Methyl 4-hydroxycinnamate

Base Information

• Chemical Name: Methyl 4-hydroxycinnamate
• CAS No.: 3943-97-3
• Molecular Formula: C10H10 O3
• Molecular Weight: 178.188
• Hs Code.: 2918290000
• 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: 3943-97-3.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:

• Vapor Pressure: 0.000421mmHg at 25°C
• Melting Point: 144-145oC
• Boiling Point: 306.6°Cat760mmHg
• PKA: 8.82±0.13(Predicted)
• Flash Point: 132.8°C
• PSA: 46.53000
• Density: 1.197g/cm³
• LogP: 1.57840
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: 5.332g/L at 25℃
• 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

3-(4-Hydroxyphenyl)-2-propenoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CC1=CC=C(C=C1)O
• Isomeric SMILES: COC(=O)/C=C/C1=CC=C(C=C1)O
• Description: Methyl 4-hydroxycinnamate is an atifungal agent and a cinnamic acid derivative used in structure-antifungal activity relationship studies against Aspergillus flavus, Aspergillus terreus, and Aspergillus niger.
• Uses: 3-(4-Hydroxyphenyl)-2-propenoic Acid Methyl Ester is used in the synthesis of AB3 and constitutional isomeric AB2 phenylpropyl ether-based supramolecular dendrimers. Also used in the synthesis of potent antagonists of leukotrines.

Technology Process of Methyl 4-hydroxycinnamate

There total 100 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%

methanol (67-56-1) + p-Coumaric Acid (7400-08-0,50940-26-6) → methyl 4-hydroxycinnamate (3943-97-3)

Guidance literature:

With sulfuric acid; for 24h; Reflux;

DOI:10.1016/j.ejmech.2014.11.055

Reference yield: 99.0%

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

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium acetate; In methanol; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/adsc.201000493

Reference yield: 98.0%

p-Coumaric Acid (7400-08-0,50940-26-6) → methyl 4-hydroxycinnamate (3943-97-3)

Guidance literature:

With sulfuric acid; In methanol; Heating / reflux;

upstream raw materials:

methanol

p-Coumaric Acid

4-hydroxyphenylacryloyl chloride

maleic acid

Downstream raw materials:

(E)-4-benzyloxycinnamic acid

(E)-methyl 3-(4-(benzyloxy)phenyl)acrylate

(E)-methyl-3-[4-(3-methylbut-2-enyloxy)phenyl]prop-2-enoate

1,15-Bis--pentadecan

Refernces

• 1、 Itoh, Atsuko,Kumashiro, Tomoko,Tanahashi, Takao,Nagakura, Naotaka,Nishi, Toyoyuki. "Flavonoid glycosides from Rhazya orientalis". . p. 352 - 357. Retrieved 2002.
• 2、 Beňová, Eva,Zeleňák, Vladimír,Halamová, Dá?a,Almá?i, Miroslav,Petrul'ová, Veronika,Psotka, Miroslav,Zeleňáková, Adriána,Ba?kor, Martin,Hornebecq, Virginie. "A drug delivery system based on switchable photo-controlled p-coumaric acid derivatives anchored on mesoporous silica". . p. 817 - 825. Retrieved 2017.
• 3、 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.
• 4、 -. "TRPV3 inhibitor and preparation method thereof". Paragraph 0240; 0241; 0242; 0243; 0244; 0245; 0246. . Retrieved 2021/04/10.