(+/-)-Naringenin

Base Information

• Chemical Name: (+/-)-Naringenin
• CAS No.: 93602-28-9
• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.257
• Mol file: 93602-28-9.mol

Synonyms:(+/-)-4',5,7-Trihydroxyflavanone;

Chemical Property of (+/-)-Naringenin

Chemical Property:

• Melting Point: 247-250 °C(lit.)
• Boiling Point: 577.5 °C at 760 mmHg
• Flash Point: 224.7 °C
• PSA: 86.99000
• Density: 1.485 g/cm³
• LogP: 2.50990

Purity/Quality:

98%,99%, ^*data from raw suppliers

(+/-)-Naringenin 98% ^*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

Useful:

Technology Process of (+/-)-Naringenin

There total 4 articles about (+/-)-Naringenin 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.