Genistein
- CAS No.
- 446-72-0
- Chemical Name:
- Genistein
- Synonyms
- Licoisoflavone;5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one;GEN;GENESTEIN;Bonistein;prunetol;GeniVida;G2535;BIO-00;BIO300
- CBNumber:
- CB6163787
- Molecular Formula:
- C15H10O5
- Molecular Weight:
- 270.24
- MOL File:
- 446-72-0.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/7/29 17:07:33
| Melting point | 297-298 °C |
|---|---|
| Boiling point | 333.35°C (rough estimate) |
| Density | 1.2319 (rough estimate) |
| refractive index | 1.6000 (estimate) |
| storage temp. | -20°C |
| solubility | DMSO: soluble |
| form | powder |
| pka | 6.51±0.20(Predicted) |
| color | off-white |
| Water Solubility | insoluble |
| Merck | 14,4391 |
| BRN | 263823 |
| Stability | Light Sensitive |
| InChIKey | TZBJGXHYKVUXJN-UHFFFAOYSA-N |
| LogP | 3.114 (est) |
| CAS DataBase Reference | 446-72-0(CAS DataBase Reference) |
| EPA Substance Registry System | 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)- (446-72-0) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302 | |||||||||
| Precautionary statements | P264-P270-P301+P312-P501 | |||||||||
| Hazard Codes | Xi,Xn | |||||||||
| Risk Statements | 36/38-22 | |||||||||
| Safety Statements | 26-24/25-22 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | NR2392000 | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | IRRITANT | |||||||||
| HS Code | 29329990 | |||||||||
| NFPA 704 |
|
Genistein price More Price(21)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | G6776 | Genistein from Glycine max (soybean), ~98% (HPLC) | 446-72-0 | 5MG | ₹9320.33 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1859 | Genistein Pharmaceutical Secondary Standard; Certified Reference Material | 446-72-0 | 100MG | ₹15144.18 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | G6776 | Genistein from Glycine max (soybean), ~98% (HPLC) | 446-72-0 | 10MG | ₹15631.3 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | G6649 | Genistein synthetic, ≥98% (HPLC), powder | 446-72-0 | 5MG | ₹4784.65 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | G6649 | Genistein synthetic, ≥98% (HPLC), powder | 446-72-0 | 25MG | ₹15912.75 | 2022-06-14 | Buy |
Genistein Chemical Properties,Uses,Production
Chemical Properties
Yellow Crystalline Solid
Uses
Exhibits specific inhibitory activity against tyrosine kinases,including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell proliferation and induces tumor cell differentiation. Produces cell-cycle arrest and apoptosis in Jurat T-leukemia cells. However, it prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Genistein also inhibits topoisomerase II activity in vitro. Genistein has also been shown to inhibit the action of GABA on recombinant GABAA receptors 2. uv(max)ethanol: 262.5 nm (e= 138). moderately sol. in hot alcohol
Definition
ChEBI: 7-Hydroxyisoflavone with additional hydroxy groups at positions 5 and 4'. It is a phytoestrogenic isoflavone with antioxidant properties.
General Description
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards
Biological Activity
Phytoestrogen with a wide range of biological actions. Inhibits protein tyrosine kinases including epidermal growth factor receptor kinase. Also binds to PPAR γ and estrogen receptors and acts as an agonist at GPR30. Also available as part of the MAPK Cascade Inhibitor Tocriset™ .
Mechanism of action
Genistein, an isoflavone isolated from soybeans, exhibits anticarcinogenic and antioxidant properties. Particularly, genistein has been shown to inhibit production of IL-6 and MAPK. Modulation to these cellular events may help regulate and attenuate UVB-induced inflammatory damage to the skin. Moreover, genistein inhibits UV-induced oxidative DNA damage and blocks UV-induced expression of c-fos and c-jun proto-oncogenes.
Anticancer Research
It is an isoflavone and is obtained from a variety of plants like psoralea (Psoraleacorylifolia), kudzu (Pueraria lobata), faba beans (Vicia faba), and soybeans(Glycine max). It exhibits anticancer effect by inhibiting NF-κB and protein kinaseB (Akt) signaling pathways (Singh et al. 2016b). It blocks the proliferation of cancercells via the inhibition of cell growth enzymes and survival like tyrosine kinase andtopoisomerase II; hence it is used to treat leukemia. Genistein increases the growthrate of some estrogen receptors in breast cancer cells and the rate of proliferation of estrogen-dependent breast cancer by competitive binding to the estrogen-β receptors.It may be involved in JNK pathway in inducing activator protein-1(AP-1) activity(Wang et al. 2012; Dixon and Ferreira 2002).
Safety Profile
Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Purification Methods
Crystallise it from EtOH or aqueous EtOH. It has UV: max at 290nm (EtOH). The S(-)-enantiomer (natural form) has m 255-256o (from EtOH) and [] D 20 -28.0o (c 2, EtOH), [ ] D 20 -35.2o (c 1, pyridine).[Beilstein 18 H 503, 18 II 164, 18 III/IV 2630.] Genistein (4',5,7-trihydroxyisoflavone) [446-72-0]M 270.2 crystallises from 60% aqueous EtOH or water with m 297-298o and [] D 20 -28o (c 0.6, 20mM NaOH). [Beilstein 18/4 V 594.]For Naringin (naringenin 7-rhamnoglucoside) See “Carbohydrates” in Chapter 6.
Genistein Preparation Products And Raw materials
Raw materials
Preparation Products
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