Home Cart Sign in  
Chemical Structure| 446-72-0 Chemical Structure| 446-72-0
Chemical Structure| 446-72-0

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

Genistein has multiple biological functions. It can inhibit several tyrosine kinases (IC50 of 0.6 μM for EGFR), inhibits DNA topoisomerase-II and activation of PPARs. Genistein is a phytoestrogen which has selective estrogen receptor modulator properties.

Synonyms: NPI 031L; CI-75610; BIO300

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of Genistein

CAS No. :446-72-0
Formula : C15H10O5
M.W : 270.24
SMILES Code : O=C1C(C2=CC=C(O)C=C2)=COC3=C1C(O)=CC(O)=C3
Synonyms :
NPI 031L; CI-75610; BIO300
MDL No. :MFCD00016952
InChI Key :TZBJGXHYKVUXJN-UHFFFAOYSA-N
Pubchem ID :5280961

Safety of Genistein

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Genistein

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 446-72-0 ]

[ 446-72-0 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 446-72-0 ]
  • [ 572-09-8 ]
  • [ 529-59-9 ]
  • 5-Hydroxy-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-[4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-chromen-4-one [ No CAS ]
  • 2
  • [ 152-95-4 ]
  • [ 446-72-0 ]
  • 3
  • [ 529-59-9 ]
  • [ 50-99-7 ]
  • [ 446-72-0 ]
  • 4
  • [ 529-59-9 ]
  • [ 2280-44-6 ]
  • [ 446-72-0 ]
  • 5
  • [ 529-59-9 ]
  • [ 446-72-0 ]
YieldReaction ConditionsOperation in experiment
99% In hydrogenchloride; D. Hydrolysis and Crystallization: About 1578 mg of <strong>[529-59-9]genistin</strong> were refluxed in 960 ml 4N HCl for five hours at 100+-5 C. About 948 mg genistein were obtained with about 96% recovery. 483.2 mg of genistein (99% purity) recovered from the hydrolysis step was dissolved in 450 ml methanol and crystallized in 20 ml methanol. About 373.8 mg of genistein crystal was obtained giving a 77% recovery and 99.5% purity. Genistein m.p. 298.4-299.9 C. 1 H NMR (400 MHz, DMSO-d6) 6.22 (1H, d, J=2 Hz, H-8), 6.38 (1H, d, J=2 Hz, H-6), 6.83 (2H, d, J=8 Hz, H-3'), 7.39 (2H, d, J=8 Hz, H-2'), 8.43 (1H, s, H-2), 9.61 (1H, s, 4'-OH), 10.90 (1H, s, 7-OH) 12.92 (1H, s, 5-OH). 13 C NMR (100 MHz, DMSO-d6) 154.5, 122.8, 180.7, 162.5, 99.5, 164.8, 94.2, 157.9, 105.0, 121.7, 130.7, 115.6, 158.1.
In hydrogenchloride; D. Genistein via Hydrolysis and Crystallization: About 49.0 mg of <strong>[529-59-9]genistin</strong> were refluxed in 15 ml 4N HCl for five hours at 105+-5 C. About 22.9 mg of genistein was obtained with about 75% recovery. About 13 mg genistein from the previous step was extracted twice with 50 ml diethyl ether. The extracts were combined, and evaporated to dryness. The solids obtained were crystallized from 2 ml of a solution made from 3 parts ethanol and 2 parts water. About 8.2 mg of the genistein crystal was obtained with 63% recovery and about 99% purity.
  • 7
  • [ 446-72-0 ]
  • [ 1450-93-7 ]
  • [ 1357294-57-5 ]
  • 8
  • [ 446-72-0 ]
  • Absidia coerulea AM 93 [ No CAS ]
  • [ 529-59-9 ]
YieldReaction ConditionsOperation in experiment
12.5% In dimethyl sulfoxide; for 240h;Large scale; Enzymatic reaction; General procedure: Portions of 1.5 mL of the 3-day inoculation culture were transferred to 300 mL Erlenmeyer flasks,each containing 100 mL of the medium. In the preparative (large scale) biotransformation, a total of60 mg of each substrate dissolved in 6 mL of DMSO and was equally distributed among four flasks with4-day fungal cultures to give a final concentration of 150 mg/L. After 10 days of incubation, the cultureswere acidified with 1 M HCl to pH around 5 and three time extracted with the same volume of ethylacetate. The other procedures and culture conditionswere the same as those of the screening experiments.The collected organic phase was dried over anhydrous MgSO4, the solvent was filtered, evaporatedin a vacuum and analyzed using TLC and HPLC. The biotransformation products were separated bycolumn chromatography on silica gel 60 (230-400 mesh,Merck, Darmstadt, Germany) using chloroform:methanol (3:1 v/v) as eluent. TLC was carried out with Merck silica gel 60, F254 (0.2 mm thick)plates using the same eluents. Products were detected by inspecting plates under UV irradiation.Rf: 0.53 (genistin); 0.64 (sissotrin, isosissotrin); 0.77 (4?-O-methyldaidzin); 0.79 (4?-O-methylgenistin);0.84 (4?-O-methylsissotrin); 0.85 (genistein); 0.87 (daidzein); 0.89 (biochanin A).
  • 9
  • [ 446-72-0 ]
  • Absidia glauca AM 177 [ No CAS ]
  • [ 529-59-9 ]
YieldReaction ConditionsOperation in experiment
21.9% In dimethyl sulfoxide; for 240h;Large scale; Enzymatic reaction; General procedure: Portions of 1.5 mL of the 3-day inoculation culture were transferred to 300 mL Erlenmeyer flasks,each containing 100 mL of the medium. In the preparative (large scale) biotransformation, a total of60 mg of each substrate dissolved in 6 mL of DMSO and was equally distributed among four flasks with4-day fungal cultures to give a final concentration of 150 mg/L. After 10 days of incubation, the cultureswere acidified with 1 M HCl to pH around 5 and three time extracted with the same volume of ethylacetate. The other procedures and culture conditionswere the same as those of the screening experiments.The collected organic phase was dried over anhydrous MgSO4, the solvent was filtered, evaporatedin a vacuum and analyzed using TLC and HPLC. The biotransformation products were separated bycolumn chromatography on silica gel 60 (230-400 mesh,Merck, Darmstadt, Germany) using chloroform:methanol (3:1 v/v) as eluent. TLC was carried out with Merck silica gel 60, F254 (0.2 mm thick)plates using the same eluents. Products were detected by inspecting plates under UV irradiation.Rf: 0.53 (genistin); 0.64 (sissotrin, isosissotrin); 0.77 (4?-O-methyldaidzin); 0.79 (4?-O-methylgenistin);0.84 (4?-O-methylsissotrin); 0.85 (genistein); 0.87 (daidzein); 0.89 (biochanin A).
  • 10
  • [ 446-72-0 ]
  • [ 15839-70-0 ]
  • genistein fucoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
With magnesium(II) chloride hexahydrate; glycosyltransferase from Arabidopsis thaliana; In aq. buffer; at 37.0℃; for 3h;pH 7.5;Enzymatic reaction; General procedure: After checking the expression of protein, glycosylation reactions were carriedout using crude protein (AtUGT89C1) with genistein and sugars (T/UDP-α-Dglucose,UDP-α-D-galactose, UDP-α-D-glucuronic acid, UDP-α-D-N-acetyl-Dglucosamine,UDP-α-DN-acetylgalactosamine, dTDP-β-L-rhamnose, dTDP-α-2-deoxy-D-glucose, and <strong>[15839-70-0]GDP-β-L-fucose</strong>) as sugar donors. The reaction was carriedout in a total volume of 200 μL containing 100mMTris-HCl (pH 7.5) buffer, 2mMNDP sugar, 2 mM genistein, 10 mM MgCl2. 6H2 O, and 30 μL of crude protein(enzyme concentration was not calculated). The reaction mixtures were incubatedat 37C for 3 h. The reaction mixture lacking enzyme served as the control. Thereactionwas quenched by adding 400 μL chilled methanol and vortexing for severalminutes. Aliquots were centrifuged at 16,000×g to remove denatured proteins, andthe reaction products were monitored by HPLC coupled with a photodiode array(PDA), with 20 μL injected after proper dilution.
  • 11
  • [ 133-89-1 ]
  • [ 446-72-0 ]
  • [ 529-59-9 ]
YieldReaction ConditionsOperation in experiment
With flavonoid 7-O-glucosyltransferase from Andrographis paniculata; In methanol; at 30℃; for 12h;Enzymatic reaction; General procedure: All assays and incubations were performed in 100 ll of 50mM Tris-HCl (pH 8.0)containing 8 lg of purified proteins, 200 lM aglycone, and 3200 lM UDP-glucose.The reactions were incubated at 30 C for 12 h and terminated by the addition of200 ll of methanol. The products of the reactions were filtered through a 0.22-lmnylon syringe filter and analyzed using a Waters Acquity UPLC-I-Class system(Waters Corp., Milford, MA) with an Acquity UPLC BEH C18 column (1.7 mm,2.1mm 50 mm). The column temperature was set to 40 C, and the flow rate was400 lL/min. Mobile phase A was a 0.1% formic acid aqueous solution, and mobilephase B was acetonitrile. Gradient programs were used to analyze the reaction mixtures(Table 1). The total conversion rate was calculated to be one percent of the sumof the peak areas of the substrate and product(s). The experiment was performed inthe ESI (-) mode as previously described [17].
  • 12
  • [ 133-89-1 ]
  • [ 446-72-0 ]
  • [ 152-95-4 ]
  • [ 529-59-9 ]
  • Genistein 7-O-β-D-glucopyranoside-4'-O-β-D-glucopyranoside [ No CAS ]
 

Historical Records

Categories