Methyl sinapate

Base Information

• Chemical Name: Methyl sinapate
• CAS No.: 20733-94-2
• Molecular Formula: C₁₂H₁₄O₅
• Molecular Weight: 238.24
• Hs Code.: 2918990090
• Nikkaji Number: J248.130H,J662.255K
• Metabolomics Workbench ID: 70618
• ChEMBL ID: CHEMBL146713
• Mol file: 20733-94-2.mol

Synonyms:antithiamine factor;methyl sinapate

Chemical Property of Methyl sinapate

Chemical Property:

• Vapor Pressure: 4.55E-06mmHg at 25°C
• Melting Point: 89.9-90.7 °C(Solv: carbon tetrachloride (56-23-5))
• Boiling Point: 372.3°Cat760mmHg
• PKA: 8.90±0.23(Predicted)
• Flash Point: 140.6°C
• PSA: 64.99000
• Density: 1.21g/cm³
• LogP: 1.59560
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.8
• 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% ^*data from raw suppliers

Methyl3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C=CC(=O)OC
• Isomeric SMILES: COC1=CC(=CC(=C1O)OC)/C=C/C(=O)OC

Technology Process of Methyl sinapate

There total 5 articles about Methyl sinapate 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: 98.0%

methanol (67-56-1) + sinapinic acid (530-59-6,7362-37-0) → 4-hydroxy-3,5-dimethoxycinnamic acid methyl ester (42041-51-0,67460-46-2,20733-94-2)

Guidance literature:

With sulfuric acid; Reflux;

DOI:10.1080/14786419.2017.1317776

Reference yield: 95.0%

sinapinic acid (530-59-6,7362-37-0) + acetyl chloride (75-36-5) → 4-hydroxy-3,5-dimethoxycinnamic acid methyl ester (42041-51-0,67460-46-2,20733-94-2)

Guidance literature:

In methanol; for 1h; Inert atmosphere; Reflux;

DOI:10.1039/c5gc01334h

Reference yield:

(3S,5R,6S,7E,9R)-7-megastigmene-3,6,9-triol 3-O-β-D-(6'-O-sinapoyl)glucopyranoside + sodium methylate (124-41-4) → 4-hydroxy-3,5-dimethoxycinnamic acid methyl ester (42041-51-0,67460-46-2,20733-94-2) + dendranthemoside A

Guidance literature:

In methanol; at 20 ℃; for 4h;

DOI:10.1016/j.phytochem.2010.10.003

upstream raw materials:

methanol

sinapinic acid

sodium methylate

acetyl chloride

Downstream raw materials:

8-(4-hydroxy-3,5-dimethoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromen-6-one

sinapinic acid

methyl (E)-3-[2-(4-hydroxy-3,5-dimethoxyphenyl)-7-hydroxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]propen-2-enoate

C₂₄H₂₈O₁₀

Refernces

• 1、 Xu, Manyi,Li, Na,Zhao, Zihao,Shi, Zhixian,Sun, Jianbo,Chen, Li. "Design, synthesis and antitumor evaluation of novel celastrol derivatives". . p. 265 - 276. Retrieved 2019/05/04.
• 2、 Lancefield,Westwood. "The synthesis and analysis of advanced lignin model polymers". supporting information. p. 4980 - 4990. Retrieved 2015/11/16.