Afzelechin

Base Information

• Chemical Name: Afzelechin
• CAS No.: 2545-00-8
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.273
• UNII: W782YDV47U
• DSSTox Substance ID: DTXSID60300139
• Nikkaji Number: J14.392H
• Wikipedia: Afzelechin
• Wikidata: Q23068576
• Metabolomics Workbench ID: 21865
• ChEMBL ID: CHEMBL3437595
• Mol file: 2545-00-8.mol

Synonyms:(2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol;afzelechin

Chemical Property of Afzelechin

Chemical Property:

• Vapor Pressure: 1.89E-14mmHg at 25°C
• Melting Point: 252-254 °C (decomp)
• Boiling Point: 583.4°Cat760mmHg
• PKA: 9?+-.0.60(Predicted)
• Flash Point: 306.6°C
• PSA: 90.15000
• Density: 1.492g/cm³
• LogP: 1.84050
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 274.08412354
• Heavy Atom Count: 20
• Complexity: 328

Purity/Quality:

99% ^*data from raw suppliers

AFZELECHIN 98.5 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O
• Isomeric SMILES: C1[C@@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O

Technology Process of Afzelechin

There total 52 articles about Afzelechin 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: 82.0%

(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-ol (773859-58-8) → (-)-epiafzelechin (490-61-9,2545-00-8,19879-28-8,24808-04-6,36801-69-1)

Guidance literature:

With hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 6h;

DOI:10.1016/j.tet.2004.06.113

Reference yield: 81.0%

(+)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-ol (773859-54-4) → (+)-afzelechin (490-61-9,19879-28-8,24808-04-6,36801-69-1,2545-00-8)

Guidance literature:

With hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 6h;

DOI:10.1016/j.tet.2004.06.113

Reference yield:

PZ-5 → (-)-epiafzelechin (490-61-9,2545-00-8,19879-28-8,24808-04-6,36801-69-1) + catechin (154-23-4) + epigallocatechin (970-73-0,1617-55-6,3371-27-5,13425-13-3,136892-45-0,970-74-1,98032-84-9)

Guidance literature:

PZ-5; With thiophenol;

With nickel; acetic acid; In ethanol; at 50 ℃; for 1h;

DOI:10.1023/A:1015773513717

upstream raw materials:

epiafzelechin-(4β-8)-benzylthioether

(-)-epi-afzlechin(4β->8)(-)-epi-afzelechin

(-)-epiafzelechin 7-O-β-D-glucopyranoside

epi-Afzelechin gallate

Downstream raw materials:

catechin

(2S)-7,4'-dihydroxyflavan-(4β->6)-epiafzelechin

(2S)-7,4'-dihydroxyflavan-(4α->6)-epiafzelechin

(2S)-7,4'-dihydroxyflavan-(4β->8)-epiafzelechin

Refernces

• 1、 Wan, Sheng Biao,Chan, Tak Hang. "Enantioselective synthesis of afzelechin and epiafzelechin". . p. 8207 - 8211. Retrieved 2007/10/03.
• 2、 Nel, Reinier J. J.,Heerden, Pieter S. van,Rensburg, Hendrik van,Ferreira, Daneel. "Stereoselective Synthesis of Flavonoids. Part 8. Free Phenolic Flavan-3-ol Diastereomers". . p. 2610 - 2625. Retrieved 2007/10/03.