Coumarinic acid

Base Information

• Chemical Name: Coumarinic acid
• CAS No.: 495-79-4
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• UNII: 388YT9184W
• Metabolomics Workbench ID: 49435
• Nikkaji Number: J2.367.125E
• Wikidata: Q27103936
• Mol file: 495-79-4.mol

Synonyms:Coumarinic acid;cis-o-Coumaric acid;cis-o-Hydroxycinnamic acid;2-Coumarinate;o-Hydroxycinnamic acid, cis-;(Z)-form;2-Hydroxycinnamic acid, (2Z)-;Cinnamic acid, o-hydroxy-, (Z)-;388YT9184W;495-79-4;UNII-388YT9184W;2-Propenoic acid, 3-(2-hydroxyphenyl)-, (Z)-;2-Propenoic acid, 3-(2-hydroxyphenyl)-, (2Z)-;(2Z)-3-(2-hydroxyphenyl)prop-2-enoic acid;cis-2-Hydroxycinnamate;Cumarinsaure;cis-2-coumaric acid;cis-2-Hydroxy cinnamate;(Z)-3-(2-hydroxyphenyl)prop-2-enoic acid;cis-2-hydroxycinnamic acid;(2Z)-2-hydroxycinnamic acid;SCHEMBL892006;CHEBI:28873;PMOWTIHVNWZYFI-WAYWQWQTSA-N;Cinnamic acid, 2-hydroxy-, cis-;HY-N12038;(2Z)-3-(2-hydroxyphenyl)acrylic acid;Cinnamic acid, O-hydroxy-, (Z)- (8CI);3-(2-Hydroxyphenyl)-(Z)-2-Propenoic acid;CS-0890953;3-(2-Hydroxyphenyl)-(2Z)-2-Propenoic acid;3-(2-Hydroxyphenyl)-2-propenoic acid, 9CI;C05838;Q27103936;7AF78CE0-7D8B-427A-8189-578C732F4E8E

Chemical Property of Coumarinic acid

Chemical Property:

• PSA: 57.53000
• LogP: 1.49000
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 186

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C=CC(=O)O)O
• Isomeric SMILES: C1=CC=C(C(=C1)/C=C\C(=O)O)O

Technology Process of Coumarinic acid

There total 15 articles about Coumarinic 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%

2-Iodophenol (533-58-4) + acrylic acid (79-10-7) → 2-hydroxycinnamic acid (495-79-4,583-17-5,614-60-8)

Guidance literature:

With potassium hydroxide; In water; at 90 ℃; for 5h;

DOI:10.3390/molecules16119067

Reference yield: 85.0%

2-hydroxybromobenzene (95-56-7) + acrylic acid (79-10-7) → 2-hydroxycinnamic acid (495-79-4,583-17-5,614-60-8)

Guidance literature:

With potassium carbonate; In water; at 90 ℃; for 5h; Green chemistry;

DOI:10.1002/aoc.3707

Reference yield: 79.0%

malonic acid (141-82-2) + salicylaldehyde (90-02-8) → 2-hydroxycinnamic acid (495-79-4,583-17-5,614-60-8)

Guidance literature:

With hydroxyapatite supported caesium carbonate; In water; at 80 ℃; for 3.5h;

DOI:10.3762/bjoc.5.68

upstream raw materials:

malonic acid

4-hydroxy-benzaldehyde

meta-hydroxybenzaldehyde

salicylaldehyde

Downstream raw materials:

methyl 2-coumarate

N,N-dimethyl-aniline

(E)-3-(2-Benzyloxy-phenyl)-acrylic acid methyl ester

salicylaldehyde

Refernces

• 1、 Tabatabaei Rezaei, Seyed Jamal,Shamseddin, Azin,Ramazani, Ali,Mashhadi Malekzadeh, Asemeh,Azimzadeh Asiabi, Pegah. "Palladium nanoparticles immobilized on amphiphilic and hyperbranched polymer-functionalized magnetic nanoparticles: An efficient semi-heterogeneous catalyst for Heck reaction". . . Retrieved 2017/09/01.
• 2、 Ohtaka, Atsushi,Yamaguchi, Tomohiro,Teratani, Takuto,Shimomura, Osamu,Nomura, Ryoki. "Linear polystyrene-stabilized PdO nanoparticle-catalyzed mizoroki-heck reactions in water". experimental part. p. 9067 - 9076. Retrieved 2012/01/03.