R-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one

Base Information

• Chemical Name: R-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one
• CAS No.: 17654-19-2
• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.257
• Mol file: 17654-19-2.mol

Synonyms:

Chemical Property of R-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one

Chemical Property:

• Boiling Point: 577.5±50.0 °C(Predicted)
• PKA: 7.52±0.40(Predicted)
• PSA: 86.99000
• Density: 1.485±0.06 g/cm3(Predicted)
• LogP: 2.50990
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly, Sonicated)

Purity/Quality:

98%min ^*data from raw suppliers

(2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (R)-Naringenin is an active flavanone that has been studied as an inhibitor of cytochromes P450 (CYPs), specifically shown to be potent against CYP2C9 and CYP3A. It is found in grape juice as rac Naringenin (N378950) where the (S)-Naringenin (N378955) displays antioxidative, anti-inflammatory and antitumorigenic activities used in the treatment of praquat (PQ)-induced oxidative stress.

Technology Process of R-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one

There total 4 articles about R-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-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、 Gaggeri, Raffaella,Rossi, Daniela,Daglia, Maria,Leoni, Flavio,Avanzini, Maria Antonia,Mantelli, Melissa,Juza, Markus,Collina, Simona. "An eco-friendly enantioselective access to (R)-naringenin as inhibitor of proinflammatory cytokine release". . p. 1531 - 1538. Retrieved 2013.
• 2、 Nesterov, Volodymyr V.,Zakharov, Lev N.,Nesterov, Vladimir N.,Calderon, Jose G.,Longo, Antonella,Zaman, Khadiza,Choudhury, Feroza Kaneez,Farrell, William,Shulaev, Vladimir,Richmond, Michael G.. "5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one (naringenin): X-ray diffraction structures of the naringenin enantiomers and DFT evaluation of the preferred ground-state structures and thermodynamics for racemization". . p. 994 - 1000. Retrieved 2017.
• 3、 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.