40957-83-3

Basic information

• Product Name: Glycitein
• Synonyms: GLYCETEIN;GLYCITEIN;4',7-DIHYDROXY-6-METHOXYISOFLAVONE;4,7-DIHYDROXY-6-METHOXYISOFLAVONE;7,4'-DIHYDROXY-6-METHOXYISOFLAVONE; Glicetein;7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one;4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-
• CAS NO: 40957-83-3
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• Product Categories: Iso-Flavones;The group of Daidzin;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;inhibitor
• Mol File: 40957-83-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: >300°C
• Boiling Point: 547.4 °C at 760 mmHg
• Flash Point: 210 °C
• Appearance: Pale orange solid
• Density: 1.42 g/cm³
• Vapor Pressure: 1.36E-12mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: −20°C
• Solubility: Aqueous Base (Slightly), DMSO (Slightly)
• PKA: 7.03±0.20(Predicted)
• CAS DataBase Reference: Glycitein(CAS DataBase Reference)
• NIST Chemistry Reference: Glycitein(40957-83-3)
• EPA Substance Registry System: Glycitein(40957-83-3)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 40957-83-3(Hazardous Substances Data)

Usage

Description

Glycitein is an O-methylated isoflavone that comprises 5-10% of the total isoflavones in soy food products. This phytoestrogen is reported to have weak estrogenic activity, displacing estradiol binding at the estrogen receptor in vitro with an IC50 value of 3.94 μM. It suppresses the proliferation of osteoblasts and promotes differentiation from its progenitor. It has also been used to attenuate proliferation (10 μM) of aortic smooth muscle cells related to atherosclerotic vascular change in stroke-prone hypertensive rats and to protect against beta amyloid (Aβ)-induced toxicity and oxidative stress (100 μg/ml) in C. elegans expressing human Aβ.

Chemical Properties

Pale Orange Solid

Uses

Different sources of media describe the Uses of 40957-83-3 differently. You can refer to the following data:
1. Glycitein may be used as a reference standard in the determination of glycitein in hydrolyzed dry soya extracts using reversed-phase high-performance liquid chromatography (RP-HPLC).
2. Glycitein has been used as standard for the analysis of soy isoflavones and metabolites in urine. It has also been used to bind to recombinant estrogen and progesterone receptors to know the relative binding affinity (RBA) for detection of potential endocrine disruptors.
3. The compund shows an anti-cancer activity, plasma cholesterol reduction, reduction in postmenopausal bone loss

Definition

ChEBI: A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis.

General Description

Glycitein is an isoflavone found in soy food products.

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

• 67-56-1 methanol 
• 486-66-8 daidzein 
• 124-63-0 methanesulfonyl chloride 
• 79744-58-4 1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4'-hydroxyphenyl)ethanone 
• 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 
• 1237605-01-4 glycitein 4'-O-β-D-glucoside 
• 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 
• 19009-24-6 3-hydroxy-4-methoxyphenyl formate 
• 6100-60-3 4-methoxybenzene-1,3-diol 
• 621-59-0 isovanillin 
• 40246-10-4 glycitin 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 17817-31-1 6,7,4'-trihydroxyisoflavone 
• 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 
• 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 
• 40246-10-4 glycitin 
• 1237605-01-4 glycitein 4'-O-β-D-glucoside 
• 94105-91-6 4',7-dihydroxy-6-methoxyisoflavane 
• 918158-56-2 methyl (4'-O-hexanoylglycitein-7-yl β-D-2'',3'',4''-triacetylglucopyranosid)uronate 
• 944719-70-4 C₁₆H₁₀⁽²⁾H₂O₅ 
• 918158-53-9 4'-O-hexanoylglycitein 

Relevant articles and documents

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 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.

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.