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

Description

Glycitin, an isoflavonoid found in the flowers of Pueraria thunbergiana, is a glycosyloxyisoflavone with a methoxy group at position 6, a hydroxy group at position 4', and a beta-D-glucopyranosyloxy group at position 7. It can be modified into the metabolite glycitein, which possesses anti-inflammatory properties. Glycitin is a white solid and has been identified as a derivative of Glycitein and an inhibitor.

Uses

Used in Pharmaceutical Industry:
Glycitin is used as an inhibitor for its potential therapeutic applications. As a metabolite of isoflavone derivatives, it can be utilized in the development of new drugs targeting various health conditions.
Used in Nutraceutical Industry:
Glycitin, with its anti-inflammatory properties through its metabolite glycitein, can be used as a key ingredient in the development of nutraceutical products aimed at promoting health and well-being.
Used in Cosmetic Industry:
Due to its anti-inflammatory properties, Glycitin can be used as an active ingredient in cosmetic products, particularly those targeting skin health and inflammation reduction.
Used in Research and Development:
Glycitin's unique chemical structure and properties make it a valuable compound for research and development in various scientific fields, including pharmacology, biochemistry, and biotechnology.

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

• 1105697-69-5 4'-O-hexanoylglycitein-7-yl 2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranoside 
• 133-89-1 UDP-glucose 
• 40957-83-3 glycitein 
• 50-99-7 D-glucose 
• 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 
• 58115-19-8 2-(4-Benzyloxy-phenyl)-1-(2,4-bis-benzyloxy-5-methoxy-phenyl)-3,3-dimethoxy-propan-1-one 

Downstream Products

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

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.