2-Acetoxycinnamic acid

Base Information

• Chemical Name: 2-Acetoxycinnamic acid
• CAS No.: 16189-10-9
• Molecular Formula: C11H10 O4
• Molecular Weight: 206.198
• European Community (EC) Number: 925-867-0,676-593-0
• NSC Number: 98725
• DSSTox Substance ID: DTXSID70876299
• Nikkaji Number: J78.721C,J3.187.463G
• Mol file: 16189-10-9.mol

Synonyms:2-Acetoxycinnamic acid;55620-18-3;Tylmarin;16189-10-9;o-Acetoxycinnamic acid;O-Acetyl-o-coumaric acid;2-Acetylcoumaric acid;3-(2-Acetoxyphenyl)acrylic acid;CINNAMIC ACID, 2-ACETOXY-;(E)-3-(2-acetyloxyphenyl)prop-2-enoic acid;Cinnamic acid, o-hydroxy-, acetate;NSC 98725;3-(2-(Acetyloxy)phenyl)-2-propenoic acid;2-Propenoic acid, 3-(2-(acetyloxy)phenyl)-;2-Acetoxycinnamic acid, predominantly trans;2-Propenoic acid, 3-[2-(acetyloxy)phenyl]-;2-Propenoic acid,3-[2-(acetyloxy)phenyl]-, (2E)-;3-[2-(Acetyloxy)phenyl]-2-propenoic acid;2-Acetpxycinnamic acid;2-ACETOXYCINNAMICACID;(E)-3-(2-acetoxyphenyl)acrylic acid;SCHEMBL1711263;DTXSID70876299;UXOWQQCLBQBRMQ-VOTSOKGWSA-N;NSC98725;MFCD00014375;NSC-98725;STL220645;AKOS016026220;(2E)-3-(2-Acetoxyphenyl)acrylic acid;AS-35522;LS-54028;(E)-3-(2-acetoxyphenyl)prop-2-enoic acid;2-Propenoic acid,3-[2-(acetyloxy)phenyl]-;CS-0128408;(E)-3-(2-acetyloxyphenyl)-2-propenoic acid;(2E)-3-[2-(acetyloxy)phenyl]prop-2-enoic acid;A830724;A883046;2-Propenoic acid, 3-[2-(acetyloxy)phenyl]-, (E)-

Chemical Property of 2-Acetoxycinnamic acid

Chemical Property:

• Vapor Pressure: 4.75E-06mmHg at 25°C
• Refractive Index: 1.592
• Boiling Point: 367.5°Cat760mmHg
• Flash Point: 145.4°C
• Density: 1.267g/cm³
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 206.05790880
• Heavy Atom Count: 15
• Complexity: 270

Purity/Quality:

99%min ^*data from raw suppliers

2-Acetylcoumaricacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=CC=CC=C1C=CC(=O)O
• Isomeric SMILES: CC(=O)OC1=CC=CC=C1/C=C/C(=O)O

Technology Process of 2-Acetoxycinnamic acid

There total 5 articles about 2-Acetoxycinnamic 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: 100.0%

o-Coumaric acid (614-60-8) + acetic anhydride (108-24-7) → (E)-3-<2-(acetyloxy)phenyl>-2-propenoic acid (16189-10-9)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(99)00121-0

Reference yield: 27.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 2-acetoxybenzaldehyde (5663-67-2) → (E)-3-<2-(acetyloxy)phenyl>-2-propenoic acid (16189-10-9) + (E)-3-(2-Acetoxy-phenyl)-2-(ethoxy-hydroxy-phosphoryl)-acrylic acid

Guidance literature:

With potassium carbonate; In methanol;

Reference yield:

acetic anhydride (108-24-7) + salicylaldehyde (90-02-8) → (E)-3-<2-(acetyloxy)phenyl>-2-propenoic acid (16189-10-9) + coumarin (91-64-5)

Guidance literature:

With sodium acetate;

upstream raw materials:

o-Coumaric acid

acetic anhydride

salicylaldehyde

diethoxyphosphoryl-acetic acid ethyl ester

Downstream raw materials:

coumarin

acetic acid

o-Coumaric acid

2-<(Z)-3-(benzylamino)-3-oxo-1-propenyl>phenyl acetate

Refernces

• 1、 Nong, Wenqian,Zhao, Anran,Wei, Jinrui,Cheng, Hui,Luo, Xuan,Lin, Cuiwu. "Synthesis of a series of benzothiazole amide derivatives and their biological evaluation as potent hemostatic agents". . p. 6231 - 6241. Retrieved 2018/02/19.
• 2、 Nong, Wenqian,Zhao, Anran,Wei, Jinrui,Lin, Xiao,Wang, Lisheng,Lin, Cuiwu. "Synthesis and biological evaluation of a new series of cinnamic acid amide derivatives as potent haemostatic agents containing a 2-aminothiazole substructure". supporting information. p. 4506 - 4511. Retrieved 2017/09/12.