(2R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one

Base Information

• Chemical Name: (2R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
• CAS No.: 480-41-1
• Molecular Formula: C15H12O5
• Molecular Weight: 272.257
• Hs Code.: 29329990
• European Community (EC) Number: 207-550-2
• Nikkaji Number: J598.561G
• Wikipedia: Naringenin
• Wikidata: Q27121979
• NCI Thesaurus Code: C68463
• Metabolomics Workbench ID: 57364
• Mol file: 480-41-1.mol

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

Chemical Property of (2R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one

Chemical Property:

• Appearance/Colour: beige-brown powder
• Vapor Pressure: 6.18E-14mmHg at 25°C
• Melting Point: 247-250 °C
• Refractive Index: 1.692
• Boiling Point: 577.5°C at 760mmHg
• PKA: 7.52±0.40(Predicted)
• Flash Point: 224.7°C
• PSA: 86.99000
• Density: 1.485 g/cm³
• LogP: 2.50990
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• 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:

98% ^*data from raw suppliers

Naringenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

Useful:

• Canonical SMILES: C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
• Isomeric SMILES: C1[C@@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
• Recent ClinicalTrials: Safety and Pharmacokinetics of an Extract of Naringenin
• Uses: The aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions antiulcer, antioxidant, immunomodulator, cholesterol lowering (S)-Naringenin, an active flavanone, maintains antioxidative, anti-inflammatory and antitumorigenic activities. Used in the treatment of praquat (PQ)-induced oxidative stress.

Technology Process of (2R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one

There total 71 articles about (2R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-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: 72.0%

(2S)-naringenin 5,4'-di-O-β-D-glucopyranoside (1160434-47-8) → D-glucose (50-99-7) + naringenin (480-41-1)

Guidance literature:

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

DOI:10.1248/cpb.57.361

upstream raw materials:

(2S)-(-)-naringenin-5-O-β-D-glucopyranoside

4,2',4',6'-tetrahydroxychalchone 4'-glucoside

naringenin 7-O-(6-O-((E)-p-coumaroyl)-β-D-glucopyranoside)

(-)-(S)-sakuranetin

Downstream raw materials:

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one

(+/-)-6,8-Diprenylnaringenin

5,7,4'-trihydroxy-6-prenylflavanone

sophoraflavanone B

Refernces

• 1、 Ni, Hui,Xiao, An-Feng,Wang, Ya Qi,Chen, Feng,Cai, Hui-Nong,Su, Wen-Jun. "Development and evaluation of an HPLC method for accurate determinations of enzyme activities of naringinase complex". . p. 10026 - 10032. Retrieved 2013.
• 2、 Zapesochnaya et al.. "-". . . Retrieved 1972.
• 3、 Bornscheuer, Uwe T.,Brückner, Stephan I.,Gei?ler, Torsten,Gross, Egon,Hartmann, Beate,Ley, Jakob P.,Meinert, Hannes,R?ttger, Carsten,Schuiten, Eva,Yi, Dong,Zirpel, Bastian. "Discovery of Novel Bacterial Chalcone Isomerases by a Sequence-Structure-Function-Evolution Strategy for Enzymatic Synthesis of (S)-Flavanones". supporting information. p. 16874 - 16879. Retrieved 2021/07/06.
• 4、 -. "Flavanone compound as well as preparation method and application thereof". Paragraph 0202-0205. . Retrieved 2021/04/17.