Genistein

Base Information

• Chemical Name: Genistein
• CAS No.: 446-72-0
• Molecular Formula: C15H10O5
• Molecular Weight: 270.241
• Hs Code.: 29329990
• Mol file: 446-72-0.mol

Synonyms:4H-1-Benzopyran-4-one, 5, 7-dihydroxy-3- (4-hydroxyphenyl)-;5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one;5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one;Prunetol;Isoflavone, 4,5,7-trihydroxy-;4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-;SIPI 807-1;5,7-Dihydroxy-3-(4-hydroxyphenyl)-4-benzopyrone;5-18-04-00594 (Beilstein Handbook Reference);C.I. 75610;NPI 031L;4,5,7-Trihydroxyisoflavone;4',5,7-trihydroxyisoflavone;4,5, 7-Trihydroxyisoflavone;Genisteol;Baichanin A;Differenol A;4H-1-Benzopyran-4-one,5,7-dihydroxy-3- (4-hydroxyphenyl)-;Genisterin;Sophoricol;5,7,4-Trihydroxyisoflavone;Genistein 4,5,7-Trihydroxyisoflavone;

Chemical Property of Genistein

Chemical Property:

• Appearance/Colour: Yellow crystalline solid
• Vapor Pressure: 6E-13mmHg at 25°C
• Melting Point: 297-298 °C
• Refractive Index: 1.732
• Boiling Point: 555.5 °C at 760 mmHg
• PKA: 6.51±0.20(Predicted)
• Flash Point: 217.1 °C
• PSA: 90.90000
• Density: 1.548 g/cm³
• LogP: 2.57680
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble
• Water Solubility.: insoluble

Purity/Quality:

99%, ^*data from raw suppliers

Genistein ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/38-22
• Safety Statements: 26-24/25-22

MSDS Files:

SDS file from LookChem

Useful:

• description: Genistein is one of the most abundant isoflavones in soy and is one of several known isoflavones. Isoflavones compounds, such as genistein and daidzein, are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Because of its similar structure to that of human estrogen it is also called a phytoestrogen. Genistein is a natural bioactive compound derived from legumes and has drawn because of its potentially beneficial effects on some human degenerative diseases. It has a weak estrogenic effect and is a well-known non-specific tyrosine kinase inhibitor at pharmacological doses. Genistein is a soy-derived isoflavone and phytoestrogen with antineoplastic activity. Genistein binds to and inhibits protein-tyrosine kinase, thereby disrupting signal transduction and inducing cell differentiation. This agent also inhibits topoisomerase-II, leading to DNA fragmentation and apoptosis, and induces G2/M cell cycle arrest. Genistein exhibits antioxidant, antiangiogenic, and immunosuppressive activities. In adult animals, dietary genistein has chemopreventive effects on breast, prostate, and other endocrine-dependent tumors.
• Uses: It has anti-tumor, anti-fungal, blood lipid-lowering and can fight against estrogen activity. genistein is an isoflavone commonly found in soy. It has demonstrated uV-protection properties through anti-oxidant activity. Studies indicate genistein can promote collagen synthesis, making it applicable in anti-aging cosmetics. 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 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. cytotoxic inhibitor of tyrosine kinase and topoisomerase II kinase
• Description: Genistein (446-72-0) is a naturally occurring flavonoid with a wide range of biological actions. Inhibits protein tyrosine kinases including epidermal growth factor receptor kinase.1,2?Phytoestrogen3?and agonist at GPR304. Displays cancer chemopreventive activity.5

Technology Process of Genistein

There total 68 articles about Genistein which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

genistin (529-59-9) → 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0)

Guidance literature:

β-glucosidase, derived from Aspergillus niger; In methanol; at 55 ℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;

Reference yield: 95.0%

sulfur trioxide N,N-dimethylformamide complex → 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0)

Guidance literature:

2,4,4',6-tetrahydroxydeoxybenzoin; With sodium carbonate; In N,N-dimethyl-formamide; at 25 ℃; for 3h;

sulfur trioxide N,N-dimethylformamide complex; In N,N-dimethyl-formamide; at 0 - 80 ℃; for 18.5h;

With sulfuric acid; water; In N,N-dimethyl-formamide; for 0.666667h; Product distribution / selectivity;

Reference yield: 94.8%

2,4,4',6-tetrahydroxydeoxybenzoin (15485-65-1) + sodium formate (141-53-7) → 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0)

Guidance literature:

2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate; With propionyl chloride; In acetone; at 21 - 32 ℃; for 1h;

With triethylamine; In acetone; at 20 - 32 ℃; for 2.5h;

With sulfuric acid; water; In acetone; at 20 ℃; for 16h; Product distribution / selectivity;

upstream raw materials:

5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on

5,7-dihydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromene-2-carboxylic acid

1,3,5-Triazine

2,4,4',6-tetrahydroxydeoxybenzoin

Downstream raw materials:

4-(7-acetoxy-5-hydroxy-4-oxo-4H-chromen-3-yl)phenyl acetate

7-(2-bromoethoxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

7-(3-bromopropoxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

4',5,7-tri(3-bromopropoxy)isoflavone

Refernces

• 1、 Hazato,Naganawa,Kumagai,Aoyagi,Umezawa. "β-Galactosidase-inhibiting new isoflavonoids produced by actinomycetes". . p. 217 - 222. Retrieved 1979.
• 2、 Laupattarakasem, Pisamai,Houghton, Peter J.,Hoult, J. Robin S.. "Anti-inflammatory isoflavonoids from the stems of Derris scandens". . p. 496 - 501. Retrieved 2004.
• 3、 Wang, Daijie,Khan, Muhammad Shafiq,Cui, Li,Song, Xiangyun,Zhu, Heng,Ma, Tianyu,Li, Xiaoyu,Sun, Rong. "A novel method for the highly efficient biotransformation of genistein from genistin using a high-speed counter-current chromatography bioreactor". . p. 4892 - 4899. Retrieved 2019.
• 4、 Djouossi, Marie Geneviève,Mabou, Florence Déclaire,Foning Tebou, Perrin Lanversin,Ngnokam, David,Tapondjou, Leon A.,Harakat, Dominique,Voutquenne-Nazabadioko, Laurence. "Chevalierinoside B and C: Two new isoflavonoid glycosides from the stem bark of Antidesma laciniatum Muell. Arg (syn. Antidesma chevalieri Beille)". . p. 149 - 152. Retrieved 2014.
• 5、 Do, Ji Min,Gee, Min Sung,Inn, Kyung-Soo,Kim, Jong-Ho,Kim, Nam Kwon,Kim, Nam-Jung,Lee, Hyun Woo,Lee, Jong Kil,Seo, Min-Duk,Seong, Ji Hye,Son, Seung Hwan,Yoo, Hyung-Seok,Yoo, Ji-Na. "Identification of ortho catechol-containing isoflavone as a privileged scaffold that directly prevents the aggregation of both amyloid β plaques and tau-mediated neurofibrillary tangles and its in vivo evaluation". . . Retrieved 2021/07/01.
• 6、 -. "Cytosine N-isoflavone compound as well as preparation method and application thereof". Paragraph 0029; 0037-0038. . Retrieved 2019/10/02.