Sinapyl alcohol

Base Information

• Chemical Name: Sinapyl alcohol
• CAS No.: 20675-96-1
• Molecular Formula: C11H14 O4
• Molecular Weight: 210.23
• European Community (EC) Number: 664-272-8
• UNII: 8O6NO04SMV
• ChEMBL ID: CHEMBL1800816
• DSSTox Substance ID: DTXSID501314695
• Metabolomics Workbench ID: 42198,124773
• Nikkaji Number: J246.056D,J304.419J
• Wikidata: Q418975
• Wikipedia: Sinapyl_alcohol
• Mol file: 20675-96-1.mol

Synonyms:sinapyl alcohol

Chemical Property of Sinapyl alcohol

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 210.08920892
• Heavy Atom Count: 15
• Complexity: 191

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Sinapyl alcohol

There total 37 articles about Sinapyl alcohol 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%

sinapyl acetate (94930-90-2) → trans-sinapyl alcohol (20675-96-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -10 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)87715-1 DOI:10.1021/jo00207a006

Reference yield: 100.0%

4-hydroxy-3,5-dimethoxycinnamic acid methyl ester (42041-51-0,67460-46-2,20733-94-2) → Syringenin (20675-96-1,104330-63-4,537-33-7)

Guidance literature:

With 1-bromo-butane; lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - 20 ℃; Cooling with acetone-dry ice; Inert atmosphere;

DOI:10.1039/c5gc01334h

Reference yield: 97.0%

methyl (E)-sinapate (42041-51-0) → trans-sinapyl alcohol (20675-96-1)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 - 20 ℃; for 1h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201701021

upstream raw materials:

syringin

(E)-sinapinaldehyde

3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde

5-hydroxyconiferyl alcohol

Downstream raw materials:

(+/-)-syringaresinol

4-(2,4-dinitrophenoxy)-3,5-dimethoxycinnamyl alcohol

syringin

3'-O-methylxanthocercin A

Refernces

• 1、 Simon, Clémence,Lion, Cédric,Ahouari, Hania,Vezin, Hervé,Hawkins, Simon,Biot, Christophe. "EPR imaging of sinapyl alcohol and its application to the study of plant cell wall lignification". . p. 387 - 390. Retrieved 2021.
• 2、 Kim, Hoon,Ralph, John. "Simplified preparation of coniferyl and sinapyl alcohols". . p. 3693 - 3695. Retrieved 2005.
• 3、 Dong, Hongbo,Du, Weihong,He, Yujiao,Shi, Zheng,Wang, Yingying,Wu, Min. "Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues". . p. 2866 - 2874. Retrieved 2021/11/12.