Genistin

Genistin Basic information
Product Name:Genistin
Synonyms:4',5,7-TRIHYDROXYISOFLAVONE 7-GLUCOSIDE;7-O-B-D-GLUCOPRYANOSYL GENISTEIN;7-O-BETA-D-GLUCOPYRANOSIDE;GENISTEIN, 7-O-BETA-D-GLUCOPYRANOSIDE;GENISTIN;GLUCOSYL-7-GENISTEIN;4μ,5,7-Trihydroxyisoflavone 7-glucoside, Genistein 7-glucoside, Genistein-7-O-β-D-glucopyranoside;Genistin,Genistein 7-glucoside
CAS:529-59-9
MF:C21H20O10
MW:432.38
EINECS:610-921-5
Product Categories:Iso-Flavones;The group of Daidzin;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product;Inhibitors;inhibitor;Aromatics;Glucuronides;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:529-59-9.mol
Genistin Structure
Genistin Chemical Properties
Melting point 254°C
alpha D21 -28° (c = 0.6 in 0.02N NaOH); D26 -21.4° (pyridine)
Boiling point 256 °C
density 1.642±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: 10 mg/mL
pka6.12±0.20(Predicted)
form neat
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.
InChIKeyZCOLJUOHXJRHDI-CMWLGVBASA-N
LogP0.790 (est)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
RTECS DJ3093000
10
HS Code 29389090
MSDS Information
ProviderLanguage
SigmaAldrich English
Genistin Usage And Synthesis
DescriptionGenistin 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 PropertiesWhite Powder
UsesGenistin has been used for immune reactivity against influenza viruses in vitro and as an internal standard in isoflavones quantification.
UsesA derivative of Genistein. Inhibitor
UsesGlucoside of genistein that inhibits protein tyrosine kinase
UsesAn isoflavone glycoside which is an inactive analog of the PTK inhibitor Genistein.
DefinitionChEBI: 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 DescriptionGenistin belongs to the class of isoflavone glycosides generally extracted from soybeans.
Biochem/physiol ActionsSelective inhibitor of mammalian terminal deoxynucleotidyl transferase (TdT), with no measurable effect on mammalian or microbial DNA polymerases.
Purification MethodsGenistin 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.]
References1) 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
Genistin Preparation Products And Raw materials
Preparation ProductsSophoricoside
Bengenin Baicalin Glycitein GENISTIN(RG) Tectoridin Alkyl polyglucoside GENISTIN(RG)(CALL) Isoflavone Genistin-D4 (4-Hydroxyphenyl-2,3,5,6-D4) GENISTIN SNAP-N-SHOOT 0.1mg/ml(P) BETA-GLUCOSIDASE GENISTIN(SH) Evodiamine,Ecdysterone,Fistein,Genistin,Genistein 6''-O-ACETYLGENISTIN GENISTIN(P) GENISTEIN 7-O-APIOSYL-(1,6)-GLUCOSIDE kakkalide OCTYL GLUCOSIDE

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