Naringenin chalcone

Base Information

• Chemical Name: Naringenin chalcone
• CAS No.: 25515-46-2
• Molecular Formula: C15H12 O5
• Molecular Weight: 272.257
• European Community (EC) Number: 860-137-4
• UNII: YCF6Z24AS2
• ChEMBL ID: CHEMBL338066
• DSSTox Substance ID: DTXSID101043553
• Metabolomics Workbench ID: 26740
• Nikkaji Number: J16.987K,J258.627D
• Pharos Ligand ID: MNZP3NJ7L6WR
• Wikidata: Q25098661,Q27467486
• Wikipedia: Naringenin_chalcone
• Mol file: 25515-46-2.mol

Synonyms:2',4,4',6'-tetrahydroxychalcone;chalconaringenin;naringenin chalcone;naringenin chalcone, (E)-isomer

Chemical Property of Naringenin chalcone

Chemical Property:

• Boiling Point: 538.7±50.0 °C(Predicted)
• PKA: 6.94±0.40(Predicted)
• PSA: 97.99000
• Density: 1.483±0.06 g/cm3(Predicted)
• LogP: 2.40510
• Storage Temp.: 2-8°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 272.06847348
• Heavy Atom Count: 20
• Complexity: 347

Purity/Quality:

96% ^*data from raw suppliers

Naringenin chalcon phyproof Reference Substance ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Naringenin chalcone

There total 28 articles about Naringenin chalcone 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: 89.0%

C19H20O7 → naringenin chalcone (25515-46-2)

Guidance literature:

With hydrogenchloride; In methanol; at 70 ℃; for 0.5h;

DOI:10.3390/molecules25173908

Reference yield: 80.0%

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on (480-41-1) → naringenin chalcone (25515-46-2)

Guidance literature:

With potassium hydroxide; In methanol; at 40 ℃; for 4h;

DOI:10.1016/j.molcatb.2013.09.009

Reference yield: 79.0%

2'-hydroxy-4,4',6'-trimethoxymethoxylchalcone (118075-12-0) → 2',4',6',4-tetrahydroxydihydrochalcone (25515-46-2,73692-50-9)

Guidance literature:

With hydrogenchloride; In methanol; at 60 ℃; for 0.25h; Reflux;

upstream raw materials:

2,4,6-trihydroxyacetophenone

4-hydroxy-benzaldehyde

p-coumaroyl-coenzyme A

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

Downstream raw materials:

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on

naringenin-4'-O-β-D-glucuronide

naringenin chalcone-2'-O-β-D-glucuronide

Refernces

• 1、 Abe, Ikuro,Watanabe, Tatsuya,Noguchi, Hiroshi. "Enzymatic formation of long-chain polyketide pyrones by plant type III polyketide synthases". . p. 2447 - 2453. Retrieved 2004.
• 2、 Choi, Jung-Won,Hwang, Ki-Chul,Jeong, Seongtae,Kim, Kundo,Kim, Sang Woo,Lee, Jiyun,Lee, Seahyoung,Lee, Yunmi,Lim, Soyeon,Oh, Sena. "Isoliquiritigenin Derivatives Inhibit RANKL-Induced Osteoclastogenesis by Regulating p38 and NF-κB Activation in RAW 264.7 Cells". supporting information. . Retrieved 2020/09/17.
• 3、 Hu, Chunling,Zhou, Zongbao,Xiang, Yuanhang,Song, Xiaoying,Wang, Hong,Tao, Kaiqi,Ye, Xiaochuan. "Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives". . p. 194 - 205. Retrieved 2018/04/19.