40957-83-3

Usage

Uses

Used in Analytical Chemistry:
Glycitein is used as a reference standard in the determination of glycitein in hydrolyzed dry soya extracts using reversed-phase high-performance liquid chromatography (RP-HPLC). It also serves as a standard for the analysis of soy isoflavones and metabolites in urine, helping to bind to recombinant estrogen and progesterone receptors to determine the relative binding affinity (RBA) for the detection of potential endocrine disruptors.
Used in Pharmaceutical Industry:
Glycitein demonstrates anti-cancer activity, making it a potential candidate for the development of therapeutic agents against cancer. Additionally, it has been shown to reduce plasma cholesterol levels, which can contribute to the management of cardiovascular diseases.
Used in Postmenopausal Health:
Glycitein exhibits the ability to reduce postmenopausal bone loss, suggesting its potential use in the development of treatments for osteoporosis and related bone health issues in postmenopausal women.

Biochem/physiol Actions

Glycitein is a soybean (yellow cultivar) isoflavonoid; its natural glycosides are synergistic with genistein in inducing specific gene expression. Glycitein may be used to study anti-oxidation processes at the level of gene transcription where it increases the binding of transcription factors [nuclear factor-E2-related factor 2 (Nrf2) and c-Jun] to the antioxidant response element (ARE) on HO-1 and NQO1 promoters. Glycitein may be used in combination with other isoflavonoids such as genistein and daidzein to study apoptosis.

InChI:InChI=1/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

Upstream product

• 17817-31-1 6,7,4'-trihydroxyisoflavone 
• 79744-58-4 1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4'-hydroxyphenyl)ethanone 
• 68-12-2 N,N-dimethyl-formamide 
• 6100-60-3 4-methoxybenzene-1,3-diol 
• 19009-24-6 3-hydroxy-4-methoxyphenyl formate 
• 124-63-0 methanesulfonyl chloride 
• 1237605-01-4 glycitein 4'-O-β-D-glucoside 
• 7298-16-0 4-methoxy-6-chloroacetyl-1,3-benzenediol 
• 269409-70-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 
• 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 
• 621-59-0 isovanillin 
• 40246-10-4 glycitin 
• 58115-20-1 1-(2,4-Dihydroxy-5-methoxyphenyl)-2-(4-hydroxyphenyl)-3,3-dimethoxy-1-propanone 

Downstream Products

• 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 
• 918158-53-9 4'-O-hexanoylglycitein 
• 944719-70-4 C₁₆H₁₀⁽²⁾H₂O₅ 
• 918158-56-2 methyl (4'-O-hexanoylglycitein-7-yl β-D-2'',3'',4''-triacetylglucopyranosid)uronate 
• 40246-10-4 glycitin 
• 936257-09-9 [6-Methoxy-3-(4-methoxycarbonylmethoxy-phenyl)-4-oxo-4H-chromen-7-yloxy]-acetic Acid Methyl Ester 
• 936257-10-2 6-{6-methoxy-3-[4-(5-methoxycarbonyl-pentyloxy)phenyl]-4-oxo-4H-chromen-7-yloxy}hexanoic acid methyl ester 
• 1237605-01-4 glycitein 4'-O-β-D-glucoside 
• 94105-91-6 4',7-dihydroxy-6-methoxyisoflavane 
• 17817-31-1 6,7,4'-trihydroxyisoflavone 

Relevant academic research and scientific papers

Hydrolysis of isoflavone glycosides by a thermostable β-glucosidase from pyrococcus furiosus

The recombinant β-glucosidase from the hyperthermophilic archaeon Pyrococcus furiosus was purified with a specific activity of 330 U/mg for genistin by His-trap chromatography. The specific activity of the purified enzyme followed the order genistin > daidzin > glycitin> malonyl glycitin > malonyl daidzin > malonyl genistin. The hydrolytic activity for genistin was highest at pH 6.0 and 95 °C with a half-life of 59 h, a K m of 0.5 mM, and a kcat of 6050 1/s. The enzyme completely hydrolyzed 1.0 mM genistin, daidzin, and glycitin within 100, 140, and 180 min, respectively. The soybean flour extract at 7.5% (w/v) contained 1.0 mM genistin, 0.9 mM daidzin, and 0.3 mM glycitin. Genistin, daidzin, and glycitin in the soybean flour extract were completely hydrolyzed after 60, 75, and 120 min, respectively. Of the reported β-glucosidases, P. furiosus β -glucosidase exhibited the highest thermostability, kcat, k cat/Km, yield, and productivity for hydrolyzing genistin. These results suggest that this enzyme may be useful for the industrial hydrolysis of isoflavone glycosides.

A new isoflavone glycoside from the stem bark of Sophora japonica

A new isoflavone glycoside, 6-methoxy-7-hydroxy-4′-O-β-d- glucosyl isoflavone, glycitein-4′-O-β-d-glucoside (10), along with nine known flavonoids, were isolated from the stem bark of Sophora japonica. The structures of these compounds were determined by analysis of spectroscopic data (1D -, 2D - NMR and HRMS). The inhibitory effects of all the isolated compounds on aldose reductase were evaluated in vitro. Among these compounds, daidzein (1), puerol A (4), and paratensein-7-O-glucoside (9) exhibited potent inhibitory effects, with IC50 values of 3.2, 6.4, and 1.9 μM, respectively.

A simple synthesis of 7,4′-dihydroxy-6-methoxyisoflavone, glycitein, the third soybean isoflavone

4-Methoxyresorcinol (3) was synthesized as the precursor for glycitein (6) synthesis by the oxidation of 3-hydroxy-4-methoxybenzaldehyde (1) to the aryl formate with H2O2 and a catalytic amount of SeO2. Glycitein (6) was synthesized by cyclization of 2,4,4′-trihydroxy-5-methoxydeoxybenzoin (5) with N,N-dimethylformamide, boron trifluoride diethyl ether, and methanesulfonyl chloride in a microwave oven.

Invention relates to a soybean in the process of synthesis method

The present invention relates to organic chemical and technical field of drug synthesis, relates to a soybean flavins and its analogue synthetic method, the soybean flavins that 6 - methoxy - 4', 7 - dihydroxy isoflavone. The invention push-type apparatus shown synthetic route, to synthesize soybean flavins that 6 - methoxy - 4', 7 - dihydroxy isoflavone and its analogs, synthetic route of the present invention high yield, the operation is simple, mild condition, suitable for large-scale preparation.

Synthesis of various kinds of isoflavones, isoflavanes, and biphenyl- ketones and their 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities

Forty-eight kinds of isoflavones (8), thirty-one isoflavanes (9), and forty-seven biphenyl-ketones (10, 10') were synthesized from eleven kinds of substituted phenols (11) and six phenylacetic acids (12). Among them, seventy-five compounds are new. The radical scavenging activities of these compounds were evaluated using 1,1- diphenyl-2-picrylhydrazyl (DPPH) at pH 6.0. We found that thirty-nine out of forty-three compounds having a catechol moiety on either the A- or the B-ring exhibited a high activity (ED50=12-54 μM) similar to that of catechin. In these cases, the remaining part of their structure seemed to have little effect on their activity. Many 6- or 8-hydroxyisoflavanes (9E-I) and their biphenyl-ketone derivatives (10E-H) also showed a high activity (ED50=50=26-32 μM). This study suggests that natural isoflavones have the possibilities of exhibiting antioxidant activities through the hydroxylation at the C6-, C8-, or C3'-position or the formation of the isoflavanes (9) and/or the biphenyl-ketone derivatives (10') by metabolism or biotransformation.

Anti-inflammatory mechanisms of isoflavone metabolites in lipopolysaccharide-stimulated microglial cells

The microglial activation plays an important role in neurodegenerative diseases by producing several proinflammatory cytokines and nitric oxide (NO). We found that three types of isoflavones and their metabolites that are transformed by the human intestin

Isoflavan and isoflavene compounds and their use as angiogenesis inhibitors

The present invention is directed to the use of a group of isoflavan and isoflav-3-ene compounds having the formula wherein R1 and R2 independently have the meaning of a hydroxy group, or a group that decreases the metabolism or increases the bioavailability of the compound, and the dotted line means an optional double bond, for the treatment of pathological conditions associated with or dependent on enhanced or abnormal angiogenesis in a mammal. The invention also concerns a group of novel isoflavan and isoflav-3-ene compounds.

METHOD FOR PURIFYING AND SEPARATING SOY ISOFLAVONES

A method for purifying isoflavones glycosides of genistin and daidzin from impurities present in a soy isoflavones concentrate. The method includes digesting a soy isoflavones concentrate with an acidic solution and separating insoluble solids from the acidic solution, wherein the solids are enriched in genistin and comprise glycosides of genistin and daidzin.

SYNTHESIS OF 13C-LABELLED ESTROGEN ANALOGUES

There is provided a method of producing novel 13C-labelled estrogen analogues. The method preferably proceeds via an intermediate A or B or which is a mixture of (A) or (B): wherein a13C atom is located at one or more of positions 1, 2, 3 or 4 and wherein R is an optionally substituted alkane, alkene, alkyne or aryl group. Preferably R is -CH2Ph. An alternative preferred intermediate compound is 13C-resorcinol.

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.