111234-34-5

Basic information

• Product Name: 1,2,3,4,6-pentakis-[O-(3,4,5-trimethoxybenzoyl)]-α-D-glucopyranose
• Synonyms: 1,2,3,4,6-pentakis-[O-(3,4,5-trimethoxybenzoyl)]-α-D-glucopyranose
• CAS NO: 111234-34-5
• Molecular Weight: 1151.09
• Mol File: 111234-34-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,2,3,4,6-pentakis-[O-(3,4,5-trimethoxybenzoyl)]-α-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,6-pentakis-[O-(3,4,5-trimethoxybenzoyl)]-α-D-glucopyranose(111234-34-5)
• EPA Substance Registry System: 1,2,3,4,6-pentakis-[O-(3,4,5-trimethoxybenzoyl)]-α-D-glucopyranose(111234-34-5)

Safety Data

• Hazardous Substances Data: 111234-34-5(Hazardous Substances Data)

Upstream product

• 2280-44-6 D-Glucose 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 118-41-2 Eudesmic acid 
• 81956-07-2 nupharin A 
• 186581-53-3 diazomethane 
• 70470-10-9 1,2,3,4,6-Penta-O-galloyl-alpha-D-glucopyranose 

Relevant articles and documents

Anomeric selectivity and influenza A virus inhibition study on methoxylated analogues of Pentagalloylglucose

Anomeric selectivity in galloylation of d-glucose and d-mannose with carboxylic acid was explored under steglich conditions. Base catalyst 4-dimethylaminopyridine favored the formation of alpha-anomers, while adding an acid and carbodiimide favored the formation of beta-anomers. Steric hindrance between α,β-unsaturated acid and C-2 OH stereochemistry (adjacent carbon to anomeric) influenced anomeric selectivity for both d-glucose and d-mannose. The influenza A virus inhibition activities of the synthesized compounds were evaluated in Madin-Darby canine kidney cell line using the cytopathic effect inhibition assay. All the synthetic methoxylated analogues showed more considerable activity against influenza A virus than their corresponding acids, which indicated the sugar core as key functionality for anti-viral activity. The activities of trimethoxy-cinnamic acid Pentagalloylglucose analogues, 3α, 3β, 4α, and 4β (IC50, 109.1 μM, 134.4 μM, 119.5 μM, 111.1 μM, respectively) were better than those of trimethoxy-benzoic acid Pentagalloylglucose analogues, 1-αβ and 2α, 2β (IC50, 209.8 μM, 132.9 μM, 161.2 μM, respectively), which suggested that the double bond in cinnamic acid Pentagalloylglucose analogues makes the major contribution for influenza A virus inhibitory activity. Notably, several anomeric mixtures showed better activities than pure alpha or beta anomer and were almost two times more effective than Ribavirin, a clinically used anti-viral drug.

Tannins and Related Compounds. LVIII. Novel Gallotannins Possessing an α-Glucose Core from Nuphar japonicum DC.

Together with 6-O- and 2,3,4,6-tetra-O-galloylglucoses, two unusual gallotannis possessing an α-D-glucopyranose core have been isolated from the rhizomes of Nuphar japonicum DC. (Nymphaeaceae), and their structures have been established as 1,2,4-tri-O-galloyl-α-D-glucose (3) and 1,2,3,4,6-penta-O-galloyl-α-D-glucose (6) on the basis of chemical and spectroscopic evidence.KEYWORDS---Nuphar japonicum; Nimphaeaceae; hydrolizable tannin; gallotannin; α-glucose; gallic acid; HPLC