Glycitein Chemical Properties

Melting point:

>300°C

Boiling point:

547.4±50.0 °C(Predicted)

Density 

1.420±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Aqueous Base (Slightly), DMSO (Slightly)

pka

7.03±0.20(Predicted)

form 

Solid

color 

Light Brown

biological source

synthetic (organic)

InChI

InChI=1S/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

InChIKey

DXYUAIFZCFRPTH-UHFFFAOYSA-N

SMILES

C1OC2=CC(O)=C(OC)C=C2C(=O)C=1C1=CC=C(O)C=C1

LogP

2.570 (est)

CAS DataBase Reference

40957-83-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29329990

MSDS

• Language:English Provider:SigmaAldrich

Glycitein Usage And Synthesis

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

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).

Uses

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.

Uses

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.

Synthesis

Under nitrogen protection, boron trifluoride ethyl ether complex (1.6 mL, 13.13 mmol) was slowly added to an anhydrous N,N-dimethylformamide (10 mL) solution of deoxybenzene coupling (0.6 g, 2.19 mmol). After 15 min of reaction, anhydrous N,N-dimethylformamide (2 mL) solution of methanesulfonyl chloride (0.84 mL, 10.95 mmol) was added dropwise. The reaction mixture was heated and stirred in an oil bath at 70°C for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice-cooled saturated aqueous sodium acetate solution (50 mL). The precipitated solid was collected by filtration and recrystallized from 70% ethanol to afford 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-benzopyran-4-one as a yellow solid (0.53 g, 85% yield) with a melting point of 336-338°C. The product structure was determined by 1H NMR. The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6) and mass spectrometry (EI, 70 eV): 1H NMR δ 10.63 (br s, 1H, 7-OH), 9.54 (br s, 1H, 4'-OH), 8.27 (s, 1H, H-2), 7.41 (s, 1H, H-5), 7.37 (d, J = 8.7 Hz. 2H, H-2', 6'), 6.92 (s, 1H, H-8), 6.79 (d, J = 8.7 Hz, 2H, H-3', 5'), 3.86 (s, 3H, OCH3); mass spectra m/z 284 (M+, 24%), 283 (100), 268 (15), 255 (20), 212 (41), 171 (15).

References

[1] Patent: US2007/203227, 2007, A1. Location in patent: Page/Page column 3

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