Phenylethyl 3-methylcaffeate

Base Information

• Chemical Name: Phenylethyl 3-methylcaffeate
• CAS No.: 71835-85-3
• Molecular Formula: C₁₈H₁₈O₄
• Molecular Weight: 298.339
• NSC Number: 671193,666255
• UNII: B49B43355J
• DSSTox Substance ID: DTXSID8021143
• Nikkaji Number: J549.663B,J655.985I
• Wikidata: Q27464606
• Metabolomics Workbench ID: 134065
• ChEMBL ID: CHEMBL442022
• Mol file: 71835-85-3.mol

Synonyms:phenethyl ferulate

Chemical Property of Phenylethyl 3-methylcaffeate

Chemical Property:

• Vapor Pressure: 1.23E-09mmHg at 25°C
• Melting Point: 80-81℃
• Boiling Point: 474.7°C at 760 mmHg
• Flash Point: 171.6°C
• PSA: 55.76000
• Density: 1.193g/cm³
• LogP: 3.11930
• Solubility.: DMSO, Ethanol, Ethyl Acetate
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 298.12050905
• Heavy Atom Count: 22
• Complexity: 360

Purity/Quality:

≥98% ^*data from raw suppliers

Caffeic Acid, 3-Methyl Phenethyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)OCCC2=CC=CC=C2)O
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)OCCC2=CC=CC=C2)O
• Uses: It has chemopreventive properties against chemically induced colon carcinogenesis. It enhances apoptosis in azoxymethane induced colon tumors It has chemopreventive properties against chemically induced colon carcinogenesis. It enhances apoptosis in azoxymethane induced colon tumors.

Technology Process of Phenylethyl 3-methylcaffeate

There total 9 articles about Phenylethyl 3-methylcaffeate 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: 78.0%

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + 1-phenyl-2-bromoethane (103-63-9) → 2-phenylethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (132335-98-9,71835-85-3)

Guidance literature:

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid; With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium carbonate; for 0.5h;

1-phenyl-2-bromoethane; With potassium iodide; at 20 ℃; for 48h;

DOI:10.1016/j.bmcl.2019.02.032

Reference yield: 70.0%

3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + 1-phenyl-2-bromoethane (103-63-9) → 3-(4-hydroxy-3-methoxyphenyl)acrylic acid phenethyl ester (71835-85-3)

Guidance literature:

3-(4-hydroxy-3-methoxyphenyl)acrylic acid; With 1,3-dimethyl-2-imidazolidinone; sodium carbonate; for 0.5h;

1-phenyl-2-bromoethane; With potassium iodide; at 50 - 60 ℃;

DOI:10.14233/ajchem.2014.15974

Reference yield: 67.0%

2-phenylethyl (E)-4-ethyloxycarbonyloxy-3-methoxycinnamate → 2-phenylethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (132335-98-9,71835-85-3)

Guidance literature:

With piperidine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.ejmech.2017.02.054

upstream raw materials:

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

2-phenylethanol

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

1-phenyl-2-bromoethane

Refernces

• 1、 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.
• 2、 Sonar, Vijay P.,Corona, Angela,Distinto, Simona,Maccioni, Elias,Meleddu, Rita,Fois, Benedetta,Floris, Costantino,Malpure, Nilesh V.,Alcaro, Stefano,Tramontano, Enzo,Cottiglia, Filippo. "Natural product-inspired esters and amides of ferulic and caffeic acid as dual inhibitors of HIV-1 reverse transcriptase". . p. 248 - 260. Retrieved 2017/03/09.