Methyl 4-hydroxy-3-methoxy-cinnamate

Base Information

• Chemical Name: Methyl 4-hydroxy-3-methoxy-cinnamate
• CAS No.: 2309-07-1
• Molecular Formula: C11H12O4
• Molecular Weight: 208.214
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID801347441
• Wikidata: Q104918972
• Mol file: 2309-07-1.mol

Synonyms:SCHEMBL510492;DTXSID801347441;methyl 3-methoxy-4-hydroxycinnamate;methyl 4-hydroxy-3-methoxy-cinnamate;METHYL-4-HYDROXY-3-METHOXYCINNAMATE;FT-0698057;FT-0772817

Chemical Property of Methyl 4-hydroxy-3-methoxy-cinnamate

Chemical Property:

• Vapor Pressure: 5.13E-05mmHg at 25°C
• Melting Point: 62-65 °C
• Refractive Index: 1.574
• Boiling Point: 338.077 °C at 760 mmHg
• PKA: 8.88±0.18(Predicted)
• Flash Point: 130.409 °C
• PSA: 55.76000
• Density: 1.205 g/cm³
• LogP: 1.58700
• Storage Temp.: 2-8°C
• Solubility.: Acetone (Slightly), Chloroform (Slightly), Ethyl Acetate (Sparingly), Methanol (
• Water Solubility.: Slightly soluble in water.
• 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%min ^*data from raw suppliers

Methyl4-Hydroxy-3-methoxycinnamate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)OC)O
• Uses: 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 methyl ester is a lipophilic derivative of ferulic acid, demonstrating increased ability to cross cell membranes. Ferulic acid methyl ester has less antioxidant capacity than ferulic acid in neuronal PC12 cells (IC50 = 74.7 μM for ferulic acid ethyl ester vs. 44.6 μM for ferulic acid, 2,2-diphenyl-1-picrylhydrazyl radical scavenging). Ferulic acid methyl ester, at 10-25 μg/ml, inhibits the release of pro-inflammatory cytokines, blocks the expression of COX-2, and reduces nitric oxide generation from LPS-stimulated macrophages. Ferulic Acid Methyl Ester is a derivative of Ferulic Acid (F308900), used as an antioxidant and food preservative. It has less antioxidant capacity than ferulic acid.

Technology Process of Methyl 4-hydroxy-3-methoxy-cinnamate

There total 85 articles about Methyl 4-hydroxy-3-methoxy-cinnamate 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:

Methyl <5-hydroxy-t-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-c-2-(methoxycarbonyl)-r-1-indanyl>acetate

4-hydroxy-3-methoxybenzoic acid methyl ester

vanillin

methyl 3-[2-methoxy-4-(methoxycarbonylmethoxy)phenyl]acrylate

Refernces

• 1、 Hann. "-". . p. 5049. Retrieved 1930.
• 2、 She, Xuegong,Gu, Wenxin,Wu, Tongxing,Pan, Xinfu. "A convenient synthesis of (±)-3-methoxybenzodioxane-4,9,9'-triol neolignan, and methyl ethers of isoamericanol A and isoamericanin A". . p. 100 - 101. Retrieved 1999.
• 3、 Wallace, Graham,Fry, Stephen C.. "IN VITRO PEROXIDASE-CATALYSED OXIDATION OF FERULIC ASID ESTERS". . p. 1293 - 1300. Retrieved 1995.
• 4、 Kim, Ki Hyun,Kim, Chung Sub,Park, Yong Joo,Moon, Eunjung,Choi, Sang Un,Lee, Jei Hyun,Kim, Sun Yeou,Lee, Kang Ro. "Anti-inflammatory and antitumor phenylpropanoid sucrosides from the seeds of Raphanus sativus". . p. 96 - 99. Retrieved 2014.
• 5、 Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar. "Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites". supporting information. p. 1929 - 1940. Retrieved 2022/02/01.
• 6、 Pongpamorn, Pornkanok,Kiattisewee, Cholpisit,Kittipanukul, Narongyot,Jaroensuk, Juthamas,Trisrivirat, Duangthip,Maenpuen, Somchart,Chaiyen, Pimchai. "Carboxylic Acid Reductase Can Catalyze Ester Synthesis in Aqueous Environments". supporting information. p. 5749 - 5753. Retrieved 2021/02/01.