22255-13-6

Basic information

• Product Name: guajavarin
• Synonyms: guajavarin;2-(3,4-Dihydroxyphenyl)-3-(α-L-arabinopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one;3-[(α-L-Arabinopyranosyl)oxy]-3',4',5,7-tetrahydroxyflavone;Foeniculin(glycoside);Guaijaverin;Quercetin 3-O-α-arabinoside;Quercetin 3-α-L-Arabinopyranoside;3-(alpha-L-Arabinopyranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
• CAS NO: 22255-13-6
• Molecular Formula: C₂₀H₁₈O₁₁
• Molecular Weight: 434.351
• Mol File: 22255-13-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 237-239 °C
• Boiling Point: 828.061 °C at 760 mmHg
• Flash Point: 296.325 °C
• Appearance: /
• Density: 1.86
• Storage Temp.: room temp
• Solubility: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• PKA: 6.17±0.40(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: guajavarin(CAS DataBase Reference)
• NIST Chemistry Reference: guajavarin(22255-13-6)
• EPA Substance Registry System: guajavarin(22255-13-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 22255-13-6(Hazardous Substances Data)

Usage

Uses

Quercetin 3-O-α-L-Arabinopyranoside is a derivative of Quercetin (Q509500), a flavonoid with anticancer activity. It is a mitochondrial ATPase and phosphodiesterase inhibitor. It Inhibits PI3-kinase activity and slightly inhibits PIP kinase activity. Quercetin has antiproliferative effects on cancer cell lines, reduces cancer cell growth via type II estrogen receptors, and arrests human leukemic T cells in late G1 phase of the cell cycle.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

quercetin 3-O-α-L-arabinopyranoside was shown to inhibit the activity of glucose-6-phosphatase.

Upstream product

• 117-39-5 quercetol 
• 21401-20-7 C₁₄H₂₂N₂O₁₆P₂ 
• 742062-22-2 Acetic acid (2S,3R,4S,5S)-4,5-diacetoxy-2-[2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-3-yl ester 
• 357194-03-7 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one 

Downstream Products

• 1244-78-6 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone 
• 10323-20-3 D-Arabinose 
• 117-39-5 quercetol 
• 87-72-9 L-(+)-arabinose 
• 94035-82-2 avicularin heptaacetate 

Relevant articles and documents

Highly Promiscuous Flavonoid 3- O-Glycosyltransferase from Scutellaria baicalensis

A highly regio-specific and donor-promiscuous 3-O-glycosyltransferase, Sb3GT1 (UGT78B4), was discovered from Scutellaria baicalensis. Sb3GT1 could accept five sugar donors (UDP-Glc/-Gal/-GlcNAc/-Xyl/-Ara) to catalyze 3-O-glycosylation of 17 flavonols, and the conversion rates could be >98%. Five new glycosides were obtained by scaled-up enzymatic catalysis. Molecular modeling and site-directed mutagenesis revealed that G15 and P187 were critical catalytic residues for the donor promiscuity. Sb3GT1 could be a promising catalyst to increase structural diversity of flavonoid 3-O-glycosides.