94356-26-0

Basic information

• Product Name: Piceatannol 3'-O-glucoside
• Synonyms: Piceatannol 3'-O-glucoside;Quzhaqigan;Piceatannol 3'-O-beta-D-glucopyranoside
• CAS NO: 94356-26-0
• Molecular Formula: C₂₀H₂₂O₉
• Molecular Weight: 406.38328
• Mol File: 94356-26-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 721.6±60.0 °C(Predicted)
• Appearance: /
• Density: 1.593±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• PKA: 9.16±0.10(Predicted)
• CAS DataBase Reference: Piceatannol 3'-O-glucoside(CAS DataBase Reference)
• NIST Chemistry Reference: Piceatannol 3'-O-glucoside(94356-26-0)
• EPA Substance Registry System: Piceatannol 3'-O-glucoside(94356-26-0)

Safety Data

• Hazardous Substances Data: 94356-26-0(Hazardous Substances Data)

Usage

Description

Piceatannol 3'-O-glucoside is a bioactive compound found in Rhubarb, known for its ability to activate endothelial nitric oxide (NO) synthase by inhibiting arginase activity. It exhibits potent inhibitory effects against arginase I and arginase II with IC50 values of 11.22 μM and 11.06 μM, respectively.

Uses

Used in Pharmaceutical Industry:
Piceatannol 3'-O-glucoside is used as a therapeutic agent for promoting endothelial nitric oxide (NO) production, which plays a crucial role in various physiological processes, including vasodilation, platelet aggregation, and neurotransmission. Its ability to inhibit arginase activity makes it a potential candidate for the treatment of cardiovascular diseases and other conditions related to NO dysregulation.
Used in Nutraceutical Industry:
Piceatannol 3'-O-glucoside is used as a dietary supplement for enhancing vascular health and promoting overall well-being. Its NO-boosting properties can contribute to improved blood flow, reduced inflammation, and better cardiovascular function.
Used in Cosmetic Industry:
Piceatannol 3'-O-glucoside is used as an active ingredient in skincare products for its potential anti-aging and skin health benefits. Piceatannol 3'-O-glucoside's ability to modulate nitric oxide levels may contribute to improved skin elasticity, reduced wrinkles, and enhanced skin barrier function.

Upstream product

• 94356-28-2 piceatannol 3-O-β-D-(6''-O-galloyl) glucopyranoside 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 103929-83-5 methyl 3,5-bis(tert-butyldimethylsilyloxy)benzoate 
• 83-87-4 D-glucose pentaacetate 
• 103929-84-6 [3,5-di(tert-butyldimethylsilanyloxy)phenyl]methanol 
• 187803-40-3 3,5-bis(tert-butyldimethylsilyloxy)benzaldehyde 
• 113231-14-4 1,3-dihydroxy-5-vinylbenzene 
• 155222-48-3 5-vinyl-1,3-phenylene diacetate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 91364-06-6 ortho-hydroxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 2280-44-6 D-Glucose 
• 10083-24-6 trans-piceatannol 
• 94356-22-6 5-[(2E)-(3,5-dihydroxyphenyl)vinyl]-2-methoxyphenyl-1-O-β-D-glucopyranoside 

Relevant articles and documents

Scalable Total Synthesis of Piceatannol-3′-O-β-d-glucopyranoside and the 4′-Methoxy Congener Thereof: An Early Stage Glycosylation Strategy

Scalable syntheses of piceatannol-3'-O-β-D-glucopyranoside and the 4'-methoxy congener thereof were achieved. This route features an early implemented Fischer-like glycosylation reaction, a regioselective iodination of phenolic glycoside under strongly acidic conditions, a highly telescoped route to access the styrene derivative, and a key Mizoroki.Heck reaction to render the desired coupled products in high overall yield.