Genistein
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| Category | Antibiotics |
| Catalog number | BBF-01840 |
| CAS | 446-72-0 |
| Molecular Weight | 270.24 |
| Molecular Formula | C15H10O5 |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-01840 | 5 g | $297 | In stock |
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Add to cartDescription
Genistein, a phytoestrogen found in soy products, is a highly specific inhibitor of protein tyrosine kinase (PTK) which blocks the mitogenic effect mediated by EGF on NIH-3T3 cells with IC50 of 12μM or by insulin with IC50 of 19 μM. Genistein is developed to be an antitumor agent. Genistein has antioxidant effect, it can be used in cosmetics material. It is a plant polyphenol that can inhibit tyrosinase, block melanin synthesis, reduce skin pigment intensity, absorb UV, prevent photoaging, reduce sun damage and age spot formation, and whiten and lighten spots. It also has the anti-glycation and antibacterial effect, can effectively improve skin tone and skin texture, prevent the generation of age spots, remove red bloodlines, and improve skin blood microcirculation.
Specification
| Synonyms | 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Baichanin A; Bonistein; 4',5,7-Trihydroxyisoflavone; GeniVida; Genisteol; NSC 36586; Prunetol; Sophoricol; Differenol A |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one |
| Canonical SMILES | C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O |
| InChI | InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H |
| InChI Key | TZBJGXHYKVUXJN-UHFFFAOYSA-N |
Properties
| Appearance | Pale Yellow to Light Beige Solid |
| Application | antitumor agent |
| Boiling Point | 555.5±50.0°C at 760 mmHg |
| Melting Point | 295-300°C |
| Flash Point | 217.1ºC |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in DMSO (Slightly), Methanol (Slightly) |
| LogP | 2.57680 |
Reference Reading
1.The synergy effect of daidzein and genistein isolated from Butea superba Roxb. on the reproductive system of male mice.
Eumkeb G1, Tanphonkrang S2, Sirichaiwetchakoon K1, Hengpratom T1, Naknarong W1. Nat Prod Res. 2016 Apr 29:1-4. [Epub ahead of print]
Butea superba Roxb. (BS) has been used in Thai men as an aphrodisiac, and prevent erectile dysfunction. Nevertheless, the active ingredients, dosages, have not been cleared. Hence, this study was to investigate the effect of compounds from the BS on the reproductive parameters of male mice. The results revealed that BS was extracted to afford biochanin A and genistein, which were first reported on BS, and daidzein. The mice were treated by daidzein and genistein alone and in combination. The results showed that the sperm number and motility, cholesterol and testosterone level of all isoflavones-treated groups were significantly higher than controls (p < 0.01). Obviously, daidzein plus genistein exhibited a synergistic effect, which is also the first report, and resulted in significantly displayed higher levels of these parameters compared to others. So, the synergistic activity of these isoflavones may be useful in improving libido, erectile capacity and assist infertility of poor spermatozoa in men.
2.Improve ethanol tolerance of β-glucosidase Bgl1A by semi-rational engineering for the hydrolysis of soybean isoflavone glycosides.
Fang W1, Yang Y2, Zhang X1, Yin Q1, Zhang X1, Wang X3, Fang Z4, Xiao Y5. J Biotechnol. 2016 Apr 12. pii: S0168-1656(16)30202-4. doi: 10.1016/j.jbiotec.2016.04.022. [Epub ahead of print]
A β-glucosidase Bgl1A variant (A24S/F297Y) with improved ethanol tolerance was obtained by semi-rational engineering. At 30-40°C, IC50 values (the amount required for inhibiting 50% enzyme activity) of the variant for ethanol were 17%-30% (v/v), 1.4- to 2.4-fold of Bgl1A. When incubating in 15% (v/v) ethanol at 30°C, the half-life of A24S/F297Y was 13min; whereas Bgl1A lost all enzyme activity within 5min. A24S/F297Y was more stable at pH 7.5 than at pH 6.5, and more than 50% of the original activity remained after incubation at 30°C for 10h. At 35°C and pH 7.5, the half-life of A24S/F297Y was 80min, 4.3 times longer than that of Bgl1A. When converting isoflavone glycosides to aglycones using A24S/F297Y as catalyst, the hydrolysis rates were 99% for daidzin and 98% for genistin. The concentrations of daidzein and genistein rapidly increased by 7.02mM and 4.35mM within 10min, respectively. These results showed that A24S/F297Y was a promising candidate for the enzymatic hydrolysis of soybean isoflavone glycosides.
3.Trichostatin A potentiates genistein-induced apoptosis and reverses EMT in HEp2 cells.
Du R1, Liu Z2, Hou X3, Fu G3, An N3, Wang L1. Mol Med Rep. 2016 Apr 28. doi: 10.3892/mmr.2016.5204. [Epub ahead of print]
Genistein and trichostatin A (TSA) are two chemotherapeutic compounds with antitumor effects in different types of cancer cell. However, the effects of genistein and TSA on the HEp‑2 laryngeal cancer cell line remain to be fully elucidated. In the present study, it was found that genistein and TSA inhibited cell growth and cell migration, and promoted apoptosis in the HEp‑2 laryngeal cancer cell line. The HEp‑2 cells were treated with genistein, TSA or the two compounds in combination. Cell proliferation and apoptosis were measured using an MTT assay, Annexin V/propidium iodide staining and a TUNEL assay. Cell invasion was determined using a Matrigel‑based Transwell assay. Western blotting was used to examine the activation of the Akt pathway and the expression levels of pro‑or anti‑apoptotic proteins. Treatment with either genistein or TSA alone mildly inhibited cell viability, growth and invasion, and induced the apoptosis of the laryngeal cancer cells, whereas more marked effects were observed in the cells treated with the combination of the two compounds.
4.Genistein decreases basal hepatic cytochrome P450 1A1 protein expression and activity in Swiss Webster mice.
Froyen EB1, Steinberg FM2. Nutr Res. 2016 May;36(5):430-9. doi: 10.1016/j.nutres.2016.01.001. Epub 2016 Jan 8.
Soy consumption has been associated with risk reduction for chronic diseases such as cancer. One proposed mechanism for cancer prevention by soy is through decreasing cytochrome P450 1A1 (Cyp1a1) activity. However, it is not known with certainty which soy components modulate Cyp1a1, or the characteristics or mechanisms involved in the responses after short-term (<20 days) dietary treatment without concomitant carcinogen-mediated induction. Therefore, the objective was to test the hypothesis that physiologic concentrations of dietary genistein and/or daidzein will decrease basal hepatic Cyp1a1 protein expression and activity in male and female Swiss Webster mice via inhibiting the bindings of aryl hydrocarbon receptor (AhR)-AhR nuclear translocator (ARNT) and estrogen receptor-α to the Cyp1a1 promoter region xenobiotic response element. The mice were fed the AIN-93G diet supplemented with 1500 mg/kg of genistein or daidzein for up to 1 week.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
