387372-17-0

Basic information

• Product Name: trans Resveratrol 3-O-b-D-Glucuronide
• Synonyms: 3-Hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl b-D-Glucopyranosiduronic Acid;Resveratrol 3-O-Glucuronide;trans Resveratrol 3-O-b-D-Glucuronide;3-Hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl -D-Glucopyranosiduronic Acid;trans Resveratrol 3-O--D-Glucuronide;Resveratrol 3-O-D-Glucuronide;3-Hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl
• CAS NO: 387372-17-0
• Molecular Formula: C20H20O9
• Molecular Weight: 404.3674
• Product Categories: Inhibitors;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 387372-17-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: >150?C (dec.)
• Boiling Point: 758.065°C at 760 mmHg
• Flash Point: 271.616°C
• Appearance: /
• Density: 1.616g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.76
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: trans Resveratrol 3-O-b-D-Glucuronide(CAS DataBase Reference)
• NIST Chemistry Reference: trans Resveratrol 3-O-b-D-Glucuronide(387372-17-0)
• EPA Substance Registry System: trans Resveratrol 3-O-b-D-Glucuronide(387372-17-0)

Safety Data

• Hazardous Substances Data: 387372-17-0(Hazardous Substances Data)

Usage

Description

Resveratrol is a potent phenolic antioxidant found in grapes and red wine that also has antiproliferative and anti-inflammatory activity. In humans, resveratrol is almost completely conjugated to its glucuronide and sulfate metabolites. trans-Resveratrol-3-O-β-D-glucuronide is a regioisomeric resveratrol metabolite that may be used as a reference standard for accurate determination of the metabolic profile of resveratrol.

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 387372-17-0 differently. You can refer to the following data:
1. Resveratrol is a potent phenolic antioxidant found in grapes and red wine that also has antiproliferative and anti-inflammatory activity. In humans, resveratrol is almost completely conjugated to its glucuronide and sulfate metabolites. trans-Resveratrol-3-O-β-D-glucuronide is a regioisomeric resveratrol metabolite that may be used as a reference standard for accurate determination of the metabolic profile of resveratrol.
2. A metabolite of trans Resveratrol (R150000).

InChI:InChI=1/C20H20O9/c21-12-5-3-10(4-6-12)1-2-11-7-13(22)9-14(8-11)28-20-17(25)15(23)16(24)18(29-20)19(26)27/h1-9,15-18,20-25H,(H,26,27)/b2-1+/t15-,16-,17-,18?,20+/m0/s1

Upstream product

• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 1245697-26-0 UDP-glucuronic acid 
• 827348-01-6 (E)-1-{[3-tert-butyl(dimethyl)silyl]oxy}-5-hydroxyphenyl-2-({[4-tert-butyl(dimethyl)silyl]oxy}-phenyl)ethene 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 490028-22-3 (E)-1-(3-acetoxy-5-(2,3,4-triacetyl-β-D-glucuronopyranosido)phenyl)-2-(4'-acetoxyphenyl)ethene methyl ester 
• 861446-14-2 (E)-4-(3-acetoxy-5-hydroxystyryl)phenyl acetate 
• 42206-94-0 triacetyl-trans-resveratrol 
• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 108957-75-1 diethyl 3,5-dimethoxybenzylphosphonate 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 6652-32-0 3,5-dimethoxybenzylchloride 
• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 827026-54-0 C₂₇H₂₈O₁₂ 

Relevant articles and documents

Influence of glucuronidation and reduction modifications of resveratrol on its biological activities

Resveratrol (3,5,4′-trihydroxystilbene, RES), a star among dietary polyphenols, shows a wide range of biological activities, but it is rapidly and extensively metabolized into its glucuronide and sulfate conjugates as well as to the corresponding reduced

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.

A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol

A simple and direct strategy to chemically synthesize O-β-d-glucuronides of urolithin-B 4, resveratrol 5, and the corresponding hydroxytyrosol derivatives 6, 7 (as a regioisomeric mixture), and 8 is described. The critical glycosylation step has been opti