4-Methoxycinnamic acid

Base Information

• Chemical Name: 4-Methoxycinnamic acid
• CAS No.: 943-89-5
• Molecular Formula: C10H10O3
• Molecular Weight: 178.188
• Hs Code.: 2916399090
• European Community (EC) Number: 212-594-0,213-405-4
• NSC Number: 623437,5303
• UNII: 6G4ML8401A
• DSSTox Substance ID: DTXSID1046059
• Nikkaji Number: J47.704D,J60.989G
• Wikidata: Q63391599
• Metabolomics Workbench ID: 37990
• ChEMBL ID: CHEMBL95770
• Mol file: 943-89-5.mol

Synonyms:4-methoxycinnamate;4-methoxycinnamate, (E)-isomer;4-methoxycinnamate, (Z)-isomer;4-methoxycinnamate, aluminum salt;4-methoxycinnamate, calcium salt;4-methoxycinnamate, magnesium salt;4-methoxycinnamate, potassium salt;4-methoxycinnamate, sodium salt;4-methoxycinnamate, zinc salt;4-methoxycinnamate, zirconium salt;4-methoxycinnamic acid;4-methoxycinnamic acid, (Z)-;E-p-methoxycinnamic acid

Chemical Property of 4-Methoxycinnamic acid

Chemical Property:

• Melting Point: 173.5 °C(lit.)
• Boiling Point: 342.6 °C at 760 mmHg
• PKA: 4.60±0.10(Predicted)
• Flash Point: 138.5 °C
• PSA: 46.53000
• Density: 1.195 g/cm³
• LogP: 1.79300
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Soluble in ethanol, ethyl acetate and other organic solvents.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 178.062994177
• Heavy Atom Count: 13
• Complexity: 190

Purity/Quality:

98% ^*data from raw suppliers

trans-4-Methoxycinnamic Acid >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=CC(=O)O
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C/C(=O)O
• Uses: Esters derived from trans-4-methoxycinnamic acid are effective absorbers of UV radiation. The starting material was trans-4-methoxycinnamic acid and 3,5dimethoxybenzoic acid methyl ester in isolated avenanthramide alkaloids synthsis. trans-4-Methoxycinnamic acid was converted into its acid chloride (yield 98%) with thionyl chloride. Employed in organic synthesis of pharmaceutical intermediates, synthetic anti-adrenergic drugs esmolol, cosmetics ultraviolet absorption.

Technology Process of 4-Methoxycinnamic acid

There total 98 articles about 4-Methoxycinnamic 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: 99.0%

carbon monoxide (201230-82-2) + 4-(2-bromo-vinyl)-anisole (27570-08-7,60592-52-1,6303-59-9) → (E)-3-(4-methoxyphenyl)acrylic acid (943-89-5)

Guidance literature:

With [bmim]PF₆; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In water; at 100 ℃; for 20h; under 15001.2 Torr;

DOI:10.1021/jo052651p

Reference yield: 98.0%

malonic acid (141-82-2) + 4-methoxy-benzaldehyde (123-11-5) → (E)-3-(4-methoxyphenyl)acrylic acid (943-89-5)

Guidance literature:

With ammonium acetate; for 0.05h; Irradiation;

Reference yield: 98.0%

para-iodoanisole (696-62-8) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (E)-3-(4-methoxyphenyl)acrylic acid (943-89-5)

Guidance literature:

With triethylamine; di-(3-methylphenyl)phosphinopolystyrene palladium catalyst; In acetonitrile; at 80 ℃; for 20h;

DOI:10.1002/adsc.200600503

upstream raw materials:

3-(4-methoxy-phenyl)acrylic acid methyl ester

2,3-dibromo-3-(4-methoxy-phenyl)-propionic acid

acetic acid methyl ester

4-methoxy-benzaldehyde

Downstream raw materials:

4-Methoxystyrene

3-(p-methoxyphenyl)-1-propanol

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

(E)-N,N-diethyl-3-(4-methoxyphenyl)propenamide

Refernces

• 1、 Baruch, Yifat,Gopas, Jacob,Kadosh, Yael,Kumar, Rajendran Saravana,Kushmaro, Ariel,Muthuraman, Subramani,Yaniv, Karin. "Quorum sensing and nf-κb inhibition of synthetic coumaperine derivatives from piper nigrum". supporting information. . Retrieved 2021/05/28.
• 2、 Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei. "Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation". supporting information. p. 5905 - 5908. Retrieved 2021/06/18.