3,4-Dimethoxycinnamic acid

Base Information

• Chemical Name: 3,4-Dimethoxycinnamic acid
• CAS No.: 2316-26-9
• Molecular Formula: C11H12O4
• Molecular Weight: 208.214
• Hs Code.: 2916.39 DERIVATION
• UNII: 1EUC2RA0WK
• Wikidata: Q27887071
• Mol file: 2316-26-9.mol

Synonyms:3,4-Dimethoxyphenyl-2-propenoic acid;2-Propenoic acid, 3-(3,4-dimethoxyphenyl)-;Cinnamic acid, 3,4-dimethoxy-;2-Propenoic acid, 3- (3,4-dimethoxyphenyl)-;3-(3,4-Dimethoxyphenyl)propenoic acid;Caffeic acid dimethyl ether;Cinnamic acid, 3,4-dimethoxy- (8CI);

Chemical Property of 3,4-Dimethoxycinnamic acid

Chemical Property:

• Appearance/Colour: Slightly yellow to light beige powder
• Vapor Pressure: 4.8E-06mmHg at 25°C
• Melting Point: 181-183 °C(lit.)
• Refractive Index: 1.4389 (estimate)
• Boiling Point: 367.4oCat 760 mmHg
• PKA: 4.53±0.10(Predicted)
• Flash Point: 144oC
• PSA: 55.76000
• Density: 1.203 g/cm³
• LogP: 1.80160
• Storage Temp.: -20°C
• Solubility.: Solubility in hot methanol, very faint turbidity. Soluble in dic
• 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:

99% ^*data from raw suppliers

3,4-Dimethoxycinnamic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=CC(=O)O)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C\C(=O)O)OC
• Uses: 3,4-Dimethoxycinnamic Acid is a Cinnamic Acid (C442030) derivative,used in the synthesis of amides and esters through coupling reactions involving carboxylic acids and amines and N-methylation of amides and O-methylation of carboxylic acids.

Technology Process of 3,4-Dimethoxycinnamic acid

There total 28 articles about 3,4-Dimethoxycinnamic acid 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%

methyl 3,4-dimethoxycinnamate (30461-77-9,30461-78-0,5396-64-5) → 3,4-dimethoxycinnamic acid (2316-26-9)

Guidance literature:

methyl 3,4-dimethoxycinnamate; With lithium hydroxide; In water; diethylene glycol; at 90 ℃; for 0.25h; Sonication; Microwave irradiation;

With hydrogenchloride; In water; diethylene glycol;

DOI:10.1080/00397910902738112

Reference yield: 99.0%

malonic acid (141-82-2) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 3,4-dimethoxycinnamic acid (2316-26-9)

Guidance literature:

With piperidine; pyridine; at 115 ℃;

DOI:10.1021/acs.orglett.6b00315

Reference yield: 70.0%

caffeic acid (331-39-5,501-16-6) + methyl iodide (74-88-4) → 3,4-dimethoxycinnamic acid (2316-26-9)

Guidance literature:

caffeic acid; methyl iodide; With potassium carbonate; In acetone; Reflux;

In methanol; at 20 ℃; for 10h; Alkaline conditions;

With hydrogenchloride; In methanol; water; at 20 ℃;

DOI:10.1007/s00044-021-02810-w

upstream raw materials:

piperidine

pyridine

malonic acid

3,4-dimethoxy-benzaldehyde

Downstream raw materials:

3,4-methoxycinnamic acid

C₂₈H₃₆N₂O₆

(E)-3-(3,4-Dimethoxy-phenyl)-acrylic acid 2,3-dimethoxy-phenyl ester

C₃₄H₄₄O₉

Refernces

• 1、 Meng, Zihui,Wang, Hongyi,Wang, Yiyun,Xu, Haojie,Xu, Zhibin,Xue, Min,Zheng, Zhonghui. "Separation and identification of an impurity from the istradefylline intermediate". . p. 14493 - 14499. Retrieved 2020.
• 2、 Birmingham, William R.,Galman, James L.,Parmeggiani, Fabio,Seibt, Lisa,Turner, Nicholas J.. "One-Pot Biocatalytic In Vivo Methylation-Hydroamination of Bioderived Lignin Monomers to Generate a Key Precursor to L-DOPA". . . Retrieved 2022/01/13.
• 3、 Malbari, Khushboo,Saha, Priyanka,Chawla-Sarkar, Mamta,Dutta, Shanta,Rai, Swita,Joshi, Mamata,Kanyalkar, Meena. "In quest of small-molecules as potent non-competitive inhibitors against influenza". . . Retrieved 2021/07/19.