5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one

Base Information

• Chemical Name: 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
• CAS No.: 67604-48-2
• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.257
• Hs Code.: 29329990
• European Community (EC) Number: 266-769-1
• NSC Number: 34875,11855
• DSSTox Substance ID: DTXSID50274239
• Nikkaji Number: J6.165D
• Wikipedia: Naringenin
• Wikidata: Q57826857
• NCI Thesaurus Code: C68463
• Pharos Ligand ID: 8RQVTSKSGC6C
• Metabolomics Workbench ID: 130884
• ChEMBL ID: CHEMBL32571
• Mol file: 67604-48-2.mol

Synonyms:(2S)-naringenin;4',5,7-trihydroxyflavanone;BE 14348A;BE-14348A;naringenin;naringenin-7-sulfate

Chemical Property of 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one

Chemical Property:

• Melting Point: 247-250oC(lit.)
• Boiling Point: 577.5°Cat760mmHg
• PKA: 7.52±0.40(Predicted)
• Flash Point: 224.7°C
• PSA: 83.83000
• Density: 1.485g/cm³
• LogP: 2.13750
• Storage Temp.: 0-6°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in ethanol (50 mg/ml), DMSO, methanol, and ammonium hydroxide (50 mg/ml). Insoluble in water (almost)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 272.06847348
• Heavy Atom Count: 20
• Complexity: 363

Purity/Quality:

racNaringenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
• Recent ClinicalTrials: Safety and Pharmacokinetics of an Extract of Naringenin
• Uses: A PI 3-kinase inhibitor. The aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions.

Technology Process of 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one

There total 4 articles about 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one 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: 73.0%

(2S)-naringenin 5-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside (1160434-44-5) → D-glucose (50-99-7) + (+)-Naringenin (480-41-1,17654-19-2,67604-48-2,93602-28-9)

Guidance literature:

With hydrogenchloride; water; at 80 ℃; for 1h;

DOI:10.1248/cpb.57.361

Reference yield: 73.0%

(2R)-naringenin 5-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside → D-glucose (50-99-7) + (+)-Naringenin (480-41-1,17654-19-2,67604-48-2,93602-28-9)

Guidance literature:

With hydrogenchloride; water; at 80 ℃; for 1h;

DOI:10.1248/cpb.57.361

Reference yield:

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on (480-41-1) → naringenin (480-41-1) + (+)-Naringenin (480-41-1,17654-19-2,67604-48-2,93602-28-9)

Guidance literature:

Resolution of racemate;

DOI:10.1021/jo8014165

upstream raw materials:

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

(2S)-naringenin 5-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside

naringenin chalcone

Downstream raw materials:

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

kaempferol

(2S,3S)-3,40,5,7-tetrahydroxyflavanone

(2R,3S)-dihydrokaempferol

Refernces

• 1、 Bouanini, Meriem,Belboukhari, Nasser,Menéndez, J. Carlos,Sekkoum, Khaled,Cheriti, Abdelkarim,Aboul-Enein, Hassan Y.. "Chiral separation of novel iminonaringenin derivatives". . p. 484 - 490. Retrieved 2018/04/02.
• 2、 Curti, Valeria,Di Lorenzo, Arianna,Rossi, Daniela,Martino, Emanuela,Capelli, Enrica,Collina, Simona,Daglia, Maria. "Enantioselective modulatory effects of naringenin enantiomers on the expression levels of miR-17-3p involved in endogenous antioxidant defenses". . . Retrieved 2017/03/11.