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

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

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

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.

Accurate prediction of glucuronidation of structurally diverse phenolics by human UGT1A9 using combined experimental and in silico approaches

Purpose: Catalytic selectivity of human UGT1A9, an important membrane-bound enzyme catalyzing glucuronidation of xenobiotics, was determined experimentally using 145 phenolics and analyzed by 3D-QSAR methods. Methods: Catalytic efficiency of UGT1A9 was determined by kinetic profiling. Quantitative structure activity relationships were analyzed using CoMFA and CoMSIA techniques. Molecular alignment of substrate structures was made by superimposing the glucuronidation site and its adjacent aromatic ring to achieve maximal steric overlap. For a substrate with multiple active glucuronidation sites, each site was considered a separate substrate. Results: 3D-QSAR analyses produced statistically reliable models with good predictive power (CoMFA: q 2=0.548, r2=0.949, r pred 2 =0.775; CoMSIA: q2=0.579, r2=0.876, rpred2 =0.700). Contour coefficient maps were applied to elucidate structural features among substrates that are responsible for selectivity differences. Contour coefficient maps were overlaid in the catalytic pocket of a homology model of UGT1A9, enabling identification of the UGT1A9 catalytic pocket with a high degree of confidence. Conclusion: CoMFA/CoMSIA models can predict substrate selectivity and in vitro clearance of UGT1A9. Our findings also provide a possible molecular basis for understanding UGT1A9 functions and substrate selectivity.

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

Identification and quantification of metabolites of orally administered naringenin chalcone in rats

Naringenin chalcone is the main active component of tomato skin extract, which has an antiallergic activity. In this study, naringenin chalcone was orally administered to rats, and the chemical structures and levels of the major metabolites in the plasma