4-Acetoxycinnamic acid

Base Information

• Chemical Name: 4-Acetoxycinnamic acid
• CAS No.: 15486-19-8
• Molecular Formula: C₁₁H₁₀O₄
• Molecular Weight: 206.198
• Hs Code.: 2918990090
• European Community (EC) Number: 239-512-6
• NSC Number: 40967
• Nikkaji Number: J266.780K,J307.668G
• Wikidata: Q27159261
• Metabolomics Workbench ID: 70630
• Mol file: 15486-19-8.mol

Synonyms:4-Acetoxycinnamic acid;15486-19-8;p-Acetoxycinnamic acid;27542-85-4;3-(4-ACETOXYPHENYL)ACRYLIC ACID;trans-4-Acetoxycinnamic acid;4-Acetoxycinnamic acid, predominantly trans;(E)-3-(4-acetyloxyphenyl)prop-2-enoic acid;2-Propenoic acid, 3-[4-(acetyloxy)phenyl]-;(2E)-3-[4-(acetyloxy)phenyl]prop-2-enoic acid;2-Propenoic acid, 3-[4-(acetyloxy)phenyl]-, (2E)-;(E)-3-(4-Acetoxyphenyl)acrylic acid;(E)-3-(4-acetoxyphenyl)prop-2-enoic acid;3-[4-(acetyloxy)phenyl]prop-2-enoic acid;NSC-40967;SBB064754;2-Propenoic acid, 3-(4-(acetyloxy)phenyl)-;bmse010066;(E)-4-acetoxycinnamic acid;4-acetoxy-trans-cinnamic acid;SCHEMBL716835;SCHEMBL720473;CHEBI:86580;CBA54285;NSC40967;(E)-3-(4-Acetoxyphenyl)acrylicacid;MFCD00016847;3-[4-(acetyloxy)phenyl]acrylic acid;AKOS005068227;AKOS025311074;AC-16258;AS-14838;trans-3-(4-Acetoxyphenyl)-2-propenoic Acid;AQ-917/42754023;(2E)-3-[4-(Acetyloxy)phenyl]-2-propenoic acid #;W-108027;Q27159261

Chemical Property of 4-Acetoxycinnamic acid

Chemical Property:

• Vapor Pressure: 5.51E-06mmHg at 25°C
• Melting Point: 205-208°C
• Boiling Point: 209-211
• PKA: 4.39±0.10(Predicted)
• Flash Point: 144.4 °C
• PSA: 63.60000
• Density: 1.267g/cm³
• LogP: 1.70970
• Storage Temp.: 2-8°C
• 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: 262

Purity/Quality:

99% ^*data from raw suppliers

4-Acetoxycinnamicacid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-Acetoxycinnamic acid

There total 12 articles about 4-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: 97.0%

para-coumaric acid (7400-08-0,50940-26-6) + acetic anhydride (108-24-7) → 3-(4-acetoxyphenyl)acrylic acid (27542-85-4,50363-92-3,15486-19-8)

Guidance literature:

In pyridine; for 4h;

DOI:10.5012/bkcs.2013.34.12.3923

Reference yield: 78.0%

p-Coumaric Acid (7400-08-0,50940-26-6) + acetic anhydride (108-24-7) → 3-(4-acetoxyphenyl)acrylic acid (27542-85-4,50363-92-3,15486-19-8)

Guidance literature:

With pyridine;

Reference yield:

p-Coumaric Acid (7400-08-0,50940-26-6) → 3-(4-acetoxyphenyl)acrylic acid (27542-85-4,50363-92-3,15486-19-8)

Guidance literature:

With hydrogenchloride; dmap; acetic anhydride; In pyridine; water;

upstream raw materials:

sodium acetate

acetic anhydride

4-hydroxy-benzaldehyde

Ketene

Downstream raw materials:

p-Acetoxy-zimtsaeureazid

1-hydroxy-3-(4-acetoxyphenyl)-2-propen

N,N-biscoumaroyl 1,6-diaminohexane

C₂₆H₃₂N₂O₄

Refernces

• 1、 Sdykov et al.. "". . . Retrieved 1971.
• 2、 Hardegger, Leo A.,Humair, Roger,Sidler, Eric. "Toward a Scalable Synthesis and Process for EMA401, Part II: Development and Scale-Up of a Pyridine- A nd Piperidine-Free Knoevenagel-Doebner Condensation". . p. 1756 - 1762. Retrieved 2020/10/26.
• 3、 Gutiérrez Ortiz, Anggy Lusanna,Berti, Federico,Navarini, Luciano,Monteiro, Angelo,Resmini, Marina,Forzato, Cristina. "Synthesis of p-coumaroylquinic acids and analysis of their interconversion". . p. 419 - 427. Retrieved 2017/03/23.