Ethyl ferulate

Base Information

• Chemical Name: Ethyl ferulate
• CAS No.: 4046-02-0
• Molecular Formula: C12H14O4
• Molecular Weight: 222.241
• Hs Code.: 29189900
• European Community (EC) Number: 223-745-5
• NSC Number: 14879
• UNII: 5B8915UELW
• Nikkaji Number: J729.906K,J217.860E
• Wikidata: Q27261780
• NCI Thesaurus Code: C83699
• Metabolomics Workbench ID: 130035
• ChEMBL ID: CHEMBL286796
• Mol file: 4046-02-0.mol

Synonyms:ethyl 4-hydroxy-3-methoxycinnamate;ethyl ferulate;ferulic acid, ethyl ester

Chemical Property of Ethyl ferulate

Chemical Property:

• Vapor Pressure: 2.17E-06mmHg at 25°C
• Melting Point: 63-65 °C(lit.)
• Refractive Index: 1.565
• Boiling Point: 382.3 °C at 760 mmHg
• PKA: 8.88±0.18(Predicted)
• Flash Point: 132.5 °C
• PSA: 55.76000
• Density: 1.173 g/cm³
• LogP: 1.97710
• Storage Temp.: Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 222.08920892
• Heavy Atom Count: 16
• Complexity: 249

Purity/Quality:

99% ^*data from raw suppliers

Ferulic acid ethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CC(=C(C=C1)O)OC
• Isomeric SMILES: CCOC(=O)/C=C/C1=CC(=C(C=C1)O)OC
• Description: Ferulic acid is a hydroxycinnamic acid that is abundant in plants and originally derived from giant fennel (F. communis). This naturally-occurring phenolic has antioxidant activities that provide protection against inflammation and cancer. Ferulic acid ethyl ester is a lipophilic derivative of ferulic acid, demonstrating increased ability to cross cell membranes. Ferulic acid ethyl ester has less antioxidant capacity than ferulic acid in neuronal PC12 cells (IC50 = 66.7 μM for ferulic acid ethyl ester vs. 44.6 μM for ferulic acid, 2,2-diphenyl-1-picrylhydrazyl radical scavenging). However, ferulic acid ethyl ester increases the expression of heme oxygenase-1, Hsp70, and Hsp72, providing neuroprotection against amyloid β-peptide. Moreover, ferulic acid ethyl ester (25 μM) completely prevents cytotoxicity induced by ultraviolet B irradiation of normal human epidermal melanocytes, again associated with an induced expression of heme oxygenase-1 and Hsp70.
• Uses: Ferulic acid ethyl ester is an ethyl ester derivative of Ferulic acid (F308900), which is used as an antioxidant and food preservative.

Technology Process of Ethyl ferulate

There total 29 articles about Ethyl 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%

3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + ethanol (64-17-5) → ethyl ferulate (28028-62-8,74257-26-4,4046-02-0)

Guidance literature:

at 50 ℃; for 76h;

Reference yield: 100.0%

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + ethanol (64-17-5) → ethyl 4-hydroxy-3-methoxycinnamate (4046-02-0)

Guidance literature:

With acetyl chloride; at 20 ℃;

DOI:10.1021/acs.jafc.6b02720

Reference yield: 98.0%

hydrogen ethyl malonate (1071-46-1) + vanillin (121-33-5,8014-42-4) → ethyl 4-hydroxy-3-methoxycinnamate (4046-02-0)

Guidance literature:

hydrogen ethyl malonate; vanillin; With piperidine; pyridine; at 100 ℃; for 24h;

With hydrogenchloride; In water; at -10 - 0 ℃; for 24h;

DOI:10.1177/1747519819890821

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

vanillin

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

ethanol

Downstream raw materials:

4-(3,4-dimethoxy-phenacyloxy)-3-methoxy-trans-cinnamic acid ethyl ester

coniferal alcohol

ethyl 3-(4-hydroxy-3-methoxyphenyl)propanoate

ethyl (E)-3-(4-acetoxy-3-methoxyphenyl)-prop-2-enoate

Refernces

• 1、 Rychlicka, Magdalena,Maciejewska, Gabriela,Niezgoda, Natalia,Gliszczyńska, Anna. "Production of feruloylated lysophospholipids via a one-step enzymatic interesterification". . . Retrieved 2020.
• 2、 Bunzel, Mirko,Heuermann, Birgit,Kim, Hoon,Ralph, John. "Peroxidase-catalyzed oligomerization of ferulic acid esters". . p. 10368 - 10375. Retrieved 2008.
• 3、 Sandoval, Georgina,Quintana, Paula G.,Baldessari, Alicia,Ballesteros, Antonio O.,Plou, Francisco J.. "Lipase-catalyzed preparation of mono- and diesters of ferulic acid". . p. 89 - 97. Retrieved 2015.
• 4、 Au, Chi-Ming,Ling, Cho-Hon,Sun, Wenlong,Yu, Wing-Yiu. "Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones". supporting information. p. 3310 - 3314. Retrieved 2021/05/29.
• 5、 Xu, Guangya,Wu, Min,Yao, Zhongquan,Lou, Hongbin,Du, Weihong,Song, Mingwei,He, Yujiao,Dong, Hongbo. "First total syntheses of four natural bioactive glucosides". supporting information. p. 1266 - 1271. Retrieved 2021/02/06.