6,7,4'-Trihydroxyisoflavone

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

6,7,4'-Trihydroxyisoflavone Structure
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].

 Names

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

 6,7,4'-Trihydroxyisoflavone Biological Activity

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
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.

 Chemical & Physical Properties

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 Information

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

 Synthetic Route

~%

6,7,4'-Trihydroxyisoflavone Structure

6,7,4'-Trihydro...

CAS#:17817-31-1

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

~30%

6,7,4'-Trihydroxyisoflavone Structure

6,7,4'-Trihydro...

CAS#:17817-31-1

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

~51%

6,7,4'-Trihydroxyisoflavone Structure

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

~59%

6,7,4'-Trihydroxyisoflavone Structure

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

~40%

6,7,4'-Trihydroxyisoflavone Structure

6,7,4'-Trihydro...

CAS#:17817-31-1

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

~40%

6,7,4'-Trihydroxyisoflavone Structure

6,7,4'-Trihydro...

CAS#:17817-31-1

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

 Customs

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%

 Synonyms

Demethyltexasin
6,7,4'-trihydroxyisoflavone
6,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
4',6,7-trihydroxy-isoflavone
6-hydroxydaidziein
6-Hydroxydaidzein
MFCD00016953
6,7,4'-trihydroxyisoflavon
6,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one