Methyl ferulate

Base Information

• Chemical Name: Methyl ferulate
• CAS No.: 22329-76-6
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.214
• European Community (EC) Number: 606-986-4
• NSC Number: 74548
• UNII: Y98BUA66RX
• Nikkaji Number: J62.860C,J101.772A
• Wikidata: Q27135838
• Metabolomics Workbench ID: 70626
• ChEMBL ID: CHEMBL32969
• Mol file: 22329-76-6.mol

Synonyms:methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)acrylate;methyl ferulate

Chemical Property of Methyl ferulate

Chemical Property:

• Melting Point: 63-65 °C(lit.)
• Boiling Point: 164-166 °C0.5 mm Hg(lit.)
• PSA: 55.76000
• LogP: 1.58700
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 208.07355886
• Heavy Atom Count: 15
• Complexity: 237

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methylferulate 95+% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)OC)O
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)OC)O
• Uses: Methyl (2E)-3-(4-Hydroxy-3-methoxyphenyl)acrylate used in method for preparation of Photoaligning polymer materials and compounds.

Technology Process of Methyl ferulate

There total 21 articles about Methyl ferulate 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%

methanol (67-56-1) + 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) → methyl ferulate (22329-76-6,34298-89-0,2309-07-1)

Guidance literature:

at 50 ℃; for 12h;

Reference yield: 100.0%

3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + acetyl chloride (75-36-5) → methyl ferulate (22329-76-6,34298-89-0,2309-07-1)

Guidance literature:

In methanol; for 1h; Inert atmosphere; Reflux;

DOI:10.1039/c5gc01334h

Reference yield: 98.0%

3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + trimethyl orthoformate (149-73-5) → methyl ferulate (22329-76-6,34298-89-0,2309-07-1)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 24h; Reflux;

DOI:10.1002/pola.26918

upstream raw materials:

methanol

3-O-feruloylquinic acid methyl ester

3-O-caffeoylquinic acid methyl ester

3,6-diferuloylsucrose

Downstream raw materials:

C₂₄H₂₈O₁₃

methyl (E)-3-[2-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]propen-2-enoate

C₂₄H₂₈O₁₀

4-hydroxy-3-methoxy butyl cinnamate

Refernces

• 1、 Tanaka et al.. "". . p. 95. Retrieved 1971.
• 2、 Crotti, Ant?nio E. M.,Dias, Herbert J.,Rodrigues, Matheus L.. "Optimization of the reaction conditions for the synthesis of dihydrobenzofuran neolignans". . p. 20 - 28. Retrieved 2020/12/28.
• 3、 Gan, Xiuhai,Wang, Zhengxing,Hu, Deyu. "Synthesis of Novel Antiviral Ferulic Acid-Eugenol and Isoeugenol Hybrids Using Various Link Reactions". . p. 13724 - 13733. Retrieved 2021/11/23.