Genistin

Synonym(s):4′,5,7-Trihydroxyisoflavone 7-glucoside;Genistein 7-glucoside;Genistein, 7-O-β-D-Glucopyranoside;Genistein-7-O-β-D-glucopyranoside;Genistoside

CAS NO.：529-59-9
Empirical Formula: C21H20O10
Molecular Weight: 432.38
MDL number: MFCD00016883
EINECS: 610-921-5
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-19 20:33:22

What is Genistin?

Description

Genistin is a natural isoflavone isolated from legumes, including soy and kudzu. It is a phytoestrogen, as it stimulates the growth of estrogen-dependent human breast cancer cells in vivo. Like other isoflavones, genistin promotes the proliferation of bone marrow stromal cells and osteoblasts and suppresses bone turnover. It also increases bone formation in collagen matrix in vivo.

Chemical properties

White Powder

The Uses of Genistin

Genistin has been used for immune reactivity against influenza viruses in vitro and as an internal standard in isoflavones quantification.

The Uses of Genistin

A derivative of Genistein. Inhibitor

The Uses of Genistin

An isoflavone glycoside which is an inactive analog of the PTK inhibitor Genistein.

The Uses of Genistin

Glucoside of genistein that inhibits protein tyrosine kinase

What are the applications of Application

Genistin is an isoflavone glycoside which is an inactive analog of the PTK inhibitor Genistein

Definition

ChEBI: Genistein 7-O-beta-D-glucoside is a 7-hydroxyisoflavones 7-O-beta-D-glucoside. It is functionally related to a genistein. It is a conjugate acid of a genistein 7-O-beta-D-glucoside(1-).

General Description

Genistin belongs to the class of isoflavone glycosides generally extracted from soybeans.

Biochem/physiol Actions

Selective inhibitor of mammalian terminal deoxynucleotidyl transferase (TdT), with no measurable effect on mammalian or microbial DNA polymerases.

Purification Methods

Genistin is repeatedly crystallised from hot 80% EtOH/water and treated with charcoal (Nuchar) until free from saponin. The presence of saponin is detected by adding crystals to conc H2SO4 when the citron yellow colour changes to red, then purple. Pure genistin does not change colour. UV in 85% EtOH has max at 262.5nm. [Walter J Am Chem Soc 63 3273 1941, Beilstein 18 III/IV 2732.]

References

1) Uchiyama et al. (2005), Selective inhibitors of terminal deoxyribonucleotidyltransferase (TdT): baicalin and genistin; Biochim. Biophys. Acta, 1725 298 2) Choi et al. (2007), Pro-apoptotic effect and cytotoxicity of genistein and genistin in human ovarian cancer SK-OV-3 cells; Life Sci, 80 1403 3) Russo et al. (2006), Genistin inhibits UV light-induced plasmid DNA damage and cell growth in human melanoma cells; J. Nutr. Biochem., 17 103

Properties of Genistin

Melting point:	254°C
Boiling point:	256 °C
alpha	D21 -28° (c = 0.6 in 0.02N NaOH); D26 -21.4° (pyridine)
Density	1.642±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO: 10 mg/mL
form	neat
pka	6.12±0.20(Predicted)
form	Solid
color	Off-white
Merck	13,4402
BRN	64479
Stability:	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 week.

Safety information for Genistin

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.