158196-34-0

Basic information

• Product Name: Naringenin 7-O-β-D-Glucuronide (Mixture of Diastereomers)
• Synonyms: Naringenin 7-O-β-D-Glucuronide (Mixture of Diastereomers);Naringenin-7-O-glucuronide;(2S)-3,4-Dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid;Naringenin 7-O-beta-D-glucuronide;Naringenin-7-O-beta-D-glucuronide min. 98%
• CAS NO: 158196-34-0
• Molecular Formula: C21H20O11
• Molecular Weight: 448.3769
• Product Categories: Aromatics;Glucuronide;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 158196-34-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 855.1±65.0 °C(Predicted)
• Appearance: /
• Density: 1.688±0.06 g/cm3 (20 ºC 760 Torr)
• PKA: 2.74±0.70(Predicted)
• CAS DataBase Reference: Naringenin 7-O-β-D-Glucuronide (Mixture of Diastereomers)(CAS DataBase Reference)
• NIST Chemistry Reference: Naringenin 7-O-β-D-Glucuronide (Mixture of Diastereomers)(158196-34-0)
• EPA Substance Registry System: Naringenin 7-O-β-D-Glucuronide (Mixture of Diastereomers)(158196-34-0)

Safety Data

• Hazardous Substances Data: 158196-34-0(Hazardous Substances Data)

Usage

Uses

A metabolite of Naringenin (N378950).

Upstream product

• 25515-46-2 naringenin chalcone 
• 1245697-26-0 UDP-glucuronic acid 
• 41350-12-3 4',5-di-O-benzoylnaringenin 
• 1237479-02-5 4',5-di-O-benzoylnaringenin 7-O-[methyl (2'',3'',4''-tri-O-acetyl)-β-D-glucopyranosyl uronate] 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 125130-59-8 4',5,7-tri-O-benzoylnaringenin 
• 480-41-1 naringenin 

Relevant articles and documents

Regioselectivity of human UDP-glucuronosyltransferase isozymes in flavonoid biotransformation by metal complexation and tandem mass spectrometry

Based on reactions with five flavonoids, the regioselectivities of twelve human UDP-glucuronosyltransferase (UGT) isozymes were elucidated. The various flavonoid glucuronides were differentiated based on LC-MS/MS fragmentation patterns of [Co(II)(flavonoid-H)(4,7-diphenyl-1,10-phenanthroline) 2]+ complexes generated upon post-column complexation. Glucuronide distributions were evaluated to allow a systematic assessment of the regioselectivity of each isozyme. The various UGT enzymes, including eight UGT1A and four UGT2B, displayed a remarkable range of selectivities, both in terms of the positions of glucuronidation and relative reactivity with flavanones versus flavonols.

Chemical synthesis of citrus Flavanone glucuronides

Flavanone glucuronides are the major phenolic metabolites detected in human plasma after consumption of citrus fruits. As such, they might display significant cardioprotective effects. In this work, glucuronides of naringenin (4′- and 7-O-β-d-glucuronides