529-59-9

Basic information

• Product Name: Genistin
• Synonyms: 7-(-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;Genistein-7--O-Glucopyranoside;4μ,5,7-Trihydroxyisoflavone 7-glucoside, Genistein 7-glucoside, Genistein-7-O-β-D-glucopyranoside;Genistin，Genistein 7-glucoside;7-[(β-D-Glucopyranosyl)oxy]-4',5-dihydroxyisoflavone;Genistin ,98%;Genistin,4′,5,7-Trihydroxyisoflavone 7-glucoside, Genistein 7-glucoside, Genistein-7-O-β-D-glucopyranoside;Genistin (30 mg)
• CAS NO: 529-59-9
• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.38
• EINECS: 1308068-626-2
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Glucuronides;Heterocycles;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;inhibitor;natural product;Inhibitors;Iso-Flavones;The group of Daidzin
• Mol File: 529-59-9.mol
• Article Data: 15

Chemical Properties

• Melting Point: 254°C
• Boiling Point: 788.9 °C at 760 mmHg
• Flash Point: 280.7 °C
• Appearance: White powder
• Density: 1.642 g/cm³
• Vapor Pressure: 3.14E-26mmHg at 25°C
• Refractive Index: 1.717
• Storage Temp.: −20°C
• Solubility: DMSO: 10 mg/mL
• PKA: 6.12±0.20(Predicted)
• 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.
• Merck: 13,4402
• BRN: 64479
• CAS DataBase Reference: Genistin(CAS DataBase Reference)
• NIST Chemistry Reference: Genistin(529-59-9)
• EPA Substance Registry System: Genistin(529-59-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: DJ3093000
• F: 10
• Hazardous Substances Data: 529-59-9(Hazardous Substances Data)

Usage

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

Uses

Different sources of media describe the Uses of 529-59-9 differently. You can refer to the following data:
1. A derivative of Genistein. Inhibitor
2. An isoflavone glycoside which is an inactive analog of the PTK inhibitor Genistein.
3. Genistin has been used for immune reactivity against influenza viruses in vitro and as an internal standard in isoflavones quantification.
4. Glucoside of genistein that inhibits protein tyrosine kinase

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

InChI:InChI=1/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2

Upstream product

• 133-89-1 UDP-glucose 
• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 
• 76298-37-8 5,4'-di-O-acetylgenistein-7-yl 2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranoside 
• 1105697-82-2 5,4'-di-O-hexanoylgenistein-7-yl 2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranoside 
• 51011-05-3 6''-O-malonylgenistin 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 73566-30-0 genistein-7-O-β-D-(6''-O-acetylglucopyranoside) 
• 67-56-1 methanol 

Downstream Products

• 486-66-8 daidzein 
• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 
• 50-99-7 D-glucose 
• 2280-44-6 D-Glucose 

Relevant articles and documents

Identification of a flavonoid 7-O-glucosyltransferase from Andrographis paniculata

Andrographis paniculata is an important traditional medicinal herb in which flavonoids are part of the primary specialized metabolites. A flavonoid glucosyltransferase with broad substrate spectrum (named ApUGT3) was successfully identified by screening homologous glycosyltransferase genes from A. paniculata. The enzyme displayed glycosylation activity toward multiple flavonoids in?vitro, and the major products were identified as 7-O-glucosides. Phylogenetic analysis revealed that ApUGT3 is the first reported glycosyltransferase from the Acanthaceae family that belongs to cluster I, suggesting that ApUGT3 is a new flavonoid glycosyltransferase of this subcluster. This enzyme is potentially useful as powerful glycosylation catalysts to modify flavonoid-like compounds and improve their biological activities. (Figure presented.).

Microbial glycosylation of daidzein, genistein and biochanin a: Two new glucosides of biochanin A

Biotransformation of daidzein, genistein and Biochanin A by three selected filamentous fungi was investigated. As a result of biotransformations, six glycosylation products were obtained. Fungus Beauveria bassiana converted all tested isoflavones to 4″-O-methyl-7-O-glucosyl derivatives, whereas Absidia coerulea and Absidia glauca were able to transform genistein and Biochanin A to genistin and sissotrin, respectively. In the culture of Absidia coerulea, in addition to the sissotrin, the product of glucosylation at position 5 was formed. Two of the obtained compounds have not been published so far: 4″-O-methyl-7-O-glucosyl Biochanin A and 5-O-glucosyl Biochanin A (isosissotrin). Biotransformation products were obtained with 22%-40% isolated yield.

Kinetic modeling of malonylgenistin and malonyldaidzin conversions under alkaline conditions and elevated temperatures

The conversion and degradation of malonylglucosides were kinetically characterized under elevated pH/heat conditions. Malonylgenistin and malonyldaidzin were heated at 60, 80, and 100°C and pH values of 8.5, 9, and 9.5. A simple kinetic model was developed, which adequately predicted the conversion and degradation reactions. The conversion and degradation rates increased as temperature and pH increased. The rates of conversion of both malonylglucosides into their respective β-glucosides were comparable under all pH/heat treatments. However, at 100°C, the rates of degradation of malonyldaidzin were approximately double those of malonylgenistin, under all pH treatments. When malonlydaidzin was heated at 100°C and pH 9.5, degradation of the produced daidzin occurred. Therefore, an alternative kinetic model was developed to better predict the conversion and degradation of malonyldaidzin occurring at 100°C and pH 9.5. The models developed provide soy food manufacturers with guidelines for better control of the profile and level of isoflavones.