Naringenin 7-O-glucuronide

Base Information

• Chemical Name: Naringenin 7-O-glucuronide
• CAS No.: 158196-34-0
• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.383
• DSSTox Substance ID: DTXSID60573866
• Metabolomics Workbench ID: 49522
• Nikkaji Number: J575.880G
• Wikidata: Q72493890
• Mol file: 158196-34-0.mol

Synonyms:158196-34-0;naringenin-7-o-beta-d-glucuronide;Naringenin 7-O-beta-D-glucuronide;(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxane-2-carboxylic acid;Naringenin-7-O-glucuronide;Naringenin 7-O-glucuronide;(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(((S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxochroman-7-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid;DTXSID60573866;HY-N2066;AKOS040760583;FS-10628;PD044321;CS-0018571

Chemical Property of Naringenin 7-O-glucuronide

Chemical Property:

• Boiling Point: 855.1±65.0 °C(Predicted)
• PKA: 2.74±0.70(Predicted)
• PSA: 183.21000
• Density: 1.688±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 0.07530
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 448.10056145
• Heavy Atom Count: 32
• Complexity: 693

Purity/Quality:

95%-98% ^*data from raw suppliers

Naringenin 7-O-β-D-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC2=CC(=CC(=C2C1=O)O)OC3C(C(C(C(O3)C(=O)O)O)O)O)C4=CC=C(C=C4)O
• Isomeric SMILES: C1[C@H](OC2=CC(=CC(=C2C1=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O)C4=CC=C(C=C4)O
• Uses: A metabolite of Naringenin (N378950).

Technology Process of Naringenin 7-O-glucuronide

There total 7 articles about Naringenin 7-O-glucuronide 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: 30.0%

4',5-di-O-benzoylnaringenin 7-O-[methyl (2'',3'',4''-tri-O-acetyl)-β-D-glucopyranosyl uronate] (1237479-02-5) → naringenin-7-O-β-D-glucuronopyranoside (158196-34-0)

Guidance literature:

4',5-di-O-benzoylnaringenin 7-O-[methyl (2'',3'',4''-tri-O-acetyl)-β-D-glucopyranosyl uronate]; With water; sodium carbonate; at 0 - 20 ℃; for 5h; Inert atmosphere;

In water; pH=Ca. 6; Inert atmosphere;

DOI:10.1021/jf1010403

Reference yield:

naringenin chalcone (25515-46-2) + UDP-glucuronic acid (1245697-26-0,106864-00-0,14520-48-0,30329-32-9,3545-73-1,5918-40-1) → naringenin-4'-O-β-D-glucuronide (158196-35-1) + naringenin chalcone-2'-O-β-D-glucuronide (1174375-93-9) + Naringenin 7-O-glucuronide (158196-34-0)

Guidance literature:

With magnesium chloride; In ethanol; water; at 25 ℃; for 3h; pH=5; aq. HEPES buffer; Enzymatic reaction;

DOI:10.1021/jf901137x

Reference yield:

uridine 5'-diphosphoglucuronic acid trisodium salt + naringenin (480-41-1) → naringenin 7-O-glucuronide (158196-34-0)

Guidance literature:

With human UDP-glucuronosyltransferase UGT₁A₉; In methanol; water; at 37 ℃; pH=7; regioselective reaction; phosphate buffer; Enzymatic reaction;

DOI:10.1016/j.bcp.2011.08.015

upstream raw materials:

naringenin chalcone

UDP-glucuronic acid

4',5-di-O-benzoylnaringenin

4',5-di-O-benzoylnaringenin 7-O-[methyl (2'',3'',4''-tri-O-acetyl)-β-D-glucopyranosyl uronate]