1420045-11-9

Basic information

• Product Name: 3-O-[(3″,4″,5″-tri-O-methoxymethyl)-galloyl]quercetin
• Synonyms: 3-O-[(3″,4″,5″-tri-O-methoxymethyl)-galloyl]quercetin
• CAS NO: 1420045-11-9
• Molecular Weight: 586.506
• Mol File: 1420045-11-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-O-[(3″,4″,5″-tri-O-methoxymethyl)-galloyl]quercetin(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-[(3″,4″,5″-tri-O-methoxymethyl)-galloyl]quercetin(1420045-11-9)
• EPA Substance Registry System: 3-O-[(3″,4″,5″-tri-O-methoxymethyl)-galloyl]quercetin(1420045-11-9)

Safety Data

• Hazardous Substances Data: 1420045-11-9(Hazardous Substances Data)

Upstream product

• 153-18-4 rutin 
• 116973-12-7 5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one 
• 1420045-10-8 C₅₆H₅₀O₁₄ 

Downstream Products

• 700364-44-9 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 3,4,5-trihydroxybenzoate 

Relevant articles and documents

A novel semisynthetic flavonoid 7-O-galloyltaxifolin upregulates heme oxygenase-1 in RAW264.7 cells via MAPK/Nrf2 pathway

Quercetin and gallic acid are natural activators of the transcription factor Nrf2, which regulates the expression of many cytoprotective enzymes including heme oxygenase-1 (HO-1). We developed procedures for the synthesis of monogalloyl esters of quercetin and taxifolin (dihydroquercetin), namely, 3-O-galloylquercetin and 7-O-galloyltaxifolin, and examined their effect on the Nrf2 pathway in RAW264.7 cells. Unlike quercetin and free gallic acid, 3-O-galloylquercetin and natural quercetin derivatives isoquercitrin (quercetin-3-O-β-d-glucoside) and taxifolin had no effect on the expression of HO-1. In contrast, 7-O-galloyltaxifolin increased both mRNA and protein levels of HO-1 at concentrations of 25 μM and above. The induction of HO-1 by 7-O-galloyltaxifolin was primarily associated with the production of reactive oxygen species and phosphorylation of mitogen-activated protein kinases (MAPKs), including p38 MAPKs and ERKs, followed by nuclear accumulation of Nrf2 and downregulation of Keap1, a negative regulator of Nrf2. We conclude that 7-O-galloyltaxifolin upregulates HO-1 via activation of the MAPK/Nrf2 signaling pathway.