Ipriflavone Chemical Properties

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 

14,5074

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36/37/39-27-26

WGK Germany 

2

RTECS 

DJ3100500

HS Code 

29329990

MSDS

• Language:English Provider:Ipriflavone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Ipriflavone Usage And Synthesis

Description

Ipriflavone, 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

7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one (Ipriflavone) has been used as a model drug in a study to functionalize the mesoporous bioactive glasses (MBG). Study suggested that since ipriflavone is a hydrophobic anti-osteoporotic drug, it easily attaches to the surface of MBG and results in long-term drug delivery.

Uses

anabolic

Definition

ChEBI: Ipriflavone is 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. It has a role as a bone density conservation agent. It is a member of isoflavones and an aromatic ether.

brand name

Osten

benefits

Ipriflavone 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), 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.

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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