6,7,4'-Trihydroxyisoflavone

Modify Date: 2024-01-06 10:44:23

6,7,4'-Trihydroxyisoflavone structure	Common Name	6,7,4'-Trihydroxyisoflavone
	CAS Number	17817-31-1	Molecular Weight	270.23700
	Density	1.548g/cm3	Boiling Point	587.1ºC at 760mmHg
	Molecular Formula	C₁₅H₁₀O₅	Melting Point	N/A
	MSDS	N/A	Flash Point	229.7ºC

Use of 6,7,4'-Trihydroxyisoflavone

Desmethylglycitein (4',6,7-Trihydroxyisoflavone), a metabolite of daidzein, sourced from Glycine max with antioxidant, and anti-cancer activities.Desmethylglycitein binds directly to CDK1 and CDK2 in vivo, resulting in the suppresses CDK1 and CDK2 activity[1]. Desmethylglycitein is a direct inhibitor of protein kinase C (PKC)α, against solar UV (sUV)-induced matrix matrix metalloproteinase 1 (MMP1)[2]. Desmethylglycitein binds to PI3K in an ATP competitive manner in the cytosol, where it inhibits the activity of PI3K and downstream signaling cascades, leading to the suppression of adipogenesis in 3T3-L1 preadipocytes[3].

Name	4',6,7-trihydroxyisoflavone
Synonym	More Synonyms

Description	Desmethylglycitein (4',6,7-Trihydroxyisoflavone), a metabolite of daidzein, sourced from Glycine max with antioxidant, and anti-cancer activities.Desmethylglycitein binds directly to CDK1 and CDK2 in vivo, resulting in the suppresses CDK1 and CDK2 activity[1]. Desmethylglycitein is a direct inhibitor of protein kinase C (PKC)α, against solar UV (sUV)-induced matrix matrix metalloproteinase 1 (MMP1)[2]. Desmethylglycitein binds to PI3K in an ATP competitive manner in the cytosol, where it inhibits the activity of PI3K and downstream signaling cascades, leading to the suppression of adipogenesis in 3T3-L1 preadipocytes[3].
Related Catalog	Signaling Pathways >> Epigenetics >> PKC Research Areas >> Cancer Signaling Pathways >> PI3K/Akt/mTOR >> PI3K Signaling Pathways >> Cell Cycle/DNA Damage >> CDK Signaling Pathways >> TGF-beta/Smad >> PKC
Target	CDK1 CDK2 PKC
In Vitro	Desmethylglycitein (4',6,7-Trihydroxyisoflavone)(0-100 μM; 24-72 hours) suppesses anchorage-dependent growth of HCT-116 and DLD1 cells in a dose- and time-dependent manner without cytotoxicity [1]. Desmethylglycitein (4',6,7-Trihydroxyisoflavone)(0-100 μM; 24-72 hours) suppresses CDK1 activity in a dose-dependent manner and inhibits CDK2 activity in HCT-116 cells[1]. Desmethylglycitein (4',6,7-Trihydroxyisoflavone)(0-100 μM; 24-72 hours) induces cell cycle arrest at the S and G2/M phases, the percentage of cells in S phase is higher in the 100 μM 6,7,4′-THIF-treated group, and the same pattern is observed in G2/M phase (29.5% versus 19.1% ) [1]. Cell Viability Assay[1] Cell Line: HCT-116 cells Concentration: 0, 12.5, 25, 50 or 100 μM Incubation Time: 24, 48 or 72 hours Result: Inhibited anchorage-dependent and -independent growth of HCT-116 cells. Western Blot Analysis[1] Cell Line: HCT-116 and DLD1 cells Concentration: 0, 25, 50 or 100 μM Incubation Time: 48 hours Result: Inhibited CDK1,CDK2 expression. Cell Cycle Analysis[1] Cell Line: HCT-116 cells Concentration: 0, 25, 50 or 100 μM Incubation Time: 24, 48 or 72 hours Result: Induces cell cycle arrest of HCT-116 cells at S and G2/M phases.
In Vivo	Desmethylglycitein (4',6,7-Trihydroxyisoflavone) (intraperitoneally injection; 5 or 25 mg/kg; once daily; 20 days) suppresses tumor development in mice and serves as an effective anticancer treatment with the potential to inhibit or delay the tumorigenicity of HCT-116 cells in an in vivo system[1]. Animal Model: Female athymic nude mice subcutaneously injected with HCT-116 cells[1] Dosage: 5 or 25 mg/kg Administration: Intraperitoneally injection; 5 or 25 mg/kg; once daily; 20 days Result: Decreased tumor growth, volume and weight of HCT-116 xenografts.
References	[1]. Lee DE, et al. 6,7,4'-trihydroxyisoflavone inhibits HCT-116 human colon cancer cell proliferation by targeting CDK1 and CDK2. Carcinogenesis. 2011 Apr;32(4):629-35. [2]. Lim TG, et al. The daidzein metabolite, 6,7,4'-Trihydroxyisoflavone, is a novel inhibitor of PKCα in suppressing solar UV-induced matrix metalloproteinase 1. Int J Mol Sci. 2014 Nov 19;15(11):21419-32 [3]. Seo SG, et al. A metabolite of daidzein, 6,7,4'-trihydroxyisoflavone, suppresses adipogenesis in 3T3-L1 preadipocytes via ATP-competitive inhibition of PI3K.

Density	1.548g/cm3
Boiling Point	587.1ºC at 760mmHg
Molecular Formula	C₁₅H₁₀O₅
Molecular Weight	270.23700
Flash Point	229.7ºC
Exact Mass	270.05300
PSA	90.90000
LogP	2.57680
Vapour Pressure	2.21E-14mmHg at 25°C
Index of Refraction	1.732

Safety Phrases	22-24/25
WGK Germany	3
HS Code	2914501900

Daidzein

CAS#:486-66-8

6,7,4'-Trihydro...

CAS#:17817-31-1

Literature: Phytochemistry, , vol. 34, # 4 p. 979 - 981

Glycitein

CAS#:40957-83-3

~30%

6,7,4'-Trihydro...

CAS#:17817-31-1

Literature: Klus; Borger-Papendorf; Barz Phytochemistry, 1993 , vol. 34, # 4 p. 979 - 981

1-(2,4,5-trihyd...

CAS#:76095-37-9

N,N-Dimethylfor...

CAS#:68-12-2

~51%

6,7,4'-Trihydro...

CAS#:17817-31-1

Literature: Vasquez-Martinez, Yesseny; Ohri, Rachana V.; Kenyon, Victor; Holman, Theodore R.; Sepulveda-Boza, Silvia Bioorganic and Medicinal Chemistry, 2007 , vol. 15, # 23 p. 7408 - 7425

s-triazine

CAS#:290-87-9

1-(2,4,5-trihyd...

CAS#:76095-37-9

~59%

6,7,4'-Trihydro...

CAS#:17817-31-1

Literature: Jah, Hem Chandra; Zilliken, Fritz; Breitmaier, Eberhard Angewandte Chemie, 1981 , vol. 93, # 1 p. 129 - 130

Methanol

CAS#:67-56-1

Daidzein

CAS#:486-66-8

~40%

6,7,4'-Trihydro...

CAS#:17817-31-1

Glycitein

CAS#:40957-83-3

Literature: Phytochemistry, , vol. 34, # 4 p. 979 - 981

Daidzein

CAS#:486-66-8

~40%

6,7,4'-Trihydro...

CAS#:17817-31-1

Glycitein

CAS#:40957-83-3

Literature: Phytochemistry, , vol. 34, # 4 p. 979 - 981

Precursor 5
CAS#:486-66-8 Daidzein CAS#:40957-83-3 Glycitein CAS#:68-12-2 N,N-Dimethylfor... CAS#:290-87-9 s-triazine
CAS#:67-56-1 Methanol
DownStream 4
CAS#:550-79-8 Afrormosine CAS#:40957-83-3 Glycitein CAS#:970-48-9 4',7-DIMETHOXY-... CAS#:798-61-8 4',6,7-Trimetho...

HS Code	2914501900
Summary	2914501900 other ketone-phenols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%