Cinnamic acid, (3,4,5-trimethoxy)thio-, O-ethyl ester

Base Information

• Chemical Name: Cinnamic acid, (3,4,5-trimethoxy)thio-, O-ethyl ester
• CAS No.: 117666-86-1
• Molecular Formula: C₁₄H₁₈O₄S
• Molecular Weight: 282.361
• Nikkaji Number: J3.394.919G
• Wikidata: Q76390028
• ChEMBL ID: CHEMBL1911038
• Mol file: 117666-86-1.mol

Synonyms:ethyl 3',4',5'-trimethoxythionocinnamate;ETMTC cpd

Chemical Property of Cinnamic acid, (3,4,5-trimethoxy)thio-, O-ethyl ester

Chemical Property:

• Vapor Pressure: 6.22E-06mmHg at 25°C
• Boiling Point: 389.8°C at 760 mmHg
• Flash Point: 189.6°C
• PSA: 69.01000
• Density: 1.144g/cm³
• LogP: 3.08950
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 282.09258022
• Heavy Atom Count: 19
• Complexity: 292

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=S)C=CC1=CC(=C(C(=C1)OC)OC)OC
• Isomeric SMILES: CCOC(=S)/C=C/C1=CC(=C(C(=C1)OC)OC)OC

Technology Process of Cinnamic acid, (3,4,5-trimethoxy)thio-, O-ethyl ester

There total 3 articles about Cinnamic acid, (3,4,5-trimethoxy)thio-, O-ethyl ester 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: 63.0%

3,4,5-trimethoxycinnamic acid ethyl ester (1878-29-1) → ethyl 3',4',5'-trimethoxythionocinnamate (117666-86-1)

Guidance literature:

With tetraphosphorus decasulfide; In 1,4-dioxane; Reflux;

DOI:10.1016/j.ejmech.2011.09.008

Reference yield:

O-Ethyl thioacetate (926-67-0) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) → ethyl 3',4',5'-trimethoxythionocinnamate (117666-86-1)

Guidance literature:

With sodium ethanolate; In ethanol; at 5 ℃;

Reference yield:

3,4,5-trimethoxycinnamic acid (90-50-6) → ethyl 3',4',5'-trimethoxythionocinnamate (117666-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 70 °C

2: tetraphosphorus decasulfide / 1,4-dioxane / Reflux

With tetraphosphorus decasulfide; sulfuric acid; In 1,4-dioxane;

DOI:10.1016/j.ejmech.2011.09.008

upstream raw materials:

O-Ethyl thioacetate

3,4,5-trimethoxy-benzaldehyde

3,4,5-trimethoxycinnamic acid

3,4,5-trimethoxycinnamic acid ethyl ester

Refernces

Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells

10.1016/j.ejmech.2011.09.008

The research investigates the design, synthesis, and evaluation of novel cinnamate, thiocinnamate, and thionocinnamate analogs derived from natural products for their ability to inhibit the expression of cell adhesion molecules (CAMs) on human endothelial cells. The study aims to identify potent inhibitors of TNF-α-induced ICAM-1, VCAM-1, and E-selectin expression, which are critical in inflammatory responses. The key chemicals used include various cinnamates, thiocinnamates, and thionocinnamates, with ethyl 3,4,5-trimethoxythionocinnamate (ETMTC) emerging as the most potent inhibitor. The research concludes that these compounds, particularly ETMTC, significantly inhibit the expression of CAMs and neutrophil adhesion to endothelial cells, suggesting their potential as anti-inflammatory agents. The findings highlight the importance of the alkyl chain length, the number of methoxy groups, and the presence of sulfur in the structure for enhancing inhibitory activity.

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