40246-10-4

Basic information

• Product Name: Glycitin
• Synonyms: Glycitin, froM GlycineMax (L.) Merr.;4H-1-Benzopyran-4-one, 7-(β-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-6-methoxy-;Glycitin, >99%;Glycitin, >=98%;Daidzin/Glycitin;4H-1-Benzopyran-4-one 7-(β-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-6-methoxy-Glycitein Glycitein 7-O-β-glucoside;GLYCITEIN 7-O-GLUCOSIDE;GLYCITIN
• CAS NO: 40246-10-4
• Molecular Formula: C₂₂H₂₂O₁₀
• Molecular Weight: 446.4
• Product Categories: inhibitor;Inhibitors;Miscellaneous Natural Products;The group of Daidzin;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Glucuronides;Heterocycles;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 40246-10-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 2100C
• Boiling Point: 751.1 °C at 760 mmHg
• Flash Point: 264.1 °C
• Appearance: White solid
• Density: 1.545
• Vapor Pressure: 1.07E-23mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: Store at -20
• Solubility: DMSO (Slightly, Sonicated), Methanol (Slightly, Heated)
• PKA: 9.62±0.30(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Glycitin(CAS DataBase Reference)
• NIST Chemistry Reference: Glycitin(40246-10-4)
• EPA Substance Registry System: Glycitin(40246-10-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 40246-10-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 40246-10-4 differently. You can refer to the following data:
1. A derivative of Glycitein. Inhibitor
2. A metabolite of isoflavone derivatives.
3. A metabolite of isoflavone derivatives. A derivative of Glycitein. Inhibitor.

Definition

ChEBI: A glycosyloxyisoflavone that is isoflavone substituted by a methoxy group at position 6, a hydroxy group at position 4' and a beta-D-glucopyranosyloxy group at position 7.

General Description

Glycitin is an isoflavonoid recently found in flowers of Pueraria thunbergianaI. Glycitin can be modified into the metabolite glycitein which has anti-inflammatory properties.

Biochem/physiol Actions

Glycitin is a soy isoflavone in the glucoside form. A rat model study demonstrated glycitin to be effective in preventing bone loss and reversing the unfavorable changes of lipid metabolism in this model.

InChI:InChI=1/C22H22O10/c1-29-15-6-12-14(30-9-13(18(12)25)10-2-4-11(24)5-3-10)7-16(15)31-22-21(28)20(27)19(26)17(8-23)32-22/h2-7,9,17,19-24,26-28H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1

Upstream product

• 40957-83-3 glycitein 
• 50-99-7 D-glucose 
• 133-89-1 UDP-glucose 
• 1105697-69-5 4'-O-hexanoylglycitein-7-yl 2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranoside 
• 58115-19-8 2-(4-Benzyloxy-phenyl)-1-(2,4-bis-benzyloxy-5-methoxy-phenyl)-3,3-dimethoxy-propan-1-one 
• 7298-22-8 2,4-Dibenzyloxy-5-methoxyacetophenone 
• 58115-20-1 1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone 
• 182284-73-7 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[3-(4-hydroxy-phenyl)-6-methoxy-4-oxo-4H-chromen-7-yloxy]-tetrahydro-pyran-3-yl ester 

Downstream Products

• 1237605-04-7 glycitein 7-O-β-maltoside 
• 1237605-05-8 glycitein 7-O-β-maltotrioside 
• 40957-83-3 glycitein 

Relevant articles and documents

Identification of a flavonoid 7-O-glucosyltransferase from Andrographis paniculata

Andrographis paniculata is an important traditional medicinal herb in which flavonoids are part of the primary specialized metabolites. A flavonoid glucosyltransferase with broad substrate spectrum (named ApUGT3) was successfully identified by screening homologous glycosyltransferase genes from A. paniculata. The enzyme displayed glycosylation activity toward multiple flavonoids in?vitro, and the major products were identified as 7-O-glucosides. Phylogenetic analysis revealed that ApUGT3 is the first reported glycosyltransferase from the Acanthaceae family that belongs to cluster I, suggesting that ApUGT3 is a new flavonoid glycosyltransferase of this subcluster. This enzyme is potentially useful as powerful glycosylation catalysts to modify flavonoid-like compounds and improve their biological activities. (Figure presented.).

An efficient method for the glycosylation of isoflavones

The isoflavone phytoestrogens are still of current interest for their positive and negative health benefits. However, there are still many unanswered questions regarding their absorption, metabolism and bioavailability. Studies in this area require access to samples of both the isoflavone 7-O-glucosides, the form found in plants and the 7-O-glucuronides, which are important mammaliam metabolites. A new efficient, high-yielding glycosylation procedure is described for isoflavones, which employs 2,2,2-trifluoro-N-(p-methoxyphenyl) acetamidates as the glycosyl donors. This methodology was used to prepare the 7-O-glycosides of the three main isoflavones, daidzein, genistein and glycitein. The isoflavones were protected with hexanoyl groups which improved their solubility in organic solvents and improved the efficiency of the reaction. The same methodology was then adapted for the synthesis of the analogous 7-O-glucuronides. The new synthesis will provide access to large quantities of these compounds for further biological studies. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis of 4′,7-dihydroxy-6-methoxyisoflavone 7-O-β-D-glucopyranoside (glycitin)

The aglycone glycitein (1) of the title glucoside glycitin (2) was prepared by oxidative rearrangement of the fully protected chalcone 4 by Tl(NO3)3 in MeOH into 5 followed by deprotection and ring closure. Its glucosylation with α-acetobromoglucose and subsequent saponification gave 2 as the main product. VCH Verlagsgesellschaft mbH, 1996.