4-Acetoxy-3-methoxycinnamic acid

Base Information

• Chemical Name: 4-Acetoxy-3-methoxycinnamic acid
• CAS No.: 34749-55-8
• Molecular Formula: C₁₂H₁₂O₅
• Molecular Weight: 236.224
• European Community (EC) Number: 636-753-2
• NSC Number: 16957
• DSSTox Substance ID: DTXSID6062545,DTXSID301205242
• Nikkaji Number: J1.190.993K,J308.133H
• Wikidata: Q27159264
• Metabolomics Workbench ID: 70624
• ChEMBL ID: CHEMBL33539
• Mol file: 34749-55-8.mol

Synonyms:4-Acetoxy-3-methoxycinnamic acid;2596-47-6;Acetylferulic acid;3-(4-acetoxy-3-methoxyphenyl)acrylic acid;3-Methoxy-4-acetoxycinnamic acid;Cinnamic acid, 4-acetoxy-3-methoxy-;2-Propenoic acid, 3-[4-(acetyloxy)-3-methoxyphenyl]-;34749-55-8;O-acetylferulic acid;(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid;(E)-3-(4-acetyloxy-3-methoxyphenyl)prop-2-enoic acid;CHEBI:86582;Cinnamic acid, 4-hydroxy-3-methoxy-, acetate;MFCD00014378;NSC 16957;2-Propenoic acid, 3-(4-(acetyloxy)-3-methoxyphenyl)-;trans-4-Acetoxy-3-methoxycinnamic acid;(2E)-3-[4-(acetyloxy)-3-methoxyphenyl]prop-2-enoic acid;AI3-23455;(E)-3-(4-acetoxy-3-methoxy-phenyl)prop-2-enoic acid;trans-3-[4-acetyloxy-3-methoxyphenyl]-2-propenoic acid;SBB016646;bmse010048;trans-4-o-acetylferulic acid;CHEMBL33539;SCHEMBL111271;DTXSID6062545;(2E)-3-[4-(ACETYLOXY)-3-METHOXYPHENYL]ACRYLIC ACID;DTXSID301205242;AMY41525;NSC16957;NSC-16957;AKOS000304792;AS-10137;CS-0128888;(E)3-(4-acetoxy-3-methoxyphenyl)acrylic acid;3-(4-acetoxy-3-methoxyphenyl)-2-propenoic acid;A818110;(e)-3-(4-acetoxy-3-methoxyphenyl)prop-2-enoic acid;Q27159264;(2E)-3-[4-(Acetyloxy)-3-methoxyphenyl]-2-propenoic acid;trans-3-[4-acetyloxy-3-methoxy-phenyl]-2-propenoic acid;(2E)-3-[4-(Acetyloxy)-3-methoxyphenyl]-2-propenoic acid #

Chemical Property of 4-Acetoxy-3-methoxycinnamic acid

Chemical Property:

• PSA: 0.00000
• LogP: 0.00000
• Solubility.: Dichloromethane; Methanol
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 236.06847348
• Heavy Atom Count: 17
• Complexity: 310

Purity/Quality:

HPLC ≥ 98% ^*data from raw suppliers

trans-4-Acetoxy-3-methoxycinnamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1=C(C=C(C=C1)C=CC(=O)O)OC
• Isomeric SMILES: CC(=O)OC1=C(C=C(C=C1)/C=C/C(=O)O)OC
• Uses: trans-4-Acetoxy-3-methoxycinnamic Acid is an intermediate in synthesizing 3-O-(E)-Feruloylquinic Acid (F308980), a phenolic acid with potential antioxidant and antifungal activities. Secondary metabolite in the coffee brewing process.

Technology Process of 4-Acetoxy-3-methoxycinnamic acid

There total 26 articles about 4-Acetoxy-3-methoxycinnamic 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%

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + acetic anhydride (108-24-7) → (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid (2596-47-6,147677-05-2,34749-55-8)

Guidance literature:

With pyridine; at 37 ℃; Inert atmosphere;

DOI:10.1021/jf506361r

Reference yield: 99.0%

3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + acetic anhydride (108-24-7) → 3-(4-acetoxy-3-methoxyphenyl)prop-2-enoic acid (34749-55-8,147677-05-2,2596-47-6)

Guidance literature:

With pyridine; dmap; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetasy.2013.06.002

Reference yield: 92.0%

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) → (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid (2596-47-6,147677-05-2,34749-55-8)

Guidance literature:

With hydrogenchloride; acetic anhydride; In pyridine; ethyl acetate;

upstream raw materials:

vanillin acetate

acetic anhydride

sodium acetate

vanillin

Downstream raw materials:

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

acetic acid

acetic acid 4-{2-[2-(1H-indol-3-yl)-ethylcarbamoyl]-vinyl}-2-methoxy-phenyl ester

(E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

Refernces

• 1、 Yasmin, Sabina,Cerchia, Carmen,Badavath, Vishnu Nayak,Laghezza, Antonio,Dal Piaz, Fabrizio,Mondal, Susanta K.,Atl?, ?zlem,Baysal, Merve,Vadivelan, Sankaran,Shankar,Siddique, Mohd Usman Mohd,Pattnaik, Ashok Kumar,Singh, Ravi Pratap,Loiodice, Fulvio,Jayaprakash, Venkatesan,Lavecchia, Antonio. "A Series of Ferulic Acid Amides Reveals Unexpected Peroxiredoxin 1 Inhibitory Activity with in vivo Antidiabetic and Hypolipidemic Effects". . p. 484 - 498. Retrieved 2020/11/02.
• 2、 Moni, Lisa,Banfi, Luca,Basso, Andrea,Mori, Alessia,Risso, Federica,Riva, Renata,Lambruschini, Chiara. "A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives". . p. 1737 - 1749. Retrieved 2021/03/23.