40957-83-3

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.

Pale Orange Solid

The compund shows an anti-cancer activity, plasma cholesterol reduction, reduction in postmenopausal bone loss

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.

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.

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).

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