Methyl 4-acetoxy-3-methoxycinnamate

Base Information

• Chemical Name: Methyl 4-acetoxy-3-methoxycinnamate
• CAS No.: 2309-08-2
• Molecular Formula: C13H14O5
• Molecular Weight: 0
• Hs Code.: 2918990090
• NSC Number: 16960
• DSSTox Substance ID: DTXSID50417841
• Nikkaji Number: J1.390.626B,J103.466I
• Wikidata: Q27159267
• Metabolomics Workbench ID: 70625
• Mol file: 2309-08-2.mol

Synonyms:NSC16960;methyl 4-acetoxy-3-methoxycinnamate;bmse010081;Cinnamic acid, methyl ester, acetate;2309-08-2;AC1NS62R;CHEBI:86585;ferulic acid methyl ester acetate;DTXSID50417841;HLCZBCWZTSEZGB-FNORWQNLSA-N;ferulic acid methyl ester monoacetate;NSC-16960;Methyl trans-4-acetoxy-3-methoxycinnamate;3-Methoxy-4-acetoxybenzeneacrylic acid methyl ester;Q27159267;Cinnamic acid, 4-hydroxy-3-methoxy-, methyl ester, acetate;methyl (E)-3-(4-acetoxy-3-methoxy-phenyl)prop-2-enoate;methyl (2E)-3-[4-(acetyloxy)-3-methoxyphenyl]prop-2-enoate;Methyl (2E)-3-[4-(acetyloxy)-3-methoxyphenyl]-2-propenoate #;2-Propenoic acid, 3-[4-(acetyloxy)-3-methoxyphenyl]-, methyl ester

Chemical Property of Methyl 4-acetoxy-3-methoxycinnamate

Chemical Property:

• Vapor Pressure: 5.17E-05mmHg at 25°C
• Boiling Point: 348°C at 760 mmHg
• Flash Point: 152.4°C
• PSA: 61.83000
• Density: 1.18g/cm³
• LogP: 1.80670
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 250.08412354
• Heavy Atom Count: 18
• Complexity: 323

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=C(C=C(C=C1)C=CC(=O)OC)OC
• Isomeric SMILES: CC(=O)OC1=C(C=C(C=C1)/C=C/C(=O)OC)OC

Technology Process of Methyl 4-acetoxy-3-methoxycinnamate

There total 5 articles about Methyl 4-acetoxy-3-methoxycinnamate 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: 99.0%

Isopropenyl acetate (108-22-5) + methyl ferulate (22329-76-6,34298-89-0,2309-07-1) → 4-acetoxy-3-methoxy-cinnamic acid methyl ester (2309-08-2)

Guidance literature:

With iron(III) trifluoromethanesulfonate; at 20 ℃; for 5h; Schlenk technique;

DOI:10.1039/c8gc00037a

Reference yield: 91.0%

methyl ferulate (22329-76-6,34298-89-0,2309-07-1) + acetic anhydride (108-24-7) → 4-acetoxy-3-methoxy-cinnamic acid methyl ester (2309-08-2)

Guidance literature:

With pyridine; In ethyl acetate; at 20 ℃;

DOI:10.1002/cplu.201402181

Reference yield:

3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) → 4-acetoxy-3-methoxy-cinnamic acid methyl ester (2309-08-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / methanol / Reflux

2: pyridine / ethyl acetate / 20 °C

With pyridine; sulfuric acid; In methanol; ethyl acetate;

DOI:10.1002/cplu.201402181

upstream raw materials:

diazomethane

3-(4-acetoxy-3-methoxyphenyl)prop-2-enoic acid

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

methyl ferulate

Downstream raw materials:

3-(4-Acetoxy-3-methoxy-phenyl)-2,3-dibromo-propionic acid methyl ester

4-hydroxy-3-methoxyphenylpropiolic acid

Refernces

• 1、 Juhsz, Lszl,Varga, Gergely,Sztankovics, Andrea,Bke, Ferenc,Docsa, Tibor,Kiss-Szikszai, Attila,Gergely, Pl,Ka, Juraj,Tvaroka, Igor,Somsk, Lszl. "Structure-activity relationships of glycogen phosphorylase inhibitor FR258900 and its analogues: A combined synthetic, enzyme kinetics, and computational study". . p. 1558 - 1568. Retrieved 2015/02/05.