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Genistein

CAS：446-72-0
MW:270.24
MF：C15H10O5

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. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Genistein

1.2 Synonyms: 4',5,7-TRIHYDROXYISOFLAVONE; 4’,5,7-trihydroxy-isoflavon; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-; 5,7,4'-TRIHYDROXYISOFLAVONE; 5,7-DIHYDROXY-3-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE; 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one; 5,7-DIHYDROXY-3-(4-HYDROXY-PHENYL)-CHROMEN-4-ONE; 5-18-04-00594; 5-18-04-00594 (Beilstein Handbook Reference); AKOS NCG1-0029; Bonistein; EINECS 207-174-9; Genestein; genisteol; GeniVida; GLYCITEN; MFCD00016952; NPI 031L; prunetol; sophoricol;

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1.3 CAS No.: 446-72-0

1.4 CID: 5280961

1.5 EINECS: 207-174-9

1.6 Molecular Formula: C15H10O5

1.7 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

1.8 InChkey: TZBJGXHYKVUXJN-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O

1.10 Isomers Smiles: C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O

2. Properties

2.1 Solubility: DMSO: soluble

2.2 Λmax: 262(MeOH)nm

2.3 Appearance: off-white powder

2.4 Storage: Store at -20°C.

2.5 Color/Form: off-white

2.6 Physical: Solid

2.7 pKa: 6.51±0.20(Predicted)

2.8 Water Solubility: H2O: insoluble ;DMSO: soluble

2.9 Spectral Properties: UV max: 262.5 (epsilon 138)

2.10 Stability: Light Sensitive

2.11 StorageTemp: ?20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: 7-Hydroxyisoflavone with additional hydroxy groups at positions 5 and 4'. It is a phytoestrogenic isoflavone with antioxidant properties.

3.2 Description: Genistein, a soy isoflavone, is a multiple tyrosine kinases inhibitor which acts as a chemotherapeutic agent against different types of cancer, mainly by altering apoptosis, the cell cycle, and angiogenesis and inhibiting metastasis.

3.3 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 88 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 6 of 88 companies. For more detailed information, please visit ECHA C&L website

Of the 4 notification(s) provided by 82 of 88 companies with hazard statement code(s):

H302 (96.34%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (58.54%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (58.54%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (58.54%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H400 (56.1%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410 (56.1%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501

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3.4 Methods of Manufacturing: Preparation: from the glucoside by hydrolysis with emulsin

3.5 Usage: It has anti-tumor, anti-fungal, blood lipid-lowering and can fight against estrogen activity.

4. Safety and Handling

4.1 Octanol/Water Partition Coefficient: log Kow = 2.84 (est)

4.2 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

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4.3 Safety Profile: Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

4.4 Formulations/Preparations: Genistein is available in a few different isoflavone formulas. A standard soy isoflavone formula contains genistein mainly in the form of genistin, as well as daidzin and glycitin. The percentages of the various isoflavones present in this soy formula reflect the percentages of these substances as found in soybeans and are: genistin, about 50%; daidzin, about 38%; and glycitin, about 12%. A 50 mg dose of soy isoflavones?a typical daily dose?provides 25 mg of genistin, 19 mg of daidzin and about 6 mg of glycitin. Usually, 40% of the formula is comprised of soy isoflavones. Therefore, to get a dose of 50 mg of soy isoflavones, one needs 125 mg of the soy preparation. Smaller amounts of genistein as the aglycone are available in some red clover preparations.

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4.5 Report: ? Genistein (CAS NO.446-72-0) is reported in EPA TSCA Inventory.

4.6 Safety: Hazard Codes:?Xi
Risk Statements: 36/38
R36/38:Irritating to eyes and skin.
Safety Statements: 26-24/25-22
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S24/25:Avoid contact with skin and eyes.?
S22:Do not breathe dust.
WGK Germany: 3
RTECS: NR2392000

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4.7 Specification: ?Biological effects of Genistein (CAS NO.446-72-0) are some isoflavones act as antioxidants to counteract damaging effects of free radicals in tissues; Genistein protects against pro-inflammatory factor-induced vascular endothelial barrier dysfunction and inhibits leukocyte-endothelium interaction, thereby modulating vascular inflammation, a major event in the pathogenesis of atherosclerosis and it?makes some cells more sensitive to radio-therapy.

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4.8 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD	intraperitoneal	> 500mg/kg (500mg/kg)	?	Journal of Antibiotics. Vol. 39, Pg. 606, 1986.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P391 Collect spillage.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

446-72-0Total: 36 Synthesis Route

529-59-9 147 Suppliers

446-72-0 481 Suppliers

491-80-5 154 Suppliers

446-72-0 481 Suppliers

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8. Precursor and Product

precursor:

4693-91-8

156-38-7

104-47-2

491-80-5

480-41-1

152-95-4

529-59-9

108-73-6

product:

156-38-7

13539-26-9

51225-30-0

470666-97-8

152-95-4

480-23-9

15485-65-1

13539-27-0

108-73-6

552-59-0

187960-08-3

9. Computed Properties

Molecular Weight：270.24g/mol
Molecular Formula：C₁₅H₁₀O₅
Compound Is Canonicalized：True
Exact Mass：2.7
XLogP3-AA：270.05282342
Monoisotopic Mass：270.05282342
Complexity：411
Rotatable Bond Count：1
Hydrogen Bond Donor Count：3
Hydrogen Bond Acceptor Count：5
Topological Polar Surface Area：87
Heavy Atom Count：：20
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBwOAAAAAAAAAAAAAAAAAAAAAAAAAAwYIAAAAAAAACBQAAAGgAACAAADASgmAIwBoAABgCIAqBSAAACCAAkIAAIiAEGCMgMJzaGNRqAcWAl4BUIuYeI7PzOIAAACAAIAABAAAAQABAAAAAAAAAAAA==

10.Other Information

Merck: 14,4391

BRN: 263823

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.

View all

Pharmacological effects: Genistein is a kind of polyphenols compound which can be found in soy and red clover and other plants with its molecular structure being similar to 17β-estradiol and having antioxidant activity and high affinity towards estrogen receptor. It can inhibit the activity of protein tyrosine kinase (PTK) and topoisomerase enzyme activity II with capability of inducing programmed cell death and improve the efficacy of anti-cancer drug as well as inhibit angiogenesis, and so on. It is one type of flavonoids (also called isoflavones) and is often found together with isoflavones called the isoflavones. They are all called soy isoflavones. Those benefits of these kinds of compounds on human health have been studied extensively and it is a promising cancer chemopreventive agent with significant impact on preventing cancer and other diseases. Genistein is the major phytoestrogens in the present study.
Plant Source: legume Genista (broom).
Clinical Applications: it can be used for female beauty care and prevention of blood diseases and cancer.
Genistein contains polyphenol structure with the hydrogen atoms in the phenolic hydroxyl group being prone to dissociate from external oxygen atom from the external interaction, leading to the formation of hydrogen ions to play reduction effect. This is the structure basis for the capability of the genistein of anti-oxidative and reductive. So those substances in food can fight against superoxide anion radicals, blocking the chain reaction of free radicals and play a role in anti-oxidation.
Genistein is not a hormone, but because it can bind to estrogen receptors and plays a weak estrogenic effect, it is called phytoestrogens. Because the activity of isoflavones is only 1/1000 of the estradiol which can competitively bind with estrogen receptors, exhibiting two-way adjustment with the resulting estrogenic effects of much lower harmful effects than estradiol and further with protective effect on then hormone related diseases such as menopause, osteoporosis, elevated blood lipids, etc; for patients of high levels of estrogen, it exhibits anti-estrogenic activity and can prevent breast cancer, endometriosis with two-way balance adjustment function.
Genistein, for the rat high cholesterol induced by TNT (trinitrotoluene) WR1339, has effect of lowering serum cholesterol and triglycerides with the effect on the later one being particularly significant.
This information is edited by Xiongfeng Dai from .

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Uses: It has anti-tumor, anti-fungal, blood lipid-lowering and can fight against estrogen activity.

Mechanism of action: Genistein may inhibit cancer cell growth by blocking enzymes required for cell growth. Genistein may decrease cardiovascular risk in postmenopausal women by interacting with the nuclear estrogen receptors to alter the transcription of cell specific genes. In randomized clinical trials, genistein was seen to increase the ratio of nitric oxide to endothelin and improved flow-mediated endothelium dependent vasodilation in healthy postmenopausal women. In addition, genistein may have beneficial effects on glucose metabolism by inhibiting islet tyrosine kinase activity as well as insulin release dependent on glucose and sulfonylurea.
References
https://www.drugbank.ca/drugs/DB01645

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Health Benefits: Estrogenic effect
The estrogenic activity of genistein has been confirmed in many studies. Of all the isoflavones, genistein has the strongest estrogenic activity. The estrogenic effect of genistein may explain its protective action against osteoporosis and its possible effect on body weight reductions. Genistein is also used to ease menopause symptoms, such as hot flushes.
Antioxidant
Genistein is a strong antioxidant. Genistein removes damaging free radicals and reduces lipid peroxidation. Genistein increases the activity of other antioxidant enzymes such as glutathione peroxidase, superoxide dismutase and glutathione reductase. Studies have shown that genistein can also influence the growth of cells which are not hormone-dependent.
Anticancer
Genistein seems to reduce the risk for some hormone related cancers, principally breast cancer and prostate cancer. Epidemiological studies show that consumption of isoflavones may protect against breast and prostate cancer. High dietary intake of soy products China and Japan are linked with low incidence of these cancers. There are lots of theories to explain the anti-cancer action of genistein: inhibition of angiogenesis, inhibition of tyrosine kinases, antioxidant property, and anti-estrogen action (it is known that estrogen increases risk for certain cancers). Genistein binds with estrogen receptors, preventing the estrogen from binding and initiating cancer growth.

Heart health
Many in-vitro tests have demonstrated that genistein inhibits cellular cholesterol synthesis and cholesterol esterification. Genistein also reduces fatty acid oxidation and exerts lipid lowering effect. Only oxidized LDL cholesterol is absorbed by the arterial cells and prevention of this oxidation will reduce the risk for arteriosclerosis. Gensistein prevents the formation of hearth attacks and strokes by acting as anticlotting agent.
References
http://www.phytochemicals.info/phytochemicals/genistein.php

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Chemical Properties: Yellow Crystalline Solid

Uses: 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.

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

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Uses: cytotoxic inhibitor of tyrosine kinase and topoisomerase II kinase

Definition: ChEBI: 7-Hydroxyisoflavone with additional hydroxy groups at positions 5 and 4'. It is a phytoestrogenic isoflavone with antioxidant properties.

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? .

Safety Profile: Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Usage: 4',5,7-Trihydroxyisoflavone is used to inhibitor of tyrosine protein kinase. Genistein inhibits EGF-stimulated phosphorylation in cultured cells. Also used to explore signal transduction pathways.

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12. Related Questions

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