20229-56-5

Basic information

• Product Name: SPIRAEOSIDE
• Synonyms: 2-(4-(beta-d-glucopyranosyloxy)-3-hydroxyphenyl)-3,5,7-trihydroxy-4h-1-benzo;4h-1-benzopyran-4-one,2-(4-(beta-d-glucopyranosyloxy)-3-hydroxyphenyl)-3,5,7-t;spiraein(acacia);spiraeosid;2-[4-(beta-D-glucopyranosyloxy)-3-hydroxyphenyl]-3,5,7-trihydroxy-4H-1-benzopyran-4-one;SPIRAEOSIDE(RG);QUERCETIN4OBETAGLUCOSIDE;QUERCETIN4GLUCOSIDE
• CAS NO: 20229-56-5
• Molecular Formula: C₂₁H₂₀O₁₂
• Molecular Weight: 464.38
• EINECS: 243-614-6
• Product Categories: Miscellaneous Natural Products
• Mol File: 20229-56-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 209-211°C
• Boiling Point: 835.6 °C at 760 mmHg
• Flash Point: 294.6 °C
• Appearance: /
• Density: 1.809g/cm³
• Storage Temp.: ?20°C
• PKA: 6.31±0.40(Predicted)
• CAS DataBase Reference: SPIRAEOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: SPIRAEOSIDE(20229-56-5)
• EPA Substance Registry System: SPIRAEOSIDE(20229-56-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 20229-56-5(Hazardous Substances Data)

Usage

Uses

Quercetin 4''-Glucoside was found to be a pigment flavonoid in Montmorency cherries. Quercetin 4''-Glucoside has been seen to increase the antioxidant capacity of blood plasma.

Upstream product

• 133-89-1 UDP-glucose 
• 117-39-5 quercetol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 498548-14-4 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-tribenzyloxy-4H-chromen-4-one 
• 498548-15-5 3,7-bis(benzyloxy)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-chromen-4-one 
• 357194-03-7 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one 
• 1313191-85-3 2-(4-O-β-D-glucopyranosyloxy-3-benzyloxyphenyl)-3,5,7-tribenzyloxy-4H-chromen-4-one 
• 1313191-84-2 2-(4-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-3-benzyloxyphenyl)-3,5,7-tribenzyloxy-4H-chromen-4-one 
• 1313191-83-1 C₄₃H₄₀O₁₆ 

Downstream Products

• 117-39-5 quercetol 
• 2280-44-6 D-Glucose 

Relevant articles and documents

Quercetin-4'-glucoside is more potent than quercetin-3-glucoside in protection of rat intestinal mucosa homogenates against iron ion-induced lipid peroxidation.

Quercetin is a typical antioxidative flavonoid found in vegetables, which is more commonly present as its glucosides, quercetin-3-glucoside (Q3G) and quercetin-4'-glucoside (Q4'G). The main aim of this study was to estimate the antioxidant activity of Q3G and Q4'G on iron ion-driven lipid peroxidation of the gastrointestinal mucosa. Q4'G markedly suppressed the lipid peroxidation when rat gastrointestinal mucosa homogenates were incubated with Fe(NO3)3 and ascorbic acid. Its effectiveness was greater as compared to that of Q3G and comparable to that of quercetin aglycone. Furthermore, Q4'G yielded higher amounts of quercetin aglycone than Q3G on incubation with the homogenates. However, Q4'G showed a lower chelating activity in comparison to Q3G. These results indicate that Q4'G, even though it has a low chelating activity, because of its efficient conversion to antioxidative aglycone on exposure to the mucosa, can act as a powerful antioxidant on iron ion driven lipid peroxidation in the intestinal mucosa. Thus, vegetables rich in Q4'G, such as onion, are likely to serve as favorable antioxidant sources for suppressing iron-induced oxidative stress in the intestinal tract.

A glycosynthase catalyst for the synthesis of flavonoid glycosides

Mutant exposed! The synthetic utility of glycosynthase mutant enzymes has been expanded to allow the use of lipophilic acceptors, such as flavonoids, at rates comparable with those of natural glycosyltransferases. Sequential biocatalysis allows access to both di- and monosaccharide-modifled products as well as natural product glycoflavonoids. (Figure Presented).

Cloning and functional characterisation of two regioselective flavonoid glucosyltransferases from Beta vulgaris

Two full-length cDNAs encoding flavonoid-specific glucosyltransferases, UGT73A4 and UGT71F1, were isolated from a cDNA library of Beta vulgaris (Amaranthaceae) cell suspension cultures. They displayed high identity to position-specific betanidin and flavonoid glucosyltransferases from Dorotheanthus bellidiformis (Aizoaceae) and to enzymes with similar substrate specificities from various plant families. The open reading frame of the sequences encode proteins of 476 (UGT73A4) and 492 (UGT71F1) amino acids with calculated molecular masses of 54.07 kDa and 54.39 kDa, and isoelectric points of 5.8 and 5.6, respectively. Both enzymes were functionally expressed in Escherichia coli as His- and GST-tagged proteins, respectively. They exhibited a broad substrate specificity, but a distinct regioselectivity, glucosylating a variety of flavonols, flavones, flavanones, and coumarins. UGT73A4 showed a preference for the 4′- and 7-OH position in the flavonoids, whereas UGT71F1 preferentially glucosylated the 3- or the 7-OH position. Glucosylation of betanidin, the aglycone of the major betacyanin, betanin, in B. vulgaris was also observed to a low extent by both enzymes. Several O-glycosylated vitexin derivatives isolated from leaves of young B. vulgaris plants and rutin obtained from B. vulgaris tissue culture are discussed as potential endogenous products of UGT73A4 and UGT71F1. The results are analyzed with regard to evolution and specificity of plant natural product glucosyltransferases.