compound with significant implications in pharmaceuticals, cosmetics, and synthetic chemistry. Its unique structural features enable diverse applications, from anti-inflammatory drugs to skincare products and metabolic regulators. As research continues to uncover new therapeutic potentials, this compound is poised to play an increasingly important role in addressing global health challenges.

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