2-Hydroxycinnamic acid

Base Information

• Chemical Name: 2-Hydroxycinnamic acid
• CAS No.: 614-60-8
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• European Community (EC) Number: 210-386-4
• NSC Number: 32952
• UNII: 23AU5FZB9C
• DSSTox Substance ID: DTXSID10883240
• Nikkaji Number: J55.415D,J7.442J
• Wikipedia: o-coumaric acid
• Wikidata: Q7072006
• Metabolomics Workbench ID: 38182
• ChEMBL ID: CHEMBL52564
• Mol file: 614-60-8.mol

Synonyms:2-hydroxycinnamic acid;2-hydroxycinnamic acid, (E)-isomer;2-hydroxycinnamic acid, (Z)-isomer;ortho-hydroxycinnamic acid

Chemical Property of 2-Hydroxycinnamic acid

Chemical Property:

• Appearance/Colour: off-white to beige powder
• Vapor Pressure: 1.94E-05mmHg at 25°C
• Melting Point: 217 °C (dec.)(lit.)
• Refractive Index: 1.66
• Boiling Point: 348 °C at 760 mmHg
• PKA: pK1:4.614 (25°C)
• Flash Point: 178.5 °C
• PSA: 57.53000
• Density: 1.329 g/cm³
• LogP: 1.49000
• Storage Temp.: Store below +30°C.
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly)
• 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:

HPLC≥98% ^*data from raw suppliers

trans-2-Hydroxycinnamic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-24/25-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• 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 2-Hydroxycinnamic acid

There total 52 articles about 2-Hydroxycinnamic 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: 90.0%

2-Iodophenol (533-58-4) + acrylic acid (79-10-7) → o-Coumaric acid (614-60-8)

Guidance literature:

With palladium diacetate; potassium acetate; potassium carbonate; In water; at 50 ℃; for 1.5h;

Reference yield: 78.1%

3-methyl-4-nitro-5-<2-(2-hydroxyphenyl)ethenyl>isoxazole (85364-66-5) → o-Coumaric acid (614-60-8)

Guidance literature:

With sodium hydroxide; for 2h; Heating;

Reference yield: 75.0%

(coumarin-3-yl)triphenylphosphonium perchlorate → o-Coumaric acid (614-60-8)

Guidance literature:

With sodium hydroxide; In water; for 0.0833333h; Heating;

DOI:10.1023/A:1023374120316

upstream raw materials:

2-amino-cinnamic acid

3-(2-hydroxy-phenyl)-3-sulfo-propionic acid

coumarin

acetic anhydride

Downstream raw materials:

2-allylphenol

methylammonium carbonate

(E)-4-(2-hydroxyphenyl)but-3-en-2-one

(E)-3-(2-ethoxyphenyl)prop-2-enoic acid

Refernces

• 1、 Patzak,Neugebauer. "-". . p. 662,670. Retrieved 1951.
• 2、 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.
• 3、 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.