35212-22-7

Ipriflavone(35212-22-7), a derivative of isoflavone, is a calcium metabolism regulator useful in the treatment of primary and secondary osteoporosis, as well as disorders of osteogenesis. It appears to be without significant side-effects.

white powder

Chinoin (Japan)

anabolic

ChEBI: A member of the class of isoflavones that is isoflavone in which the hydrogen at position 7 is replaced by an isopropoxy group. A synthetic isoflavone, it was formerly used for the treatment of osteoporosis, although a randomised controlled study failed to show any benefit. It is still used to prevent osteoporosis in post-menopausal women.

Osten

Ipriflavone(35212-22-7) is used clinically to treat osteoporosis. Bodybuilders also use ipriflavone, but enough experimental data supports this purpose. It has been shown to have anti-inflammatory and antioxidant activity. It helps to reduce bone loss, increase bone density, and reduce the risk of developing osteoporosis. It has also been found to help reduce neuroinflammation . In addition, it has been found to help reduce the risk of certain types of cancer, improve cognitive function and reduce the risk of depression.

Ipriflavone should be taken under medical supervision only. It can produce side effects such as stomach pain, diarrhoea, dizziness, etc. It may have a sudden increase in the WBC count if administered for six months or more. When the treatment with Ipriflavone is on, it is suggested that the WBC count should be monitored. 

General procedure for the synthesis of epoxyflavone from 7-hydroxy-3-phenyl-4H-benzopyran-4-one and 2-bromopropane: To a 30 ml DMF solution of 2.50 g of 7-hydroxy-3-phenyl-4H-benzopyran-4-one (10.5 mmol) was added 1.80 g of anhydrous K2CO3 (13.0 mmol) and 3.0 ml of 2-bromopropane ( 32.0 mmol). The reaction mixture was stirred at 80 °C for 4 h. After completion of the reaction, the mixture was poured into ice water. The precipitate was collected by filtration and washed with a small amount of water and dried to give the crude product. The crude product was purified by Sephadex LH-20 column chromatography (eluent: chloroform:methanol = 7:3), and the fraction containing the target product was collected, concentrated, and recrystallized from acetone to give 1.05 g of epsilon-flavonoid crystals with a yield of 42% (w/w) and a melting point of 110-111 °C. The product structure was determined by 1H NMR. The structure of the product was confirmed by 1H NMR, 13C NMR and mass spectrometry (MS).1H NMR (DMSO-d6) δ: 1.33 (-CH3), 1.34 (-CH3), 4.86 (m, 1H, >CH2-), 7.05 (dd, 1H, J = 8.86, 2.20 Hz, 6-H), 7.16 (d, 1H, J = 2.50 Hz, 8-H), 7.38 (t, 1H, J = 6.78 Hz, 4'-H), 7.44 (t, 2H, J = 7.76, 1.6 Hz, 3',5'-H), 7.59 (d, 2H, J = 8.09, 1.6 Hz, 2',6'-H), 8.22 (d, 1H, J = 8.86 Hz, 5-H), 8.46 (s, 1H 128.1 (C-3',5'), 128.9 (C-2',6'), 132.0 (C-4'), 154.0 (C-2), 157.5 (C-9), 162.0 (C-7), 174.1 (C-4). , 279.5 (M-H)-. Elemental analysis (C18H16O3) calculated values: C, 77.12; H, 5.75. measured values: C, 76.50; H, 5.69.

Ipriflavone inhibits the proliferation and DNA synthesis of MDA-231 cells and blocks the ligand-induced phosphorylation of Tyr(845) of the EGFR. Ipriflavone does not promote apoptosis of MDA-231 cells. Ipriflavone also promotes the deposition of calcium and the formation of mineralized nodules by newborn rat calvarial osteoblast-like cells as well as the activity of alkaline phosphatase.

Ipriflavone ameliorated the host inflammatory response associated with activation of NLRP3 inflammasomes at the implantation site, which was characterised by inflammatory cell infiltration and reduced levels of the pro-inflammatory cytokine interleukin-1β. Daily oral administration of ipriflavone at 12 mg/mouse significantly inhibits the development of new osteolytic bone metastases and the progression of established osteolytic lesions, prolonging the life of tumor-bearing mice. Ipriflavone reduces the number of osteoclasts at the bone-cancer interface with no severe adverse effects on the host. 1-month treatment with ipriflavone increases bone density and improves the biomechanical properties of adult rat male bones without altering mineral composition.

Store at -20°C

[1] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # 5, p. 497 - 504
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 18, p. 4069 - 4081
[3] Patent: WO2004/2470, 2004, A1. Location in patent: Page/Page column 22-23
[4] Patent: US3949085, 1976, A