Ethyl caffeate

Base Information

• Chemical Name: Ethyl caffeate
• CAS No.: 102-37-4
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.214
• Hs Code.: 2918290000
• NSC Number: 619661
• UNII: 76GBB1JU5Y
• DSSTox Substance ID: DTXSID70876375
• Nikkaji Number: J275.522J,J415.776A
• Wikipedia: Ethyl_caffeate
• Wikidata: Q5404446
• Metabolomics Workbench ID: 124285
• ChEMBL ID: CHEMBL17347
• Mol file: 102-37-4.mol

Synonyms:caffeic acid ethyl ester;ethyl caffeate;ethyl trans-caffeate

Chemical Property of Ethyl caffeate

Chemical Property:

• Vapor Pressure: 3.22E-06mmHg at 25°C
• Melting Point: 149.5 °C
• Refractive Index: 1.612
• Boiling Point: 377 °C at 760 mmHg
• PKA: 8.71±0.18(Predicted)
• Flash Point: 148.4 °C
• PSA: 66.76000
• Density: 1.271g/cm³
• LogP: 1.67410
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 208.07355886
• Heavy Atom Count: 15
• Complexity: 237

Purity/Quality:

99% ^*data from raw suppliers

Ethyl caffeate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CC(=C(C=C1)O)O
• Isomeric SMILES: CCOC(=O)/C=C/C1=CC(=C(C=C1)O)O
• Uses: Food antioxidant.

Technology Process of Ethyl caffeate

There total 13 articles about Ethyl caffeate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethanol (64-17-5) + caffeic acid (331-39-5,501-16-6) → ethyl caffeate (66648-50-8,74257-25-3,102-37-4)

Guidance literature:

at 50 ℃; for 48h;

Reference yield: 99.0%

ethanol (64-17-5) + caffeic acid (331-39-5,501-16-6) → ethyl caffeate (74257-25-3,102-37-4,66648-50-8)

Guidance literature:

With hydrogenchloride; at 70 ℃; for 2h;

DOI:10.3390/molecules19067269

Reference yield: 95.0%

ethanol (64-17-5) + caffeic acid (331-39-5,501-16-6) → ethyl caffeate (74257-25-3,102-37-4,66648-50-8)

Guidance literature:

With sulfuric acid; for 6h; Reflux;

DOI:10.1039/c3ob42521e

upstream raw materials:

ethanol

caffeic acid

hydrogen ethyl malonate

3,4-dihydroxybenzaldehyde

Downstream raw materials:

(E)-4-(3-hydroxyprop-1-en-1-yl)benzene-1,2-diol

Methyl caffeate

ethyl 3,4-diacetoxycinnamate

3-(3,4-Diacetoxy-phenyl)-6-((E)-2-ethoxycarbonyl-vinyl)-2,3-dihydro-benzo[1,4]dioxine-2-carboxylic acid ethyl ester

Refernces

• 1、 Andrade, Mafalda,Benfeito, Sofia,Soares, Pedro,Magalh?es e Silva, Diogo,Loureiro, Joana,Borges, Anabela,Borges, Fernanda,Sim?es, Manuel. "Fine-tuning of the hydrophobicity of caffeic acid: studies on the antimicrobial activity against Staphylococcus aureus and Escherichia coli". . p. 53915 - 53925. Retrieved 2015.
• 2、 Freiría-Gándara,Losada-Barreiro,Paiva-Martins,Bravo-Díaz. "Differential Partitioning of Bioantioxidants in Edible Oil-Water and Octanol-Water Systems: Linear Free Energy Relationships". . p. 2999 - 3007. Retrieved 2018.
• 3、 Sardi, Janaína de Cássia Orlandi,Gullo, Fernanda Patrícia,Freires, Irlan Almeida,Pitangui, Nayla de Souza,Segalla, Maicon Petr?nio,Fusco-Almeida, Ana Marisa,Rosalen, Pedro Luiz,Regasini, Luís Octávio,Mendes-Giannini, Maria José Soares. "Synthesis, antifungal activity of caffeic acid derivative esters, and their synergism with fluconazole and nystatin against Candida spp.". . p. 387 - 391. Retrieved 2016.
• 4、 Bhullar, Khushwant S.,Lassalle-Claux, Grégoire,Touaibia, Mohamed,Vasantha Rupasinghe. "Antihypertensive effect of caffeic acid and its analogs through dual renin-angiotensin-aldosterone system inhibition". . p. 125 - 132. Retrieved 2014.
• 5、 Romero, Max,Rojano, Benjamin,Mella-Raipan, Jaime,Pessoa-Mahana, Carlos David,Lissi, Eduardo,Lopez-Alarcon, Camilo. "Antioxidant Capacity of pure compounds and complex mixtures evaluated by the ORAC-pyrogallol red assay in the presence of Triton X-100 micelles". . p. 6152 - 6167. Retrieved 2010.
• 6、 Etzenhouser, Beth,Hansch, Corwin,Kapur, Sanjay,Selassie. "Mechanism of toxicity of esters of caffeic and dihydrocaffeic acids". . p. 199 - 209. Retrieved 2001.
• 7、 Galat. "-". . p. 376. Retrieved 1946.
• 8、 Suárez-Escobedo, Laura,Gotor-Fernández, Vicente. "Solvent role in the lipase-catalysed esterification of cinnamic acid and derivatives. Optimisation of the biotransformation conditions". . . Retrieved 2021/02/05.
• 9、 Bernal, Freddy A.,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.. "Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents". . p. 68 - 78. Retrieved 2019/11/22.