trans-Resveratrol 3-O-glucuronide

Base Information

• Chemical Name: trans-Resveratrol 3-O-glucuronide
• CAS No.: 387372-17-0
• Molecular Formula: C₂₀H₂₀O₉
• Molecular Weight: 404.373
• Hs Code.: 2938909090
• UNII: LNK7Z424CK
• ChEMBL ID: CHEMBL3526289
• DSSTox Substance ID: DTXSID20693973
• Metabolomics Workbench ID: 49532
• Nikkaji Number: J2.186.237A
• Wikidata: Q3491489
• Wikipedia: Trans-Resveratrol-3-O-glucuronide
• Mol file: 387372-17-0.mol

Synonyms:387372-17-0;trans-Resveratrol 3-O-glucuronide;Trans-Resveratrol-3-O-glucuronide;Resveratrol 3-O-Glucuronide;LNK7Z424CK;trans-Resveratrol 3-glucuronide;UNII-LNK7Z424CK;trans-Resveratrol-3-o-beta-D-glucuronide;Resveratrol-3-o-beta-D-glucuronide, trans-;(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]oxane-2-carboxylic acid;trans-Resveratrol 3-O-beta-D-Glucuronide;3-Hydroxy-5-((1E)-2-(4-hydroxyphenyl)ethenyl)phenyl beta-D-glucopyranosiduronic acid;beta-D-Glucopyranosiduronic acid, 3-hydroxy-5-((1E)-2-(4-hydroxyphenyl)ethenyl)phenyl;(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxane-2-carboxylic acid;Resveratrol metabolite 2;CHEMBL3526289;SCHEMBL21176631;DTXSID20693973;CHEBI:175990;trans-Resveratrol 3-O-?-D-Glucuronide;PD021151;NS00116297;Q3491489;.beta.-D-Glucopyranosiduronic acid, 3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenyl;(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(3-hydroxy-5-((E)-4-hydroxystyryl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid;(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)vinyl]phenoxy]tetrahydropyran-2-carboxylic acid;.BETA.-D-GLUCOPYRANOSIDURONIC ACID, 3-HYDROXY-5-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)PHENYL;3-HYDROXY-5-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)PHENYL .BETA.-D-GLUCOPYRANOSIDURONIC ACID

Chemical Property of trans-Resveratrol 3-O-glucuronide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >150?C (dec.)
• Refractive Index: 1.76
• Boiling Point: 758.065°C at 760 mmHg
• Flash Point: 271.616°C
• PSA: 156.91000
• Density: 1.616g/cm³
• LogP: 0.53920
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 404.11073221
• Heavy Atom Count: 29
• Complexity: 574

Purity/Quality:

98%Min ^*data from raw suppliers

trans-Resveratrol 3-O-b-D-glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC2=CC(=CC(=C2)OC3C(C(C(C(O3)C(=O)O)O)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O)O)O
• 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.
• Uses: 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. A metabolite of trans Resveratrol (R150000).

Technology Process of trans-Resveratrol 3-O-glucuronide

There total 15 articles about trans-Resveratrol 3-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: 83.0%

C27H28O12 (827026-54-0) → Resveratrol-3-O-glucuronide (387372-17-0)

Guidance literature:

With water; sodium carbonate; In methanol; at 20 ℃; for 16h;

DOI:10.1016/j.carres.2009.05.016

Reference yield:

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → resveratrol-3-O-glucuronide (387372-17-0) + resveratrol-4'-O-glucuronide

Guidance literature:

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol; 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester; With sodium; In methanol; at 20 ℃; for 2h;

With methanol; sodium hydroxide; for 2h; Reflux;

With hydrogenchloride; In methanol; water; ethyl acetate;

DOI:10.1016/j.bmcl.2009.09.114

Reference yield:

ethyl 3,5-dimethoxybenzoate (17275-82-0) → Resveratrol-3-O-glucuronide (387372-17-0)

Guidance literature:

Multi-step reaction with 9 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2: hydrogenchloride / water / Inert atmosphere

3: 10 h / 140 °C / Inert atmosphere

4: potassium hydroxide / tetrahydrofuran / 24 h / Inert atmosphere

5: magnesium; methyl iodide / diethyl ether / 45 - 190 °C / Inert atmosphere

6: triethylamine / dichloromethane / 4 h / Inert atmosphere

7: ammonium acetate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere

8: boron trifluoride diethyl etherate / dichloromethane / 1.58 h / -10 °C / Inert atmosphere

9: water; sodium hydroxide / methanol / Inert atmosphere

With hydrogenchloride; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; ammonium acetate; water; magnesium; triethylamine; potassium hydroxide; sodium hydroxide; methyl iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 3: |Arbuzov Reaction;

DOI:10.1080/00397911.2011.585733

upstream raw materials:

C₂₇H₂₈O₁₂

ethyl 3,5-dimethoxybenzoate

3,5-dimethoxybenzylchloride

3,5-dimethoxybenzyl alcohol

Refernces

• 1、 Biasutto, Lucia,Marotta, Ester,Bradaschia, Alice,Fallica, Mauro,Mattarei, Andrea,Garbisa, Spiridione,Zoratti, Mario,Paradisi, Cristina. "Soluble polyphenols: Synthesis and bioavailability of 3,4′,5-tri(α-d-glucose-3-O-succinyl) resveratrol". . p. 6721 - 6724. Retrieved 2009.
• 2、 Wu, Baojian,Wang, Xiaoqiang,Zhang, Shuxing,Hu, Ming. "Accurate prediction of glucuronidation of structurally diverse phenolics by human UGT1A9 using combined experimental and in silico approaches". experimental part. p. 1544 - 1561. Retrieved 2012/07/27.