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529-59-9

529-59-9 structure
529-59-9 structure
  • Name: Genistin
  • Chemical Name: genistein 7-O-β-D-glucoside
  • CAS Number: 529-59-9
  • Molecular Formula: C21H20O10
  • Molecular Weight: 432.378
  • Catalog: Biochemical Natural product
  • Create Date: 2018-10-02 19:24:44
  • Modify Date: 2024-01-02 22:49:25
  • Genistin is the major isoflavonoid of soybeans and soy products.
Name genistein 7-O-β-D-glucoside
Synonyms 7-(b-D-Glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
5-Hydroxy-3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-on
Genisteol 7-monoglucoside
Genistin
5-Hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl-β-D-glucopyranoside
4H-1-Benzopyran-4-one, 7-(β-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-
4',5,7-trihydroxyisoflavone-7-D-glucoside
Diadzin
MFCD00016883
4',5,7-Trihydroxyisoflavone 7-glucoside
GLUCOSYL-7-GENISTEIN
Genistein-7-glucoside
genistein 7-O-beta-D-glucoside
Genistein 7-O-β-D-glucoside
Genistein, 7-O-β-D-glucoside
genistein 7-O-glucoside
5-Hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl β-D-glucopyranoside
Genistein 7-O-b-D-Glucoside
Soybean Extract
5-Hydroxy-3-(4-hydroxyphényl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}-4H-chromén-4-one
Genistein-7-O-β-D-glucopyranoside
Genistine
Genistein glucoside
Genistoside
Genistein, 7-β-D-glucopyranoside
5-Hydroxy-3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-one
4H-1-Benzopyran-4-one, 7- (β-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-
Genistein-7-O-glucoside
Genistein 7-glucoside
Description Genistin is the major isoflavonoid of soybeans and soy products.
Related Catalog
In Vitro Genistin is the major isoflavonoid of soybeans and soy products. Genistin shows a dose-dependent superoxide scavenging effect and exhibits major effect at 200 μM, corresponding in activity to 0.08 U/mg protein superoxide dismutase (SOD). Results demonstrate that Genistin exhibits a significantly (P<0.01) and a dose-dependent inhibitory effect on the human cancer cell examined, and at higher concentration (100 μM), the cell viability is 59%. Genistin also induces a significant and dose-dependent increase in ROS formation when compare with the untreated control[1].
In Vivo Myocardial infarct is markedly diminished by pretreatment with Genistin, particularly at the high dose. After 1 h of reperfusion, preconditioning with Genistin at dosages of 20 to 60 mg/kg significantly attenuats the release of lactate dehydrogenase (LDH), creatine kinase (CK) in a dose-dependent manner compare with the I/R group. Results show that the level of malondialdehyde (MDA) is decreased and the activities of superoxide dismutase (SOD) and catalase (CAT) are increased as well as an increased glutathione (GSH) level in a dose-dependent manner by Genistin treatment in I/R. Pretreatment with Genistin (20, 40 and 60 mg/kg) also prevents the expression of P2X7, p-IκBα, and p-NF-κB p65 compare with the model group[2].
Cell Assay M14 human melanoma cells are used and grown in RPMI containing 10% fetal calf serum, 100 U/mL penicillin, 100 μg/mL streptomycin, and 25 μg/mL fungizone. After 24 h of incubation at 37°C under a humidified 5% carbon dioxide to allow cell attachment, the cells are treated with different concentrations (12, 25, 50, and 100 μM) of Genistin and daidzin, and incubated for 72 h under the same conditions[1].
Animal Admin Sprague-Dawley rats (male, 250 to 300 g) are used to establish the I/R injury animal model and used in this experiment. Rats are randomly apportioned in equal animals (n=10) to five experimental groups: (1) sham group: rats are subjected to the entire surgical procedure but without the induction of I/R; (2) model group: I/R injury animal model is constructed by left anterior descending coronary artery (LAD) ligation for 30 min, and then the LAD is allowed 1 h reperfusion; and (3) three Genistin-treated groups: different doses (20, 40, and 60 mg/kg body weight, resp.) of Genistin dissolved in 0.5% sodium carboxyl methyl cellulose (CMC-Na) solution are given intragastrically for 5 days before operation[2].
References

[1]. Russo A, et al. Genistin inhibits UV light-induced plasmid DNA damage and cell growth in human melanoma cells. J Nutr Biochem. 2006 Feb;17(2):103-8.

[2]. Gu M, et al. Cardioprotective Effects of Genistin in Rat Myocardial Ischemia-Reperfusion Injury Studies by Regulation of P2X7/NF-κB Pathway. Evid Based Complement Alternat Med. 2016;2016:5381290.
Density 1.6±0.1 g/cm3
Boiling Point 788.9±60.0 °C at 760 mmHg
Melting Point 254ºC
Molecular Formula C21H20O10
Molecular Weight 432.378
Flash Point 280.7±26.4 °C
Exact Mass 432.105652
PSA 170.05000
LogP 0.79
Vapour Pressure 0.0±2.9 mmHg at 25°C
Index of Refraction 1.717

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DJ3093000
CHEMICAL NAME :
4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-
CAS REGISTRY NUMBER :
529-59-9
BEILSTEIN REFERENCE NO. :
0064479
LAST UPDATED :
199612
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C21-H20-O10
MOLECULAR WEIGHT :
432.41

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 13,51,1979
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS DJ3093000

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