Cas no 67827-53-6 (Ethyl 2,4,6-Trimethoxycinnamate)

Ethyl 2,4,6-Trimethoxycinnamate is a synthetic cinnamate ester characterized by its three methoxy substituents on the aromatic ring. This compound exhibits notable stability and UV-absorbing properties, making it useful in photostability studies and as a potential intermediate in organic synthesis. Its structure allows for selective reactivity, particularly in electrophilic aromatic substitution or ester hydrolysis reactions. The methoxy groups enhance solubility in organic solvents, facilitating its use in formulations requiring controlled release or compatibility with hydrophobic matrices. Research suggests applications in pharmaceutical and material science due to its tunable electronic and steric properties. Analytical methods confirm high purity, ensuring reproducibility in experimental or industrial settings.
Ethyl 2,4,6-Trimethoxycinnamate structure
67827-53-6 structure
Product Name:Ethyl 2,4,6-Trimethoxycinnamate
CAS No:67827-53-6
MF:C14H18O5
MW:266.289724826813
CID:508018
PubChem ID:5377733
Update Time:2025-05-21

Ethyl 2,4,6-Trimethoxycinnamate Chemical and Physical Properties

Names and Identifiers

    • 2-Propenoic acid,3-(2,4,6-trimethoxyphenyl)-, ethyl ester
    • 2,4,6-TRIMETHOXYCINNAMIC ACID ETHYL ESTER
    • ethyl (E)-3-(2,4,6-trimethoxyphenyl)prop-2-enoate
    • 2,4,6-trimethoxy-trans-cinnamic acid ethyl ester
    • Ethyl 2,4,6-trimethoxycinnamate
    • Ethyl 2,6-trimethoxycinnamate
    • 67827-53-6
    • 2-Propenoic acid,4,6-trimethoxyphenyl)-, ethyl ester
    • Ethyl (2E)-3-(2,4,6-trimethoxyphenyl)-2-propenoate #
    • 2-Propenoic acid, 3-(2,4,6-trimethoxyphenyl)-, ethyl ester
    • NSC151977
    • (E)-ethyl 3-(2,4,6-trimethoxyphenyl)acrylate
    • NGOZXDZLACOEPS-VOTSOKGWSA-N
    • NSC 151977
    • NSC-151977
    • SCHEMBL1881290
    • DTXSID1070642
    • Ethyl 2,4,6-Trimethoxycinnamate
    • Inchi: 1S/C14H18O5/c1-5-19-14(15)7-6-11-12(17-3)8-10(16-2)9-13(11)18-4/h6-9H,5H2,1-4H3/b7-6+
    • InChI Key: NGOZXDZLACOEPS-VOTSOKGWSA-N
    • SMILES: O(C)C1C=C(C=C(C=1/C=C/C(=O)OCC)OC)OC

Computed Properties

  • Exact Mass: 266.11500
  • Monoisotopic Mass: 266.11542367g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 7
  • Complexity: 288
  • 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: 2.5
  • Topological Polar Surface Area: 54?2

Experimental Properties

  • PSA: 53.99000
  • LogP: 2.28870

Ethyl 2,4,6-Trimethoxycinnamate Pricemore >>

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Ethyl 2,4,6-Trimethoxycinnamate Related Literature

Additional information on Ethyl 2,4,6-Trimethoxycinnamate

Research Brief on Ethyl 2,4,6-Trimethoxycinnamate (CAS: 67827-53-6): Recent Advances and Applications in Chemical Biology and Medicine

Ethyl 2,4,6-Trimethoxycinnamate (CAS: 67827-53-6) is a synthetic cinnamate derivative that has garnered significant attention in the fields of chemical biology and medicinal chemistry due to its diverse pharmacological properties. Recent studies have explored its potential as an anti-inflammatory, antioxidant, and anticancer agent, with promising results in both in vitro and in vivo models. This research brief synthesizes the latest findings on this compound, highlighting its mechanisms of action, therapeutic applications, and future research directions.

One of the most notable advancements in the study of Ethyl 2,4,6-Trimethoxycinnamate is its role in modulating inflammatory pathways. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that this compound effectively inhibits the NF-κB signaling pathway, a key regulator of inflammation. The study utilized lipopolysaccharide (LPS)-induced RAW 264.7 macrophages as a model system and found that Ethyl 2,4,6-Trimethoxycinnamate significantly reduced the production of pro-inflammatory cytokines such as TNF-α and IL-6. These findings suggest its potential as a lead compound for developing novel anti-inflammatory drugs.

In addition to its anti-inflammatory properties, Ethyl 2,4,6-Trimethoxycinnamate has shown remarkable antioxidant activity. Research published in Free Radical Biology and Medicine in 2022 revealed that the compound scavenges reactive oxygen species (ROS) and enhances the activity of endogenous antioxidant enzymes, such as superoxide dismutase (SOD) and catalase (CAT). These effects were observed in a hydrogen peroxide (H2O2)-induced oxidative stress model in human keratinocytes, indicating its potential for protecting against oxidative damage in skin-related disorders.

The anticancer potential of Ethyl 2,4,6-Trimethoxycinnamate has also been a focal point of recent investigations. A 2023 study in Bioorganic & Medicinal Chemistry Letters reported that the compound induces apoptosis in human breast cancer cells (MCF-7) by activating the intrinsic mitochondrial pathway. Mechanistic studies revealed that Ethyl 2,4,6-Trimethoxycinnamate upregulates pro-apoptotic proteins like Bax and downregulates anti-apoptotic proteins like Bcl-2, leading to caspase-3 activation and subsequent cell death. These results position the compound as a promising candidate for further development in oncology.

Despite these promising findings, challenges remain in the clinical translation of Ethyl 2,4,6-Trimethoxycinnamate. Pharmacokinetic studies, as reported in a 2023 issue of European Journal of Pharmaceutical Sciences, indicate that the compound exhibits low oral bioavailability due to poor solubility and rapid metabolism. To address this, researchers are exploring formulation strategies such as nanoemulsions and solid dispersions to enhance its delivery and efficacy. These efforts are critical for advancing the compound from bench to bedside.

In conclusion, Ethyl 2,4,6-Trimethoxycinnamate (CAS: 67827-53-6) represents a multifaceted compound with significant therapeutic potential. Its anti-inflammatory, antioxidant, and anticancer properties, as evidenced by recent studies, make it a valuable subject for further research. Future studies should focus on optimizing its pharmacokinetic profile and elucidating its mechanisms of action in greater detail. With continued investigation, this compound may pave the way for new treatments in a range of diseases.

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