6743-92-6

Basic information

• Product Name: 3'-O-Methylquercetin 3-galactoside
• Synonyms: 2-(4-Hydroxy-3-methoxyphenyl)-3-(β-D-galactopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one;3-(β-D-Galactopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one;3'-O-Methylquercetin 3-galactoside;Cacticin;Isorhamnetin 3-galactoside;Isorhamnetin 3-O-galactoside;Isorhamnetol 3-O-galactoside;5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS NO: 6743-92-6
• Molecular Formula: C₂₂H₂₂O₁₂
• Molecular Weight: 478.41
• Mol File: 6743-92-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 267-269℃
• Boiling Point: 834.36oC at 760 mmHg
• Flash Point: 291.284oC
• Appearance: /
• Density: 1.75±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.75
• PKA: 6.17±0.40(Predicted)
• CAS DataBase Reference: 3'-O-Methylquercetin 3-galactoside(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-O-Methylquercetin 3-galactoside(6743-92-6)
• EPA Substance Registry System: 3'-O-Methylquercetin 3-galactoside(6743-92-6)

Safety Data

• Hazardous Substances Data: 6743-92-6(Hazardous Substances Data)

Usage

Description

3'-O-Methylquercetin 3-galactoside is a flavonoid compound, a glycoside derivative of quercetin, characterized by the attachment of a galactose sugar molecule to the quercetin structure. This natural pigment is found in various fruits and vegetables and has been recognized for its potential health benefits, such as antioxidant and anti-inflammatory properties. It is also under investigation for its possible role in cancer prevention and treatment, making it a biologically active compound with promising therapeutic applications.

Uses

Used in Pharmaceutical Industry:
3'-O-Methylquercetin 3-galactoside is used as a therapeutic agent for its potential health benefits, particularly due to its antioxidant and anti-inflammatory properties. It is being studied for its role in cancer prevention and treatment, indicating its potential as a chemopreventive or chemotherapeutic agent.
Used in Nutraceutical Industry:
In the nutraceutical sector, 3'-O-Methylquercetin 3-galactoside is utilized as a dietary supplement ingredient, capitalizing on its antioxidant properties to support overall health and well-being.
Used in Cosmetic Industry:
3'-O-Methylquercetin 3-galactoside is employed as an active ingredient in cosmetic products for its potential skin health benefits, including anti-inflammatory and antioxidant effects that may contribute to skin protection and rejuvenation.
Used in Food and Beverage Industry:
3'-O-Methylquercetin 3-galactoside is also used in the food and beverage industry as a natural colorant and for its potential health-promoting properties, enhancing the nutritional value of products while providing a vibrant color.

InChI:InChI=1/C22H22O12/c1-31-12-4-8(2-3-10(12)25)20-21(17(28)15-11(26)5-9(24)6-13(15)32-20)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3/t14-,16+,18+,19-,22?/m1/s1

Upstream product

• 117-39-5 quercetol 
• 2956-16-3 uridine 5'-diphospho-D-galactose 
• 480-19-3 isorhamnetin 
• 78386-02-4 7-(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)- 3,5-dihydroxy-4H-chromen-4-one 
• 17429-69-5 isorhamnetin 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside 
• 133-89-1 UDP-glucose 
• 482-35-9 quercetin-3-O-glucoside 
• 78386-01-3 2-(3-acetoxy-4-(benzyloxy) phenyl)-7-(benzyloxy)-4-oxo-4H-chromene-3,5-diyl diacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 1346137-81-2 3,5,7,4'-tetrahydroxy-3'-methoxyflavone-3-O-[6''-O-(3'''-hydroxy-3'''-methylglutaroyl)]-β-D-galactopyranoside 
• 107603-09-8 3-<6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl>oxy-5-hydroxy-7-<β-L-mannopyranosyl>oxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzo-pyran-4-one 
• 604-80-8 narcissin 
• 119945-82-3 isorhamnetin 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside 
• 103839-19-6 3,5,7,4′-tetrahydroxy-8,3′-dimethoxyflavone-3-O-β-D-glucopyranoside 

Downstream Products

• 480-19-3 isorhamnetin 
• 2280-44-6 D-Glucose 
• 50-99-7 D-glucose 
• 10257-28-0 D-Galactose 
• 1244-78-6 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone 

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.

Effects of Functional Groups and Sugar Composition of Quercetin Derivatives on Their Radical Scavenging Properties

Quercetin derivatives are widespread in the plant kingdom and exhibit various biological actions. The aim of this study was to investigate the structure-activity relationships of quercetin derivatives, with a focus on the influence of functional groups and sugar composition on their antioxidant capacity. A series of quercetin derivatives were therefore prepared and assessed for their DPPH radical scavenging properties. Isoquercetin O-gallates were more potent radical scavengers than quercetin. The systematic analysis highlights the importance of the distribution of hydroxy substituents in isoquercetin O-gallates to their potency.

Phenolic constituents of the inflorescences of Sorbus torminalis (L.) Crantz

Torminaloside, a new acylated flavonol glycoside (3,5,7,4′- tetrahydroxy-3′-methoxyflavone-3-O-[6″-O-(3?-hydroxy- 3?-methylglutaroyl)]-β-d-galactopyranoside, 6), together with five further methoxylated flavones 1-5, hyperoside (7), isoquercitrin (8), chlorogenic acid (9) and neochlorogenic acid (10), were isolated for the first time from Sorbus torminalis (L.) Crantz. The structures of the isolates were elucidated by extensive spectroscopic studies, including UV, IR, 1D- and 2D-NMR, LSI-MS and HR-LSI-MS experiments. In addition to torminaloside, three further flavonoids: 5,7,4′-trihydroxy-3′-methoxyflavone-7-O-β-d- glucopyranoside (1), 3,5,7,4′-tetrahydroxy-8,3′-dimethoxyflavone-3- O-β-d-glucopyranoside (2), and 3,5,7,4′-tetrahydroxy-3′- methoxyflavone-3-O-β-d-galactopyranoside (4) were found for the first time in the genus Sorbus.