387372-17-0

Usage

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

• 827026-54-0 C₂₇H₂₈O₁₂ 
• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 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 
• 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 

Relevant academic research and scientific papers

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

Soluble polyphenols: Synthesis and bioavailability of 3,4′,5-tri(α-d-glucose-3-O-succinyl) resveratrol

We report the development of a chemical modification method of general applicability to polyphenols, which increases solubility to influence absorption. Glucosyl groups were added to the resveratrol kernel via a succinate linker, yielding 3,4′,5-tri-(α-d-

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.

Practical preparation of resveratrol 3-O-β-D-glucuronide

A practical synthesis of resveratrol 3-Oβl-D-glucuronide, suitable for preparation of large quantities, was developed using selective deacetylation of resveratrol triacetate with ammonium acetate. A simplified procedure for large-scale preparation of resveratrol is also reported.

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