Methyl 4-hydroxycinnamate

Base Information

• Chemical Name: Methyl 4-hydroxycinnamate
• CAS No.: 19367-38-5
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.188
• European Community (EC) Number: 223-531-1,802-167-2
• NSC Number: 154578
• Nikkaji Number: J45.653E,J717.835B
• Wikidata: Q72491286
• Pharos Ligand ID: 8YRC691XC4MK
• Metabolomics Workbench ID: 70617
• ChEMBL ID: CHEMBL146816
• Mol file: 19367-38-5.mol

Synonyms:4-coumaric acid methyl ester;4-coumaric acid methyl ester, (E)-isomer;para-coumaric acid methyl ester

Chemical Property of Methyl 4-hydroxycinnamate

Chemical Property:

• Appearance/Colour: Off-white to pale orange solid
• Melting Point: 138-140 °C
• Boiling Point: 306.6 °C at 760 mmHg
• PKA: 8.82±0.13(Predicted)
• Flash Point: 132.8 °C
• PSA: 46.53000
• Density: 1.197 g/cm³
• LogP: 1.57840
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• 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:

99% ^*data from raw suppliers

Methyl 4-hydroxy cinnamate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C=CC1=CC=C(C=C1)O
• Isomeric SMILES: COC(=O)/C=C/C1=CC=C(C=C1)O
• Uses: Cinnamic acid derivative used in structure-antifungal activity relationship study against Aspergillus flavus, Aspergillus terreus, and Aspergillus niger. An antifungal agent. Methyl 4-hydroxycinnamate is an antifungal agent,it is used in structure-antifungal activity relationship study against Aspergillus flavus, Aspergillus terreus, and Aspergillus niger.

Technology Process of Methyl 4-hydroxycinnamate

There total 34 articles about Methyl 4-hydroxycinnamate 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 4-acetoxycinnamate (55226-78-3) → methyl p-hydroxycinnamate (3943-97-3,19367-38-5,61240-27-5)

Guidance literature:

With phosphate buffer; In diethyl ether; for 6h; Ambient temperature; pig liver acetone powder;

DOI:10.1080/00397919408011496

Reference yield: 99.0%

4-hydroxybenzenediazonium tetrafluoroborate + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl p-hydroxycinnamate (3943-97-3,19367-38-5,61240-27-5)

Guidance literature:

With sodium acetate; palladium diacetate; In methanol; at 20 ℃; for 12h; Reagent/catalyst; Solvent;

Reference yield: 98.0%

para-coumaric acid (7400-08-0,50940-26-6) + trimethyl orthoformate (149-73-5) → methyl p-hydroxycinnamate (3943-97-3,19367-38-5,61240-27-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 24h; Reflux;

DOI:10.1002/pola.26918

upstream raw materials:

methanol

p-Coumaric Acid

4-hydroxyphenylacryloyl chloride

maleic acid

Downstream raw materials:

3-amino-3-(4-hydroxyphenyl)propionic acid

(E)-p-coumaric amide

(E)-3-{4-[3-(4-Chloro-phenoxy)-2-oxo-propoxy]-phenyl}-acrylic acid methyl ester

3-<4'-(2-Methoxycarbonylvinyl)-phenoxy>-1-(4'-chlorphenoxy)-propanol-(2)

Refernces

• 1、 Huang, Wei-Jan,Chen, Ching-Chow,Chao, Shi-We,Lee, Shoei-Sheng,Hsu, Fen-Lin,Lu, Yeh-Lin,Hung, Ming-Fang,Chang, Chung-I. "Synthesis of n-hydroxycinnamides capped with a naturally occurring moiety as inhibitors of histone deacetylase". . p. 598 - 607. Retrieved 2010.
• 2、 Yang, Fan,Zhang, Yangming,Zheng, Rui,Tang, Jie,He, Mingyuan. "Cyclopalladated complexes of tertiary arylamines as highly efficient catalysts using in the Heck reactions". . p. 146 - 148. Retrieved 2002.
• 3、 Sharma, Shivika,Dogra, Priyanka,Chauhan, Ghanshyam S.,Kanwar, Shamsher S.. "Synthesis of alkyl coumarate esters by celite-bound lipase of Bacillus licheniformis SCD11501". . p. 80 - 86. Retrieved 2014.
• 4、 Tang, Yanfeng,Gao, Pengfei,Wang, Miao,Zhu, Jinli,Wan, Xiangjian. "A novel glycopolymeric ultraviolet absorber covering UV-A and UV-B ranges". . p. 22617 - 22620. Retrieved 2014.
• 5、 Ghabdian, Mahdieh,Nasseri, Mohammad Ali,Allahresani, Ali,Motavallizadehkakhky, Alireza. "Pd salen complex@CPGO as a convenient, effective heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions". . p. 1713 - 1728. Retrieved 2018/05/25.
• 6、 Crotti, Ant?nio E. M.,Dias, Herbert J.,Rodrigues, Matheus L.. "Optimization of the reaction conditions for the synthesis of dihydrobenzofuran neolignans". . p. 20 - 28. Retrieved 2020/12/28.