| Identification | More | [Name]
Ipriflavone | [CAS]
35212-22-7 | [Synonyms]
7-(1-methylethoxy)-3-phenyl-4h-1-benzopyron-4-one
7-ISOPROPOXY-3-PHENYL-4H-1-BENZOPYRAN-4-ONE
7-ISOPROPOXYISOFLAVONE
7-ISOPROPYLOXYISOFLAVONE
7-Isoproxyisoflavone
IPRIFLAVONE
osteofix
YAMBOLAP
7-(1-methylethoxy)-3-phenyl-4h-1-benzopyran-4-on
7-(1-methylethoxy)-3-phenyl-4h-1-benzopyran-4-one
fl113
osten
tc80
Iprflavone
IPRIFLAVONE(P)
Ipriflavon
7-ISOPROPOXY-3-PHENYL-4H-1-BENZOPYRAN-4-ONE 97%
7-ISOPROPOXYISOFLAVONE JP
IOPAMIDOLUSP2960166-93-0
IPRIFLAVONE (7-ISOPROPOXYISOFLAVONE) | [EINECS(EC#)]
201-641-0 | [Molecular Formula]
C18H16O3 | [MDL Number]
MFCD00221719 | [Molecular Weight]
280.32 | [MOL File]
35212-22-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white powder | [Melting point ]
116-120 °C(lit.)
| [Boiling point ]
363.04°C (rough estimate) | [density ]
1.2170 (rough estimate) | [refractive index ]
1.4700 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMF:20.0(Max Conc. mg/mL);71.35(Max Conc. mM)
DMF:PBS (pH 7.2) (1:4):0.2(Max Conc. mg/mL);0.71(Max Conc. mM)
DMSO:33.11(Max Conc. mg/mL);118.11(Max Conc. mM)
Ethanol:1.5(Max Conc. mg/mL);5.35(Max Conc. mM) | [form ]
powder to crystal | [color ]
White to Almost white | [Merck ]
5074 | [InChI]
InChI=1S/C18H16O3/c1-12(2)21-14-8-9-15-17(10-14)20-11-16(18(15)19)13-6-4-3-5-7-13/h3-12H,1-2H3 | [InChIKey]
SFBODOKJTYAUCM-UHFFFAOYSA-N | [SMILES]
C1OC2=CC(OC(C)C)=CC=C2C(=O)C=1C1=CC=CC=C1 | [LogP]
4.245 (est) | [CAS DataBase Reference]
35212-22-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S27:Take off immediately all contaminated clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
2
| [RTECS ]
DJ3100500
| [HS Code ]
29329990 |
| Hazard Information | Back Directory | [Description]
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.
| [Chemical Properties]
white powder | [Originator]
Chinoin (Japan) | [Uses]
anabolic | [Definition]
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. | [Brand name]
Osten | [benefits]
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.
| [General Description]
7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one (Ipriflavone,35212-22-7), a synthetic flavonoid, is reported to stimulate the activity of osteoblasts. It is reported to promote the deposition of calcium and the formation of mineralized nodules by newborn rat calvarial osteoblast-like (ROB) cells as well as the activity of alkaline phosphatase. Ipriflavone, an isoflavone derivative, is a new drug used to decrease bone loss in osteoporosis.
| [Side effects]
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. | [Synthesis]
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. | [in vitro]
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. | [in vivo]
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. | [storage]
Store at -20°C | [References]
[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 |
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