132023-50-8

Basic information

• Product Name: 1,2,3,4-tetrakis-O-(3,4,5-trihydroxybenzoyl)-alpha-D-glucopyranose
• CAS NO: 132023-50-8
• Molecular Formula: C₃₄H₂₈O₂₂
• Molecular Weight: 788.5729
• Mol File: 132023-50-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 1238.9°C at 760 mmHg
• Flash Point: 388.1°C
• Density: 2.02g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.849
• CAS DataBase Reference: 1,2,3,4-tetrakis-O-(3,4,5-trihydroxybenzoyl)-alpha-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-tetrakis-O-(3,4,5-trihydroxybenzoyl)-alpha-D-glucopyranose(132023-50-8)
• EPA Substance Registry System: 1,2,3,4-tetrakis-O-(3,4,5-trihydroxybenzoyl)-alpha-D-glucopyranose(132023-50-8)

Safety Data

• Hazardous Substances Data: 132023-50-8(Hazardous Substances Data)

Usage

Molecular weight

862.72 g/mol

Structure

Four 3,4,5-trihydroxybenzoyl groups attached to a D-glucopyranose sugar molecule

Class

Polyphenolic compound

+ Antioxidant

Scavenges free radicals and protects cells from oxidative stress, potentially reducing the risk of chronic diseases such as cardiovascular disease and cancer.

+ Anti-inflammatory

Reduces inflammation and swelling in the body.

Potential applications

+ Pharmaceutical development for various health benefits.
+ Nutraceutical development for various health benefits.

Relevant articles and documents

Synthesis and structure-activity relationship study of antidiabetic penta-O-galloyl-D-glucopyranose and its analogues

The rapid increase of obesity-associated diabetes has created urgent demands for more effective antidiabetic therapies and pharmaceuticals that are able to address the problems of hyperglycemia and weight gain simultaneously. Our previous studies indicated that the α- and β-anomers of penta-O-galloyl-D-glucopyranose (PGG), 2 and 3, act as insulin mimetics that bind to and activate the insulin receptor, stimulate glucose transport in adipocytes, and reduce blood glucose and insulin levels in diabetic and obese animals. In addition, they inhibit differentiation of preadipocytes into adipocytes. These activities suggest that 2 and 3 may reduce blood glucose without increasing adiposity. To investigate the structure-activity relationship of 2 and 3, four series of novel compounds were prepared and their glucose transport stimulatory activities were measured using a radioactive glucose uptake bioassay. The assay results indicate that both the glucose and the galloyl groups are critical to the activity of 2 and 3. It appears that the glucose core provides an optimal scaffold to present the galloyl groups with the correct spatial orientation to induce activity. Moreover, the galloyl groups linked to the 1, 2, 3, and 4 positions of glucose are essential, while the galloyl group connected to the 6 position of 2 is unnecessary for the induction of activity. The discovery that two related novel compounds, 6-deoxytetra-O-galloyl-α-D-glucopyranose (43) and tetra-O-galloyl-α- D-xylopyranose (59), also possess glucose transport stimulatory activity suggests that 2 may be further modified around position 6 to modulate and enhance its efficacy. To test this hypothesis, we developed a new synthetic method that allows for the stereoselective preparation of derivatives of 2 that are modified on C-6. We found that 6-chloro-6-deoxy-1,2,3,4-tetra-O-galloyl- α-D-glucopyranose (80) exhibits a significantly higher glucose transport stimulatory activity than 2. Its activity is comparable to that of insulin.