3,4,5-Trimethoxycinnamic acid

Base Information

• Chemical Name: 3,4,5-Trimethoxycinnamic acid
• CAS No.: 20329-98-0
• Molecular Formula: C₁₂H₁₄O₅
• Molecular Weight: 238.24
• European Community (EC) Number: 201-999-8
• NSC Number: 66175
• UNII: C9096D920O
• DSSTox Substance ID: DTXSID701298647
• Nikkaji Number: J11F,J209.021J
• Wikidata: Q30061098
• Metabolomics Workbench ID: 38170
• ChEMBL ID: CHEMBL501235
• Mol file: 20329-98-0.mol

Synonyms:3,4,5-trimethoxycinnamic acid;3-(3,4,5-trimethoxyphenyl)-2-propenoic acid

Chemical Property of 3,4,5-Trimethoxycinnamic acid

Chemical Property:

• Vapor Pressure: 5.39E-07mmHg at 25°C
• Melting Point: 125-127 °C(lit.)
• Boiling Point: 396.4°C at 760 mmHg
• PKA: 4.48±0.10(Predicted)
• Flash Point: 151.5°C
• PSA: 64.99000
• Density: 1.209±0.06 g/cm3(Predicted)
• LogP: 1.81020
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 238.08412354
• Heavy Atom Count: 17
• Complexity: 262

Purity/Quality:

98%,99%, ^*data from raw suppliers

(E)-3,4,5-Trimethoxycinnamic Acid >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C=CC(=O)O
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)O

Technology Process of 3,4,5-Trimethoxycinnamic acid

There total 21 articles about 3,4,5-Trimethoxycinnamic 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%

malonic acid (141-82-2) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) → (E)-3,4,5-trimethoxy-cinnamic acid (20329-98-0,20329-99-1,90-50-6)

Guidance literature:

With piperidine; pyridine; for 1h; Reflux;

DOI:10.2174/1573406415666190627103013

Reference yield: 89.0%

malonic acid (141-82-2) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) → 3,4,5-trimethoxy styrene (13400-02-7) + (E)-3,4,5-trimethoxy-cinnamic acid (20329-98-0,20329-99-1,90-50-6)

Guidance literature:

With pyridine; acetic acid; at 130 ℃; for 0.133333h; microwave irradiation;

DOI:10.1016/j.tet.2006.11.023

Reference yield: 83.0%

3,4,5-trimethoxycinnamaldehyde (71277-13-9,34346-90-2,71277-12-8) → (E)-3,4,5-trimethoxy-cinnamic acid (20329-98-0,20329-99-1,90-50-6)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; In water; dimethyl sulfoxide; at 0 - 20 ℃; for 23h; Inert atmosphere;

DOI:10.1021/acs.joc.5b01776

upstream raw materials:

ethyl trimethoxybenzoyl acetate

malonic acid

3,4,5-trimethoxy-benzaldehyde

diazomethane

Downstream raw materials:

3,4,5-trimethoxy-trans-cinnamic acid-(3-pyrrolidino-propyl ester)

3,4,5-trimethoxy-trans-cinnamic acid-(3-piperidino-propyl ester)

3,4,5-trimethoxy-trans-cinnamic acid-(3-morpholino-propyl ester)

3-(3,4,5-trimethoxyphenyl)propanoic acid

Refernces

• 1、 Das, Aniruddha,Anbu, Nagaraj,Gogoi, Chiranjib,Dhakshinamoorthy, Amarajothi,Biswas, Shyam. "Amino Group Functionalized Hf-Based Metal-Organic Framework for Knoevenagel-Doebner Condensation". . p. 3396 - 3403. Retrieved 2021/08/20.
• 2、 Do Nascimento, Mayara S. S.,Camara, Vitória R. F.,da Costa, Juliana S.,Barbosa, Juliana M. C.,Lins, Alessandra S. M.,Salom?o, Kelly,de Castro, Solange L.,Carvalho, Samir A.,da Silva, Edson F.,Fraga, Carlos A. M.. "Identification of novel functionalized carbohydrazonamides designed as chagas disease drug candidates". . p. 774 - 783. Retrieved 2020/08/19.