3,4-Dimethoxycinnamic acid

Base Information

• Chemical Name: 3,4-Dimethoxycinnamic acid
• CAS No.: 14737-89-4
• Molecular Formula: C11H12O4
• Molecular Weight: 208.214
• Hs Code.: 2918999090
• European Community (EC) Number: 219-025-5,238-801-4
• NSC Number: 43569,4323
• UNII: BVZ841PVJL
• DSSTox Substance ID: DTXSID501016475
• Nikkaji Number: J227.171K,J208.407D
• Wikipedia: 3,4-Dimethoxycinnamic_acid
• Wikidata: Q15410159
• Metabolomics Workbench ID: 46482
• ChEMBL ID: CHEMBL320295
• Mol file: 14737-89-4.mol

Synonyms:3,4-dimethoxycinnamic acid;3-(3,4-dimethoxyphenyl)propenoic acid;3-(3,4-dimethoxyphenyl)propenoic acid, (E)-isomer

Chemical Property of 3,4-Dimethoxycinnamic acid

Chemical Property:

• Melting Point: 181-183 °C(lit.)
• Boiling Point: 367.4 °C at 760 mmHg
• PKA: 4.53±0.10(Predicted)
• Flash Point: 144 °C
• PSA: 55.76000
• Density: 1.203 g/cm³
• LogP: 1.80160
• 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% ^*data from raw suppliers

trans 3- ^*data from reagent suppliers

Safty Information:

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

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

Technology Process of 3,4-Dimethoxycinnamic acid

There total 38 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: 97.0%

carbon monoxide (201230-82-2) + (E)-1-bromo-2-(3,4-dimethoxyphenyl)ethene (69731-27-7) → 3,4-dimethoxy-trans-cinnamic acid (14737-89-4)

Guidance literature:

With sodium hydroxide; cetyltrimethylammonim bromide; nickel cyanide; In toluene; at 95 ℃; for 1.5h; under 735.5 Torr;

DOI:10.1016/S0040-4039(00)99078-6

Reference yield: 94.0%

caffeic acid (331-39-5,501-16-6) + dimethyl sulfate (77-78-1) → 3,4-dimethoxy-trans-cinnamic acid (14737-89-4)

Guidance literature:

caffeic acid; With sodium hydroxide; In water; pH=13;

dimethyl sulfate; In water; at 20 ℃; for 10h; pH=> 10;

With hydrogenchloride; In water; pH=2;

DOI:10.1021/acs.jmedchem.0c01143

Reference yield: 94.0%

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + dimethyl sulfate (77-78-1) → 3,4-dimethoxy-trans-cinnamic acid (14737-89-4)

Guidance literature:

With sodium hydroxide; at 20 ℃; Inert atmosphere; Reflux;

DOI:10.1002/anie.201508500

upstream raw materials:

malonic acid

3,4-dimethoxy-benzaldehyde

diazomethane

caffeic acid

Downstream raw materials:

3,3-bis-(3,4-dimethoxyphenyl)propionic acid

ethyl (E)-3,4-dimethoxycinnamate

(E)-3,4-dimethoxycinnamic chloride

3,4-methoxycinnamic acid

Refernces

• 1、 Zhu, Hui,Wang, Zi-Zhen,Qi, Bing,Huang, Tao,Zhu, Hai-Liang. "Synthesis, structure, and biological evaluation of three Cu(II) and Ni(II) (E)-3-(3,4-dimethoxyphenyl)acrylate complexes with organic diamines as potential urease inhibitors". . p. 2980 - 2991. Retrieved 2013.
• 2、 Maki,Okawa,Matsui,Hirano,Niwa. "Hydrogenolysis-free hydrogenation by Pd black powder catalyst". . p. 1590 - 1592. Retrieved 2001.
• 3、 Gayam, Venkatareddy,Ravi, Subban. "Cinnamoylated chloroquine analogues: A new structural class of antimalarial agents". . p. 382 - 391. Retrieved 2017.
• 4、 Calis, Ihsan,Gross, Gian-Andrea,Sticher, Otto. "PHENYLPROPANOID GLYCOSIDES ISOLATED FROM SCROPHULARIA SCOPOLI". . p. 2057 - 2062. Retrieved 1987.
• 5、 Pagoni, Aikaterini,Grabowiecka, Agnieszka,Tabor, Wojciech,Mucha, Artur,Vassiliou, Stamatia,Berlicki, ?ukasz. "Covalent Inhibition of Bacterial Urease by Bifunctional Catechol-Based Phosphonates and Phosphinates". supporting information. p. 404 - 416. Retrieved 2021/01/13.