Piceatannol 3'-O-glucoside

Base Information

• Chemical Name: Piceatannol 3'-O-glucoside
• CAS No.: 94356-26-0
• Molecular Formula: C20H22O9
• Molecular Weight: 406.389
• Mol file: 94356-26-0.mol

Synonyms:Piceatannol 3'-O-glucoside;Quzhaqigan;Piceatannol 3'-O-beta-D-glucopyranoside

Chemical Property of Piceatannol 3'-O-glucoside

Chemical Property:

• Boiling Point: 721.6±60.0 °C(Predicted)
• PKA: 9.16±0.10(Predicted)
• PSA: 160.07000
• Density: 1.593±0.06 g/cm3(Predicted)
• LogP: 0.15250
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)

Purity/Quality:

≥98% ^*data from raw suppliers

Piceatannol3''-O-Glucoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Piceatannol 3''-O-Glucoside, is an active component of Rhubarb, activates endothelial nitric oxide (NO) synthase through inhibition of arginase activity with IC50 value of 11.22 μM and 11.06 μM against arginase I and arginase II, respectively.

Technology Process of Piceatannol 3'-O-glucoside

There total 13 articles about Piceatannol 3'-O-glucoside 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: 65.0%

3,5,4′-triacetoxy-3′-hydroxystilbene-3′-O-β-D-(2,3,4,6-tetra-O-acetyl)glucopyranoside → piceatannol 3'-O-β-D-glucopyranoside (94356-26-0)

Guidance literature:

With methanol; sodium methylate; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1055/a-1639-0648

Reference yield:

piceatannol 3-O-β-D-(6''-O-galloyl) glucopyranoside (94356-28-2) → 3,4,5-trihydroxybenzoic acid (149-91-7) + piceatannol 3'-O-β-D-glucopyranoside (94356-26-0)

Guidance literature:

With tannase; In water; for 0.5h; Ambient temperature;

Reference yield:

3,5-Dihydroxybenzoic acid (99-10-5) → piceatannol 3'-O-β-D-glucopyranoside (94356-26-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: thionyl chloride / 1 h / 0 °C / Reflux; Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / Inert atmosphere

5.2: 4 h / -78 - 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

8.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 18 h / 60 °C / Inert atmosphere

8.2: 2 h / 0 °C / Inert atmosphere

9.1: methanol; sodium methylate / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; methanol; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; sodium methylate; palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 5.2: |Wittig Olefination / 8.1: |Heck Reaction;

DOI:10.1055/a-1639-0648

upstream raw materials:

piceatannol 3-O-β-D-(6''-O-galloyl) glucopyranoside

3,5-Dihydroxybenzoic acid

1-carbomethoxy-3,5-dihydroxybenzene

methyl 3,5-bis(tert-butyldimethylsilyloxy)benzoate

Downstream raw materials:

5-[(2E)-(3,5-dihydroxyphenyl)vinyl]-2-methoxyphenyl-1-O-β-D-glucopyranoside

D-Glucose

trans-piceatannol