23363-08-8

Basic information

• Product Name: b-D-Glucopyranose,1,6-bis(3,4,5-trihydroxybenzoate)
• Synonyms: Glucopyranose,1,6-digallate, b-D-(8CI); 1,6-Di-O-galloyl-b-D-glucopyranose; 1,6-Di-O-galloyl-b-D-glucose; 1,6-Digalloyl-b-D-glucose; 1,6-O-Digalloyl-b-D-glucopyranose
• CAS NO: 23363-08-8
• Molecular Formula: C20H20 O14
• Molecular Weight: 484.37
• Mol File: 23363-08-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: b-D-Glucopyranose,1,6-bis(3,4,5-trihydroxybenzoate)(CAS DataBase Reference)
• NIST Chemistry Reference: b-D-Glucopyranose,1,6-bis(3,4,5-trihydroxybenzoate)(23363-08-8)
• EPA Substance Registry System: b-D-Glucopyranose,1,6-bis(3,4,5-trihydroxybenzoate)(23363-08-8)

Safety Data

• Hazardous Substances Data: 23363-08-8(Hazardous Substances Data)

Usage

General Description

Beta-D-Glucopyranose,1,6-bis(3,4,5-trihydroxybenzoate) is a complex chemical compound that is essentially a derivative of glucopyranose. b-D-Glucopyranose,1,6-bis(3,4,5-trihydroxybenzoate) is characterized by the presence of two benzoate functional groups, which are each attached to a glucopyranose molecule by a 1,6-bis linkage. Each benzoate group is further substituted with three hydroxy groups, making them trihydroxybenzoates. b-D-Glucopyranose,1,6-bis(3,4,5-trihydroxybenzoate), owing to its multiple functional groups, exhibits a balancing mix of hydrophilic (due to hydroxy groups) and hydrophobic (due to benzoate groups) properties. However, detailed studies on its physical characteristics, potential applications, and biological activities are still limited in scientific literature.

Synthetic route

C40H28N2O20 (131959-66-5) → 1,6-di-O-galloyl-β-D-glucopyranose (23363-08-8) + 2,3-dihydroxy-chromeno[5',4',3':3,4,5]chromeno[7,8-b]quinoxaline-5,14-dione (18463-81-5)

Conditions	Yield
With water at 90℃; for 3h;

C74H52N2O42 (135326-03-3) → 1,6-di-O-galloyl-β-D-glucopyranose (23363-08-8) + isomallotinic acid (131402-64-7) + C54H44O36 (135295-57-7) + 2,3-dihydroxy-chromeno[5',4',3':3,4,5]chromeno[7,8-b]quinoxaline-5,14-dione (18463-81-5)

Conditions	Yield
With water for 30h;	A 5 mg B 2 mg C 54 mg D 14 mg

3-desgalloylterchebin (131997-74-5) → 1,6-di-O-galloyl-β-D-glucopyranose (23363-08-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 27 mg / 20 percent AcOH / ethanol / 1.5 h / Ambient temperature 2: H2O / 3 h / 90 °C View Scheme

C76H68O14 → 1,6-di-O-galloyl-β-D-glucopyranose (23363-08-8)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol; water at 40℃; under 7600.51 Torr; for 12h;	1.2 g

1,6-di-O-galloyl-β-D-glucopyranose (23363-08-8) → ellagic acid (476-66-4)

Conditions	Yield
In aq. buffer at 22℃; pH=10; Kinetics; pH-value; Time;

Upstream product

• 131959-66-5 C₄₀H₂₈N₂O₂₀ 
• 131997-74-5 3-desgalloylterchebin 
• 135326-03-3 C₇₄H₅₂N₂O₄₂ 

Downstream Products

• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 7253-25-0 6-O-galloyl-D-glucopyranose 
• 79886-49-0 1,2,6-tri-O-galloyl β-D-glucopyranoside 
• 476-66-4 ellagic acid 

Relevant articles and documents

The synthesis and antitumor activity of twelve galloyl glucosides

Twelve galloyl glucosides 1-12, showing diverse substitution patterns with two or three galloyl groups, were synthesized using commercially available, low-cost D-glucose and gallic acid as starting materials. Among them, three compounds, methyl 3,6-di-O-galloyl-?±-D-glucopyranoside (9), ethyl 2,3-di-O-galloyl-?±-D-glucopyranoside (11) and ethyl 2,3-di-O-galloyl-?2-D-glucopyranoside (12), are new compounds and other six, 1,6-di-O-galloyl-?2-D-glucopyranose (1), 1,4,6-tri-O-galloyl-?2-D-glucopyranose (2), 1,2-di-O-galloyl-?2-D-glucopyranose (3), 1,3-di-O-galloyl-?2-D-glucopyranose (4), 1,2,3-tri- O-galloyl-?±-D-glucopyranose (6) and methyl 3,4,6-tri-O-galloyl-?±-D-glucopyranoside (10), were synthesized for the first time in the present study. In in vitro MTT assay, 1-12 inhibited human cancer K562, HL-60 and HeLa cells with inhibition rates ranging from 64.2% to 92.9% at 100 ??g/mL, and their IC50 values were determined to be varied in 17.2-124.7 ??M on the tested three human cancer cell lines. In addition, compounds 1-12 inhibited murine sarcoma S180 cells with inhibition rates ranging from 38.7% to 52.8% at 100 ??g/mL in the in vitro MTT assay, and in vivo antitumor activity of 1 and 2 was also detected in murine sarcoma S180 tumor-bearing Kunming mice using taxol as positive control.

Tannins and related compounds. XCVI. Structures of macaranins and macarinins, new hydrolyzable tannins possessing macaranoyl and tergalloyl ester groups, from the leaves of Macaranga sinensis (BAILL.) MUELL.-ARG.

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