Phenoxodiol

Names

[ Name ]:
Phenoxodiol

[Synonym ]:
2H-1-Benzopyran-7-ol, 3-(4-hydroxyphenyl)-
7-hydroxy-3-(4-hydroxy-phenyl)-2H-1-benzopyran
Haginin E
3-(4-Hydroxyphenyl)-2H-1-benzopyran-7-ol
IDRONOXIL
Phenoxodiol
Dehydroequol
3-(4-Hydroxyphenyl)-2H-chromen-7-ol
NV-06
4',7-dihydroxyisoflav-3-ene
4',7-dihydroxy-3-phenyl-3,4-dehydrochroman

Biological Activity

[Description]:

Phenoxodiol, a synthetic analog of Genestein, activates the mitochondrial caspase system, inhibits XIAP (an apoptosis inhibitor), and sensitizes the cancer cells to Fas-mediated apoptosis. This agent also inhibits DNA topoisomerase II by stabilizing the cleavable complex. Phenoxodiol induces cell cycle arrest in the G1/S phase of the cell cycle and upregulates p21WAF1 via a p53 independent manner[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase

Signaling Pathways >> Apoptosis >> Caspase

[Target]

Caspase, DNA topoisomerase II[1][2].

[References]

[1]. Kamsteeg M, et al. Phenoxodiol--an isoflavone analog--induces apoptosis in chemoresistant ovarian cancer cells. Oncogene. 2003 May 1;22(17):2611-20.

[2]. Mahoney S, et al. The effects of phenoxodiol on the cell cycle of prostate cancer cell lines. Cancer Cell Int. 2014 Nov 8;14(1):110.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
463.7±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₅H₁₂O₃

[ Molecular Weight ]:
240.254

[ Flash Point ]:
234.3±28.7 °C

[ Exact Mass ]:
240.078644

[ PSA ]:
49.69000

[ LogP ]:
4.35

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.679

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H400

[ Precautionary Statements ]:
P273

[ Hazard Codes ]:
Xi

[ RIDADR ]:
UN 3077 9 / PGIII

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Involvement of a Hydrophobic Pocket and Helix 11 in Determining the Modes of Action of Prenylated Flavonoids and Isoflavonoids in the Human Estrogen Receptor.

ChemBioChem. 16 , 2668-77, (2016)

Six prenylated (iso)flavonoids were purified from a licorice root extract and subjected to competition experiments with six commercially available (iso)flavonoids. The agonistic and antagonistic activ...

Enhancement of the activity of phenoxodiol by cisplatin in prostate cancer cells.

Br. J. Cancer 100 , 649-655, (2009)

Phenoxodiol is a novel isoflav-3-ene, currently undergoing clinical trials, that has a broad in vitro activity against a number of human cancer cell lines. Phenoxodiol alone inhibited DU145 and PC3 in...

Pharmacokinetics of phenoxodiol, a novel isoflavone, following intravenous administration to patients with advanced cancer.

BMC Clin. Pharmacol. 11 , 1, (2011)

Phenoxodiol is a novel isoflavone currently being studied in clinical trials for the treatment of cancer. This study reports the pharmacokinetics of phenoxodiol in patients with cancer.The pharmacokin...

Related Compounds

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