3,4-Dihydroxycinnamic Acid Phenethyl Ester

Base Information

• Chemical Name: 3,4-Dihydroxycinnamic Acid Phenethyl Ester
• CAS No.: 104594-70-9
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.312
• Hs Code.: 29182900
• European Community (EC) Number: 627-151-0
• DSSTox Substance ID: DTXSID8040987
• Wikidata: Q72515103
• Mol file: 104594-70-9.mol

Synonyms:Caffeic acid-phenethyl ester;3,4-Dihydroxycinnamic Acid Phenethyl Ester;MFCD00866470;Spectrum2_000819;Spectrum3_001986;SCHEMBL93649;KBioGR_000280;KBioSS_000280;3-(3,4-Dihydroxyphenyl)-2-propenoic acid 2-phenylethyl ester;SPBio_000717;DTXSID8040987;KBio2_000280;KBio2_002848;KBio2_005416;KBio3_000559;KBio3_000560;KBio3_002996;phenethyl 3,4-dihydroxycinnamate;Bio2_000280;Bio2_000760;HMS3269P17;HMS3373J18;HMS3653C22;Caffeic acid phenethyl ester (CAPE);AKOS028108482;SY032957;FT-0602911;FT-0651900;P2088;Q27165172

Chemical Property of 3,4-Dihydroxycinnamic Acid Phenethyl Ester

Chemical Property:

• Appearance/Colour: Colorless transparent liquid
• Vapor Pressure: 1.45E-10mmHg at 25°C
• Melting Point: 127-129℃
• Refractive Index: 1.645
• Boiling Point: 498.6 °C at 760 mmHg
• PKA: 8.46±0.20(Predicted)
• Flash Point: 185.1 °C
• PSA: 66.76000
• Density: 1.266 g/cm³
• LogP: 2.89690
• Storage Temp.: Store at 0°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in ethyl acetate at 50mg/ml. Soluble in DMSO and ethanol
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 284.10485899
• Heavy Atom Count: 21
• Complexity: 347

Purity/Quality:

99.8% ^*data from raw suppliers

Caffeic Acid, Phenethyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-38-37-36
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCOC(=O)C=CC2=CC(=C(C=C2)O)O
• Description: Phenylethyl caffeate is one of the allergens of propolis (bee glue); also contained in poplar-bud secretions.
• Uses: Phenylethyl 3,4-dihydroxycinnamate is a potent and specific inhibitor of nuclear transcription factor, NF-κB, activation. It has been shown to significantly suppress the lipoxygenase pathway of arachidonic acid metabolism during inflammation. It inhibits HIV-1 integrase and also inhibits proliferation of transformed cells. It induces apoptosis in transformed fibroblasts, and interferes with EGF signal transduction affecting both protein kinase C and ornithine decarboxylase activity. antineoplastic, antiinflammatory, immunomodulator, NFkB blocker Cytotoxic agent against cancer cell lines. Inhibitor of ornithine decarboxylase and protein tyrosine kinase. Found to be a specific inhibitor of the nuclear transcription factor, NF-kB. It has also been shown to significantly suppress the lipoxygenase pathway of arachidonic acid metabolism during inflammation.

Technology Process of 3,4-Dihydroxycinnamic Acid Phenethyl Ester

There total 14 articles about 3,4-Dihydroxycinnamic Acid Phenethyl Ester 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: 82.6%

3,4-dihydroxybenzaldehyde (139-85-5) + malonic acid monophenethyl ester (848598-50-5) → Caffeic acid phenethyl ester (104594-70-9,115610-29-2,132336-00-6)

Guidance literature:

With piperidine; pyridine; at 20 ℃; for 16h;

Reference yield: 75.0%

(E)-4-(3-oxo-3-phenethoxyprop-1-enyl)-1,2-phenylene diacetate (118971-54-3) → Caffeic acid phenethyl ester (104594-70-9,115610-29-2,132336-00-6)

Guidance literature:

With pyrrolidine; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1016/j.ejmech.2014.01.049

Reference yield: 70.0%

caffeic acid (331-39-5,501-16-6) + 1-phenyl-2-bromoethane (103-63-9) → Caffeic acid phenethyl ester (104594-70-9,115610-29-2,132336-00-6)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; at 20 ℃; for 52h;

DOI:10.1248/cpb.49.236

upstream raw materials:

2-phenylethanol

caffeic acid

dicyclohexyl-carbodiimide

1-phenyl-2-bromoethane

Refernces

• 1、 Choi, Wonbeen,Villegas, Valente,Istre, Hannah,Heppler, Ben,Gonzalez, Niki,Brusman, Nicole,Snider, Lindsey,Hogle, Emily,Tucker, Janelle,O?ate, Alma,O?ate, Sandra,Ma, Lili,Paula, Stefan. "Synthesis and characterization of CAPE derivatives as xanthine oxidase inhibitors with radical scavenging properties". . p. 686 - 695. Retrieved 2019.
• 2、 Gie?el, Josephine M.,Loesche, Anne,Csuk, René. "Caffeic acid phenethyl ester (CAPE)-derivatives act as selective inhibitors of acetylcholinesterase". . p. 259 - 268. Retrieved 2019/06/05.
• 3、 Pagoni, Aikaterini,Daliani, Theohari,Macegoniuk, Katarzyna,Vassiliou, Stamatia,Berlicki, ?ukasz. "Catechol-based inhibitors of bacterial urease". supporting information. p. 1085 - 1089. Retrieved 2019/03/07.