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• Solvents and Organic Chemicals Organic Compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids
• Solvents and Organic Chemicals Organic Compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Hydroxycinnamic acids

2-Propenoic acid, 3-(2-hydroxy-4-methoxyphenyl)-, ethyl ester, (E)- CAS No. 139386-27-9: A Comprehensive Overview

The compound 2-Propenoic acid, 3-(2-hydroxy-4-methoxyphenyl)-, ethyl ester, (E), identified by its CAS number 139386-27-9, is a specialized organic molecule with significant applications in the field of pharmaceutical research and chemical synthesis. This compound belongs to the class of esters derived from cinnamic acid, characterized by its unique structural features that include a phenolic hydroxyl group and a methoxy substituent. The (E) configuration indicates the stereochemical arrangement of the double bond in the molecule, which plays a crucial role in its chemical reactivity and biological interactions.

Recent advancements in medicinal chemistry have highlighted the importance of cinnamoyl esters in drug development due to their versatile pharmacological properties. The presence of both hydroxyl and methoxy groups in 2-Propenoic acid, 3-(2-hydroxy-4-methoxyphenyl)-, ethyl ester, (E) enhances its potential as a bioactive scaffold. Studies have demonstrated that such structural motifs can modulate various biological pathways, making them valuable candidates for therapeutic intervention.

In particular, the phenolic hydroxyl group contributes to the compound's ability to engage in hydrogen bonding interactions, which is a key factor in drug-receptor binding affinity. Additionally, the methoxy group can influence electronic distribution across the molecule, affecting its metabolic stability and bioavailability. These features make 2-Propenoic acid, 3-(2-hydroxy-4-methoxyphenyl)-, ethyl ester, (E) an attractive intermediate for synthesizing more complex pharmacophores.

Current research in synthetic organic chemistry has focused on optimizing the synthesis of this compound to improve yield and purity. One notable approach involves palladium-catalyzed cross-coupling reactions, which enable efficient construction of the cinnamoyl ester core. Such methodologies align with green chemistry principles by minimizing waste and reducing reliance on hazardous reagents. The development of scalable synthetic routes is essential for integrating 2-Propenoic acid, 3-(2-hydroxy-4-methoxyphenyl)-, ethyl ester, (E) into industrial processes for pharmaceutical manufacturing.

Beyond its synthetic utility, 2-Propenoic acid, 3-(2-hydroxy-4-methoxyphenyl)-, ethyl ester, (E) has shown promise in preclinical studies as a potential modulator of inflammatory pathways. The phenolic moiety can interact with enzymes such as lipoxygenases and cyclooxygenases, which are central to inflammatory responses. Preliminary data suggest that derivatives of this compound may exhibit anti-inflammatory effects without significant immunosuppressive side effects. This aligns with the growing demand for targeted therapies that mitigate inflammation while preserving overall immune function.

The stereochemistry of the (E)-configuration also plays a critical role in determining the biological activity of 2-Propenoic acid, 3-(2-hydroxy-4-methoxyphenyl)-, ethyl ester, (E). Stereoisomers of cinnamoyl esters often exhibit distinct pharmacological profiles due to differences in receptor binding affinity and metabolic fate. Computational modeling studies have been instrumental in predicting how subtle changes in stereochemistry can influence biological activity. These insights are guiding efforts to design more potent and selective analogs for therapeutic use.

In addition to its pharmaceutical applications, 2-Propenoic acid, 3-(2-hydroxy-4-methoxyphenyl)-, ethyl ester, (E) has potential uses in agrochemical research. Its structural framework resembles key intermediates found in natural products with insect-repellent properties. By modifying its chemical composition, researchers aim to develop novel compounds that protect crops without harming beneficial insects or human health. This underscores the broad utility of cinnamoyl esters across multiple domains of applied chemistry.

The regulatory landscape for compounds like 2-Propenoic acid, 3-(2-hydroxy-4-methoxyphenyl)-, ethyl ester, (E) is evolving to accommodate advancements in synthetic biology and drug discovery technologies. Regulatory agencies are increasingly emphasizing safety and sustainability in chemical manufacturing processes. Companies developing this compound must navigate stringent guidelines regarding production scalability and environmental impact while ensuring compliance with international trade regulations.

Future directions in research may explore novel derivatives of 2-Propenoic acid, 3-(2-hydroxy-4-methoxyphenyl)-, ethyl ester, (E) through combinatorial chemistry and high-throughput screening techniques. These approaches allow for rapid exploration of large chemical libraries to identify bioactive molecules with optimized properties. The integration of artificial intelligence into drug discovery workflows is also accelerating the identification of promising candidates for further development.

In conclusion,CAS No.139386-27-9 represents a structurally intriguing compound with significant potential across pharmaceuticals and agrochemicals. Its unique combination of functional groups and stereochemical configuration makes it a valuable building block for synthetic chemists and biologists alike. As research continues to uncover new applications for this molecule,its importance is likely to grow within both academic and industrial settings.

• 50636-22-1(2-Propenoic acid,3-(2-ethoxyphenyl)-, ethyl ester)
• 154424-13-2(Methyl 3-(2,6-dimethoxyphenyl)prop-2-enoate)
• 24393-63-3(ethyl (2E)-3-(2,4-dimethoxyphenyl)prop-2-enoate)
• 24393-54-2(Ethyl (E)-3-(2-Methoxyphenyl)prop-2-enoate)
• 33877-05-3(2-Propenoic acid,3-(2-methoxyphenyl)-, ethyl ester)
• 107274-42-0(2-Propenoic acid, 3-(2-methoxy-5-methylphenyl)-, ethyl ester)
• 67827-53-6(Ethyl 2,4,6-Trimethoxycinnamate)
• 86867-64-3(Ethyl 3-(2-phenoxyphenyl)prop-2-enoate)
• 847646-83-7(methyl (2E)-3-(2,4,6-trimethoxyphenyl)prop-2-enoate)
• 477779-96-7