Cas no 69573-60-0 (2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E)-)

2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E)-, is a catechol-based acrylate ester with a long hydrophobic alkyl chain. This compound combines the reactive vinyl group of acrylic acid with the antioxidant properties of the 3,4-dihydroxyphenyl (catechol) moiety, making it suitable for applications requiring polymerization and oxidative stability. The octadecyl ester group enhances lipophilicity, improving compatibility with nonpolar matrices. Its (2E)-configuration ensures structural specificity, which may influence reactivity and material properties. Potential uses include functional coatings, adhesives, or antioxidant additives where controlled polymerization and radical scavenging are desired. The compound's dual functionality offers a balance between processability and performance in specialized formulations.
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E)- structure
69573-60-0 structure
Product Name:2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E)-
CAS No:69573-60-0
MF:C27H44O4
MW:432.635869026184
CID:391628
PubChem ID:5320237
Update Time:2025-05-21

2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E)- Chemical and Physical Properties

Names and Identifiers

    • 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E)-
    • Octadecyl caffeate
    • octadecyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
    • Caffeic acid n-octadecyl ester
    • [ "" ]
    • 69573-60-0
    • AKOS025287875
    • UNII-458UK7GX7M
    • 458UK7GX7M
    • trans-Caffeic acid stearyl ester
    • CS-0023393
    • FS-8770
    • HY-N3159
    • BDBM50479621
    • n-octadecyl ester
    • Octadecylcaffeate
    • 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (E)-; trans-Caffeic acid stearyl ester
    • SCHEMBL883450
    • CHEMBL471797
    • 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (E)-
    • octadecyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
    • n-octadecyl caffeate
    • OCTADECYL (2E)-3-(3,4-DIHYDROXYPHENYL)PROP-2-ENOATE
    • DA-76376
    • Octadecyl (2E)-3-(3,4-dihydroxyphenyl)acrylate
    • Inchi: 1S/C27H44O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22-31-27(30)21-19-24-18-20-25(28)26(29)23-24/h18-21,23,28-29H,2-17,22H2,1H3/b21-19+
    • InChI Key: QYVZEPLDLPYECM-XUTLUUPISA-N
    • SMILES: O(C(/C=C/C1C=CC(=C(C=1)O)O)=O)CCCCCCCCCCCCCCCCCC

Computed Properties

  • Exact Mass: 432.32400
  • Monoisotopic Mass: 432.32395988g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 31
  • Rotatable Bond Count: 20
  • Complexity: 449
  • 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: 11.1
  • Topological Polar Surface Area: 66.8?2

Experimental Properties

  • Color/Form: Powder
  • Density: 1.011±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 110-112 oC (chloroform )
  • Boiling Point: 560.9±40.0 °C at 760 mmHg
  • Flash Point: 175.5±20.8 °C
  • Solubility: Insuluble (2.4E-5 g/L) (25 oC),
  • PSA: 66.76000
  • LogP: 7.91570
  • Vapor Pressure: 0.0±1.6 mmHg at 25°C

2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E)- Security Information

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Additional information on 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E)-

2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E): A Comprehensive Overview of its Chemical Properties and Emerging Applications

2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E) (CAS No. 69573-60-0) is a specialized organic compound that has garnered significant attention in the field of chemical and pharmaceutical research. This compound, characterized by its unique molecular structure and functional groups, exhibits a range of properties that make it valuable in various applications. The octadecyl ester moiety contributes to its hydrophobicity, while the presence of 3-(3,4-dihydroxyphenyl) suggests potential bioactivity and interaction with biological systems.

The chemical structure of 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E) consists of an unsaturated carboxylic acid backbone substituted with an octadecyl group at one end and a phenolic ring with hydroxyl groups at the other. This configuration imparts both lipophilicity and the ability to engage in hydrogen bonding interactions. Such structural features are often exploited in the development of drug delivery systems, where the compound can serve as a lipid-based carrier or an intermediate in synthetic pathways.

In recent years, there has been growing interest in the potential applications of this compound in pharmaceutical research. The 3-(3,4-dihydroxyphenyl) group is particularly noteworthy due to its resemblance to natural products such as flavonoids and polyphenols, which are known for their antioxidant and anti-inflammatory properties. Preliminary studies have suggested that derivatives of this compound may exhibit similar bioactivities, making it a promising candidate for further investigation in drug discovery.

One of the most intriguing aspects of 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E) is its potential role in nanomedicine. The combination of hydrophobic and hydrophilic regions within its structure allows it to self-assemble into micelles or liposomes when dissolved in appropriate solvents. These nanostructures are highly effective for drug encapsulation and targeted delivery to specific tissues or cells. Recent advancements in nanotechnology have leveraged this property to develop novel formulations for poorly soluble drugs or for enhancing the bioavailability of therapeutic agents.

The octadecyl ester moiety also makes this compound a valuable intermediate in organic synthesis. It can be easily modified through various chemical reactions such as hydrolysis or transesterification to produce other derivatives with tailored properties. For instance, replacing the ester group with a carboxylic acid or amide function can alter its solubility and reactivity. Such modifications are crucial in pharmaceutical development where precise control over molecular structure is essential for optimizing drug efficacy and safety.

Another area where 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E) shows promise is in materials science. Its unique chemical composition allows it to act as a surfactant or plasticizer in polymer formulations. By incorporating this compound into polymeric matrices, researchers have been able to improve material properties such as flexibility and biodegradability. These advancements are particularly relevant in the development of biodegradable implants or wound dressings where controlled degradation rates are critical.

The biological activity of 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, octadecyl ester, (2E) has also been explored in the context of enzyme inhibition and receptor binding studies. The phenolic ring with hydroxyl groups can interact with enzymes such as tyrosine kinases or lipoxygenases through hydrogen bonding networks. Such interactions are often exploited in the design of enzyme inhibitors for therapeutic purposes. Additionally, the lipophilic nature of the octadecyl group facilitates membrane permeability interactions with cellular receptors.

In conclusion,2-Propenoic acid, octadecyl ester, (CAS No. 69573-60-0) is a multifaceted compound with diverse applications across multiple scientific disciplines. Its unique structural features make it suitable for use as a drug delivery agent,nanomedicine, synthetic intermediate,materials science, and biological probe. As research continues to uncover new ways to exploit its properties,this compound is likely to play an increasingly important role in future advancements.

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