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

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

Uses

1. Used in Pharmaceutical Applications:
Genistin is used as an inhibitor for protein tyrosine kinase, which plays a crucial role in various cellular processes, including cell growth, differentiation, and oncogenic transformation.
2. Used in Immune Response Applications:
Genistin is used to enhance immune reactivity against influenza viruses in vitro, potentially contributing to the development of antiviral treatments.
3. Used in Research and Analysis:
Genistin serves as an internal standard in the quantification of isoflavones, which are important for accurate and reliable measurements in various research and analytical applications.
4. Used in Cancer Research:
As a glucoside of genistein, Genistin may have potential applications in cancer research, particularly in the study of protein tyrosine kinase inhibition and its effects on cancer cell growth and proliferation.
5. Used in Bone Health Applications:
Due to its ability to promote bone marrow stromal cell and osteoblast proliferation, as well as suppress bone turnover and increase bone formation, Genistin may have potential applications in the development of treatments for bone-related conditions and the promotion of bone health.

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

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

Downstream Products

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

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.).

Two trifunctional leloir glycosyltransferases as biocatalysts for natural products glycodiversification

Two promiscuous Bacillus licheniformis glycosyltransferases, YdhE and YojK, exhibited prominent stereospecific but nonregiospecific glycosylation activity of 20 different classes of 59 structurally different natural and non-natural products. Both enzymes transferred various sugars at three nucleophilic groups (OH, NH2, SH) of diverse compounds to produce O-, N-, and S-glycosides. The enzymes also displayed a catalytic reversibility potential for a one-pot transglycosylation, thus bestowing a cost-effective application in biosynthesis of glycodiversified natural products in drug discovery.

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.

An efficient method for the glycosylation of isoflavones

The isoflavone phytoestrogens are still of current interest for their positive and negative health benefits. However, there are still many unanswered questions regarding their absorption, metabolism and bioavailability. Studies in this area require access to samples of both the isoflavone 7-O-glucosides, the form found in plants and the 7-O-glucuronides, which are important mammaliam metabolites. A new efficient, high-yielding glycosylation procedure is described for isoflavones, which employs 2,2,2-trifluoro-N-(p-methoxyphenyl) acetamidates as the glycosyl donors. This methodology was used to prepare the 7-O-glycosides of the three main isoflavones, daidzein, genistein and glycitein. The isoflavones were protected with hexanoyl groups which improved their solubility in organic solvents and improved the efficiency of the reaction. The same methodology was then adapted for the synthesis of the analogous 7-O-glucuronides. The new synthesis will provide access to large quantities of these compounds for further biological studies. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

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.

METHOD FOR PURIFYING AND SEPARATING SOY ISOFLAVONES

A method for purifying isoflavones glycosides of genistin and daidzin from impurities present in a soy isoflavones concentrate. The method includes digesting a soy isoflavones concentrate with an acidic solution and separating insoluble solids from the acidic solution, wherein the solids are enriched in genistin and comprise glycosides of genistin and daidzin.

Process for isolating genistin from mixtures of soy isoflavones

A process for enriching the relative concentration of genistin from a mixture of isoflavones is described. In accordance with one aspect of the invention, the process comprises providing a material containing a mixture of isoflavones, extracting the mater

Process for obtaining genistin-rich isoflavone composition

A process for simply and efficiently obtaining an isoflavone composition having a high ratio of genistin, which useful as a food material and the like, wherein in the process for obtaining genistin from a isoflavone inclusion, genistin is selectively precipitated by applying pH adjustment to isoflavone containing liquid.

Novel use of flavones

A pharmaceutical composition for inhibiting COX-2 biosynthesis comprising a therapeutically effective amount of the compound of formula I and a pharmaceutrically acceptable carrier. wherein R1 and R4 represent either Hydrogen or together a bond R5, R6, R7, R8 represent independently of each other Hydrogen, Hydroxy or Methoxy; in addition R7 represents a sugar substituent like glucoside, rutinosid, manno gluco pyransyl, aprosylglucoside R2 and R3 represent Hydrogen, Hydroxy, Methoxy or wherein R2′, R3′, R4′, R5′ and R6′ are independently or each other Hydrogen, Hydroxy or Methoxy with the proviso, that R2 or R3 is represented by the optionally substituted Phenylring.

Protein isolate having an increased level of isoflavone compounds and process for producing the same

The present invention relates to the production of an isoflavone enriched vegetable protein isolate in which the weight ratio of material to extractant is controlled and washing of the acid precipitated protein curd is avoided or minimized to provide an increased level of isoflavones in the protein isolate.