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3',4',7-trihydroxy isoflavone

Names

[ CAS No. ]:
485-63-2

[ Name ]:
3',4',7-trihydroxy isoflavone

[Synonym ]:
7,3',4'-THIF
3-(3,4-Dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one
3',4',7-Trihydroxyisoflavone
3`,4`,7-Trihydroxyisoflavone
4H-1-Benzopyran-4-one, 3-(3,4-dihydroxyphenyl)-7-hydroxy-
3l5r
MFCD00143002
3-(3,4-Dihydroxy-phenyl)-7-hydroxy-chromen-4-on
3',4',7-trihydroxy isoflavone
3'-Hydroxydaidzein
3-(3,4-dihydroxyphenyl)-7-hydroxychromen-4-one
3-(3,4-dihydroxy-phenyl)-7-hydroxy-chromen-4-one
7,3',4'-Trihydroxyisoflavone
7-Hydroxy-3-(3,4-dihydroxyphenyl)-4H-chromen-4-one
4H-1-Benzopyran-4-one,3-(3,4-dihydroxyphenyl)-7-hydroxy

Biological Activity

[Description]:

7,3',4'-Trihydroxyisoflavone, a major metabolite of Daidzein, is an ATP-competitive inhibitor of Cot (Tpl2/MAP3K8) and MKK4. 7,3',4'-Trihydroxyisoflavone has anticancer, anti-angiogenic, chemoprotective, and free radical scavenging activities[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> MAPK/ERK Pathway >> MAP3K

[In Vitro]

7,3',4'-Trihydroxyisoflavone triggers cell cycle arrest at the G1 phase and displays an anti-proliferative effect against EGF receptor-positive skin cancer[1]. 7,3',4'-Trihydroxyisoflavone also significantly inhibits UVB-induced COX-2 expression by suppressing the NF-B transcription activity in mouse skin epidermal JB6 P+ cells[1].

[In Vivo]

In a mouse skin tumorigenesis model, 7,3',4'-Trihydroxyisoflavone strongly suppresses the incidence, multiplicity, and volume of UVB-induced mouse skin tumors. Consistent with the tumor data, 7,3',4'-Trihydroxyisoflavone clearly attenuates UVB-induced COX-2 expression in hairless mouse skin[2].

[References]

[1]. Yu-Li Lo, et al. 7,3',4'-Trihydroxyisoflavone modulates multidrug resistance transporters and induces apoptosis via production of reactive oxygen species. Toxicology. 2012 Dec 16;302(2-3):221-32.

[2]. Dong Eun Lee, et al. 7,3',4'-Trihydroxyisoflavone, a metabolite of the soy isoflavone daidzein, suppresses ultraviolet B-induced skin cancer by targeting Cot and MKK4. J Biol Chem. 2011 Apr 22;286(16):14246-56.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
572.8±50.0 °C at 760 mmHg

[ Melting Point ]:
280-282°C

[ Molecular Formula ]:
C15H10O5

[ Molecular Weight ]:
270.24

[ Flash Point ]:
224.0±23.6 °C

[ Exact Mass ]:
270.052826

[ PSA ]:
90.90000

[ LogP ]:
2.58

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.732

[ Storage condition ]:
-20°C Freezer

[ Stability ]:
Store in Freezer

Safety Information

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S24/25

[ WGK Germany ]:
3

Synthetic Route

Precursor & DownStream


Related Compounds