2',3,4,4',6'-Pentahydroxychalcone

Base Information

• Chemical Name: 2',3,4,4',6'-Pentahydroxychalcone
• CAS No.: 73692-51-0
• Molecular Formula: C15H12 O6
• Molecular Weight: 288.257
• European Community (EC) Number: 277-569-9
• UNII: MDQ6NJ9LSN
• DSSTox Substance ID: DTXSID201343534
• Nikkaji Number: J295.250E
• Wikidata: Q27108675,Q76306514
• Metabolomics Workbench ID: 26747
• ChEMBL ID: CHEMBL127409
• Mol file: 73692-51-0.mol

Synonyms:Eriodictyol chalcone;14917-41-0;(E)-3-(3,4-dihydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one;2',3,4,4',6'-Pentahydroxychalcone;2',4',6',3,4-Pentahydroxychalcone;3,4,2',4',6'-Pentahydroxychalcone;73692-51-0;Eriodictyolchalcone;MDQ6NJ9LSN;CHEMBL127409;CHEBI:48967;EINECS 277-569-9;3,4,2',4',6-Pentahydroxychalcone;2',3,4,4',6'-Penta-hydroxychalcone;(2E)-3-(3,4-dihydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one;2-Propen-1-one, 3-(3,4-dihydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-, (2E)-;PENTAHYDROXYCHALCONE,2,4,6,3,4-(SH);(2E)-3-(3,4-Dihydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one;2-Propen-1-one, 3-(3,4-dihydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-;UNII-MDQ6NJ9LSN;SCHEMBL159248;CHEBI:10836;GTPL12443;CRBYNQCDRNZCNX-DUXPYHPUSA-N;DTXSID201343534;HY-N9551;BDBM50042994;LMPK12120271;MFCD00017302;AKOS024465134;3,4,2/',4/',6/'-Pentahydroxychalcone;trans-2',3,4,4',6'-pentahydroxychalcone;CS-0201229;trans-2'',3,4,4'',6''-pentahydroxychalcone;Q27108675;3-(3,4-dihydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one

Chemical Property of 2',3,4,4',6'-Pentahydroxychalcone

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 288.06338810
• Heavy Atom Count: 21
• Complexity: 384

Purity/Quality:

99% ^*data from raw suppliers

2',4',6',3,4-Pentahydroxychalcone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=CC(=O)C2=C(C=C(C=C2O)O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1/C=C/C(=O)C2=C(C=C(C=C2O)O)O)O)O

Technology Process of 2',3,4,4',6'-Pentahydroxychalcone

There total 7 articles about 2',3,4,4',6'-Pentahydroxychalcone 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: 68.0%

C19H20O8 → 2',3,4,4',6'-pentahydroxychalcone (73692-51-0)

Guidance literature:

With hydrogenchloride; In methanol; water; for 0.5h; Reflux;

DOI:10.1007/s00044-011-9640-2

Reference yield:

3,5-dihydroxyphenol (108-73-6) + caffeic acid chloride (23416-69-5) → 2',3,4,4',6'-pentahydroxychalcone (73692-51-0)

Guidance literature:

caffeic acid chloride; With aluminum (III) chloride; In dichloromethane; at 5 - 10 ℃; for 2h; Large scale;

3,5-dihydroxyphenol; In dichloromethane; at 10 - 20 ℃; for 4h; Large scale;

Reference yield:

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) → 2',3,4,4',6'-pentahydroxychalcone (73692-51-0)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetone

2: potassium hydroxide / ethanol

3: hydrogenchloride / methanol; water / 0.5 h / Reflux

With hydrogenchloride; potassium carbonate; potassium hydroxide; In methanol; ethanol; water; acetone; 2: Claisen Schmidt condensation;

DOI:10.1007/s00044-011-9640-2

upstream raw materials:

2,4,6-trihydroxyacetophenone

2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone

3,5-dihydroxyphenol

caffeic acid chloride

Downstream raw materials:

eriodictyol

aureusidin

Refernces

• 1、 -. "A natural active product process for synthesis of dihydro-quercetin (by machine translation)". Paragraph 0019; 0020. . Retrieved 2017/02/24.