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381551 Aldrich

7-Isopropoxy-3-phenyl-4H-1-benzopyran-4-one

97%

Synonym: Ipriflavone

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Properties

Related Categories Building Blocks, Chemical Synthesis, Heterocyclic Building Blocks, Pyrans
assay   97%
mp   116-120 °C(lit.)
Gene Information   rat ... Alpl(25586)

Description

Packaging

5 g in glass bottle

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.1 Ipriflavone, an isoflavone derivative, is a new drug used to decrease bone loss in osteoporosis.2

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Safety & Documentation

Safety Information

WGK Germany 
2
RTECS 
DJ3100500

Protocols & Articles

Peer-Reviewed Papers

References

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1. Ipriflavone down-regulates endothelin receptor levels during differentiation of rat calvarial osteoblast-like cells. Hagiwara H, Naruse M, Adachi C, et al. J. Biochem. 126(1), 168-73, (1999)

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2. Ipriflavone directly inhibits osteoclastic activity. Albanese CV, Cudd A, Argentino L, et al. Biochem. Biophys. Res. Commun. 199(2), 930-6, (1994)

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[Effect of ipriflavone on Wistar rats and their litters]. Bellei PM, Terra MM, Peters VM, et al. Rev. Bras. Ginecol. Obstet. 34(1), 22-7, (2012)

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[Effect of ipriflavone on growth and blood testosterone level in male rats]. Guo HJ, Li HM, and Wang CY Zhongguo Ying Yong Sheng Li Xue Za Zhi 25(2), 170-1, (2009)

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Inhibition of COX isoforms by nutraceuticals. Seaver B and Smith JR J. Herb. Pharmacother. 4(2), 11-8, (2004)

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Functionalizing mesoporous bioglasses for long-term anti-osteoporotic drug delivery. López-Noriega A, Arcos D, and Vallet-Regí M Chemistry 16(35), 10879-86, (2010)

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Effects of estrogen and estrogenic compounds on cognition in ovariectomized rats. Wu J, Zhu Y, and Wu J Climacteric 11(3), 212-20, (2008)

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Effects of enzyme inducers and inhibitors on the pharmacokinetics of intravenous ipriflavone in rats. Chung HJ, Choi YH, Kim SH, et al. J. Pharm. Pharmacol. 58(4), 449-57, (2006)

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The effect of two dietary and a synthetic phytoestrogen on transepithelial calcium transport in human intestinal-like Caco-2 cells. Cotter AA and Cashman KD Eur. J. Nutr. 44(2), 72-8, (2005)

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Identification of Hedgehog signaling inhibitors with relevant human exposure by small molecule screening. Lipinski RJ and Bushman W Toxicol. In Vitro 24(5), 1404-9, (2010)

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Pharmacokinetics of ipriflavone and its two metabolites, M1 and M5, after the intravenous and oral administration of ipriflavone to rat model of diabetes mellitus induced by streptozotocin. Lee DY, Chung HJ, Choi YH, et al. Eur. J. Pharm. Sci. 38(5), 465-71, (2009)

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Effects of water deprivation for 72 h on the pharmacokinetics of ipriflavone in rats. Chung HJ, Lee I, and Lee MG Res. Vet. Sci. 85(1), 149-55, (2008)

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Effects of ipriflavone on augmented bone using a guided bone regeneration procedure. Ito K, Minegishi T, Takayama T, et al. Clin. Oral Implants Res. 18(1), 60-8, (2007)

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Mutagenicity of ipriflavone in vivo and in vitro. Belcavello L, Vencioneck Dutra JC, de Freitas JV, et al. Food Chem. Toxicol. 50(3-4), 996-1000, (2012)

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The combination of genistin and ipriflavone prevents mammary tumorigenesis and modulates lipid profile. Hooshmand S, Khalil DA, Murillo G, et al. Clin. Nutr. 27(4), 643-8, (2008)

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Effects of E. Coli lipopolysaccharide on the pharmacokinetics of ipriflavone and its metabolites, M1 and M5, after intravenous and oral administration of ipriflavone to rats: decreased metabolism of ipriflavone due to decreased expression of hepatic CYP1A2 and 2C11. Chung HJ, Kang HE, Bae EJ, et al. J. Pharm. Sci. 97(11), 5024-36, (2008)

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Effects of ipriflavone on caged layer bone metabolism in vitro and in vivo. Yao J, Zhang J, and Hou JF Poult. Sci. 86(3), 503-7, (2007)

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Characterization of cytochrome P450s mediating ipriflavone metabolism in human liver microsomes. Moon Y, Kim SY, Ji HY, et al. Xenobiotica 37(3), 246-59, (2007)

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Ipriflavone modulates IGF-I but is unable to restore bone in rats. Deyhim F, Smith BJ, Soung DY, et al. Phytother Res. 19(2), 116-20, (2005)

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The effect of oral ipriflavone on the rat mandible during growth. Maki K, Nishida I, and Kimura M Eur. J. Orthod. 27(1), 27-31, (2005)

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Effects of phytoestrogen on mitochondrial structure and function of hippocampal CA1 region of ovariectomized rats. Xu XW, Shi C, He ZQ, et al. Cell. Mol. Neurobiol. 28(6), 875-86, (2008)

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Pharmacokinetic changes of ipriflavone in rats with acute renal failure induced by uranyl nitrate. Chung HJ and Lee MG Biopharm. Drug Dispos. 27(7), 345-51, (2006)

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Determination of ipriflavone in human plasma by LC-MS and its application in a pharmacokinetic study. Yun C, Ding L, Leng Y, et al. Biomed. Chromatogr. 26(1), 123-8, (2012)

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Determination of the anti-osteoporosis drug ipriflavone in pharmaceutical formulation by stripping voltammetric and chromatographic methods. El-Desoky HS, Beltagi AM, and Ghoneim MM J. AOAC Int. 92(3), 806-12, (2009)

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Ipriflavone pharmacokinetics in mutant Nagase analbuminemic rats. Chung HJ, Kang HE, Yang KH, et al. Biopharm. Drug Dispos. 30(6), 294-304, (2009)

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Effects of ipriflavone on postmenopausal syndrome and osteoporosis. Zhang X, Li SW, Wu JF, et al. Gynecol. Endocrinol. 26(2), 76-80, (2010)

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Potential ipriflavone and warfarin interaction. Anderson DC and Scoggins BP Am. J. Med. 120(12), e3, (2007)

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Merck 14,5074

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