Genistein
Genistein
CAS: 446-72-0
Molecular Formula: C15H10O5
Genistein - Names and Identifiers
| Name | Genistein |
| Synonyms | prunetol Genistein C.I. 75610 sophoricol AKOS NCG1-0029 4,5,7-Trihydroxyisoflavone 4',5,7-TRIHYDROXYISOFLAVONE 4',5,7-trihydroxyisoflavone 4',5,7-trihydroxy-isoflavon 5,7,4'-TRIHYDROXYISOFLAVONE 5,7-DIHYDROXY-3-(4-HYDROXY-PHENYL)-CHROMEN-4-ONE 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one 5,7-DIHYDROXY-3-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE |
| CAS | 446-72-0 |
| EINECS | 207-174-9 |
| InChI | InChI=1/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 |
| InChIKey | TZBJGXHYKVUXJN-UHFFFAOYSA-N |
Genistein - Physico-chemical Properties
| Molecular Formula | C15H10O5 |
| Molar Mass | 270.24 |
| Density | 1.2319 (rough estimate) |
| Melting Point | 297-298 °C |
| Boling Point | 333.35°C (rough estimate) |
| Flash Point | 217.1°C |
| Water Solubility | insoluble |
| Solubility | Soluble in commonly used organic solvents, almost insoluble in water, and yellow in dilute alkali. |
| Vapor Presure | 6E-13mmHg at 25°C |
| Appearance | Pale yellow dendritic needle crystal powder |
| Color | off-white |
| Merck | 14,4391 |
| BRN | 263823 |
| pKa | 6.51±0.20(Predicted) |
| Storage Condition | -20°C |
| Stability | Light Sensitive |
| Refractive Index | 1.6000 (estimate) |
| MDL | MFCD00016952 |
| Physical and Chemical Properties | Melting point 297-298°C water-soluble insoluble |
| Use | For anti-tumor, anti-fungal, hypolipidemic |
Genistein - Risk and Safety
| Risk Codes | R36/38 - Irritating to eyes and skin. R22 - Harmful if swallowed |
| Safety Description | 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 |
| TSCA | Yes |
| HS Code | 29329990 |
| Hazard Class | IRRITANT |
Genistein - Introduction
Open Data Unverified Data
- genistein is one of the main active factors in soybean isoflavones. It is the most effective functional component in Soybean isoflavone products and has a variety of physiological functions. Genistein is structurally similar to mammalian estrogen-estradiol and has a variety of physiological activities such as estrogenic activity because it has the active group of estrogen-diphenolic hydroxyl group.
- soybean isoflavones are a class of secondary metabolites formed in the growth of soybean. There are 12 kinds of naturally occurring isoflavones in soybean, which can be divided into 3 categories, namely, Daidzin groups, Genistin groups, daidzein glycosides (glycin groups), each type of free type (aglycone), glucoside type, acetyl glucoside type, malonyl glucoside type 4 forms. Isoflavone content in various soybeans is about 1200~4216 & micro;g/g, with isoflavone glucoside and malonyl isoflavone glucoside as the main form, A total of 95% to 98% of total isoflavones; And free isoflavones (aglycones) content is very low.
Last Update：2022-01-01 08:49:06
Genistein - Pharmacological action
Open Data Unverified Data
-
Genistein, also known as genistein, is a polyphenolic compound found in plants such as soybeans and red clover, with a molecular structure similar to 17 β-estradiol, with antioxidant and high affinity for estrogen receptor, can inhibit tyrosine protein kinase (PTK) and topoenzyme II activity, with the induction of programmed cell death, improve anti-cancer efficacy, inhibition of angiogenesis and other effects, it is a type of flavonoid (also known as isoflavone). Often found with isoflavones called daidzein, they are all called soy isoflavones. The human health benefits of these compounds have been extensively studied as a potential cancer chemopreventive agent with significant impact in the prevention of cancer and other diseases. Genistein is the main phytoestrogen in current research.
- Plant Source: legume dye Wood (plantain).
- Clinical Application: it can be used for female beauty care and prevention of blood diseases and cancer.
- genistein has a polyphenol hydroxyl structure, and the hydrogen atom on the phenolic hydroxyl group is easy to separate from the oxygen atom under the external action to form hydrogen ion and play a reducing effect, which is that genistein can resist oxidation, has a reductive structural basis. Therefore, such substances in food can fight superoxide anion free radicals, block the chain reaction of free radicals, and play an antioxidant role.
- genistein is not a hormone, but is called phytoestrogen because it can bind to estrogen receptors and exert a weak estrogenic effect. Since the activity of isoflavones is 1000/2 of that of estradiol, it competitively binds to estrogen receptor and shows a bidirectional regulation effect, which is much lower than the harmful effect of estradiol, and has a protective effect on hormone-related diseases, such as menopausal syndrome, osteoporosis, elevated blood lipids, etc.; For high estrogen levels, the performance of anti-estrogen activity, can prevent breast cancer, endometritis, it has the function of bidirectional balance regulation.
- genistein has the effect of lowering cholesterol and triglyceride in serum of rats with high blood lipid induced by trinitrotoluene WR1339, especially the latter.
Last Update：2022-01-01 08:49:06
Genistein - Safety Information
Open Data Unverified Data
mark of dangerous goods Xi
Hazard code 36/38
Safety instructions 26-24/25-22
WGK Germany 3
RTECS# NR2392000
HazardClass IRRITANT
Toxic Substance Data: 446-72-0(Hazardous Substances Data)
Last Update：2022-01-01 08:49:06
Genistein - Physical and chemical properties
Open Data Unverified Data
light yellow dendritic needle crystal powder. mp297 ℃-298 ℃; Soluble in commonly used organic solvents, almost insoluble in water, soluble in dilute alkali yellow.
Last Update：2022-01-01 08:49:05
Genistein - Related information
Open Data Unverified Data
- Many research reports and animal experiments show that soybean isoflavones have weak estrogenic activity, antioxidant activity, anti-hemolytic activity and antifungal activity, which can effectively prevent and inhibit leukemia, osteoporosis, colon cancer, lung cancer, gastric cancer, breast cancer and prostate cancer, women's climacteric syndrome and other diseases, especially for breast cancer and prostate cancer have a positive role in the prevention and treatment.
- studies have shown that genistein and Its aglycone are the most abundant components in soybean isoflavones. The aglycone form of Soybean isoflavone is more active than the glycoside form, especially the activity of genistein is higher. Genistein is one of the main active factors in soybean isoflavones. It is the most effective functional component in Soybean isoflavone products and has a variety of physiological functions.
- the chemical structure determines the chemical properties. Genistein is structurally similar to mammalian estrogen-estradiol and has a variety of physiological activities such as estrogenic activity because it has the active group of estrogen-diphenolic hydroxyl group.
- soybean isoflavones exist in various forms of glucoside. These glucosides have a strong physiological function only in the form of an aglycone formed by hydrolysis in vivo. Toru Izumi et al. studies have shown that in the human body, the absorption rate and the absorption amount of Soybean isoflavone aglycone are much larger than that of its glycoside form. The activity of genistein was higher. Genistein is a kind of Soybean isoflavone with various biological activities. It is a potent antioxidant, a potent inhibitor of the protein tyrosine-activating enzyme, a phytoestrogen. In recent years, more and more evidence shows that this natural ingredient has preventive and therapeutic effects on breast cancer, prostate cancer, postmenopausal syndrome, osteoporosis, and cardiovascular diseases.
Last Update：2022-01-01 08:49:07
Genistein - Selection method
Open Data Unverified Data
soy isoflavones brand, consumers are at a loss, choose soy isoflavones?
- choose from the dosage form of isoflavones, be careful or not to choose soft capsule products. Why? First, because the raw material of Soybean isoflavone is powder, water-soluble and fat-soluble are not good, so the choice of liquid solvent itself is not scientific; Second, Soft Capsule is used to protect easy oxidation, prone to deterioration of drugs or health care products, soy isoflavone stability is very good, not easy to oxidation and deterioration, so there is no need to take soft capsule packaging; Third, soft capsule packaging costs higher than hard capsules and tablets, therefore, the cost of soft capsules is high. It is not competitive, if the soft capsule products are sold very cheap, it is questionable; Fourth, the current market of Soybean isoflavone soft capsules are not transparent capsules. Or pink, or gray, etc., why opaque (similar to fish oil products), because transparent will expose the product defects. So it is not recommended that you buy soft capsules, and the content of the active ingredients of many Soft Capsule products is questionable. Soy isoflavones or hard capsules and tablets is better. If the gastrointestinal function is better, you can choose capsules and tablets, if the gastrointestinal function is not good, it is best to choose tablet products.
- Choose a brand or brand product: do not choose a particularly cheap product. A lot of small business fraud, product prices are very low, the quality of the product is difficult to guarantee; Also do not choose particularly expensive products, many products fake as foreign, Hong Kong and Macao brands, the price is very high, product quality is not necessarily guaranteed, because of quality problems, there is no way to claim.
- choice of production and operation of many years of products: production and operation of a long time, proved that the products of the enterprise through the market of the survival of the fittest, only high-quality products can survive for a long time. Products that have not been long-term selected by the market, the quality of the product is not reliable.
- select products with a clear soy isoflavone content on the product label: Many companies do not clearly indicate the active ingredient content on the label because the content is low. Soybean isoflavone active ingredient, take 50-100mg a day to have the effect, some products are made with soybean powder, the effective ingredient is insufficient, the effect is not good.
- choose products with anti-counterfeiting marks: because the products are selling well, there are fakes on the market, and it is easy to buy fakes without anti-counterfeiting measures.
- choose non-genetically modified, natural raw material extraction products: it is not recommended that you choose to import or sham import (domestic production of foreign trademarks) soy isoflavone products, because of the import of genetically modified soybean extraction, the false import of the product is the deception of the people. Some non-standard pharmaceutical companies also produce soy isoflavones, because they often use hormones, so in order to improve the product effect, some companies add hormones to the product.
- choose products produced by professional companies, do not choose small health care products, or labeled products.
soy isoflavones are very good women's health food, want consumers to be responsible for their own body. To view each other's production and quality procedures.
Last Update：2022-01-01 08:49:08
Genistein - Efficacy
Open Data Unverified Data
Prevention and improvement of osteoporosis
osteoporosis refers to the reduction of bone tissue, resulting in brittle and fragile bones, easy to fracture. Common in post-menopausal women and older men (due to hormonal changes or calcium and vitamin D deficiencies). The Incidence Rate of osteoporosis in middle-aged and elderly women is much higher than that in men. The main reason is the decline of estrogen level after the decline of ovarian function, the negative balance of bone metabolism and the decrease of bone mass. Isoflavones can bind to estrogen receptors on bone cells, reduce bone loss, increase the body's absorption of calcium and increase bone density.
Prevention of menopausal syndrome in women
- before and after menopause, due to the decrease of ovarian function and the decrease of estrogen level in the body, the functional adjustment of various organs and tissues is not adapted, and a series of diseases occur, and estrogen supplementation can achieve the purpose of prevention and treatment of such diseases.
- Women's menopause: hot flashes, sweating, chills, chest tightness, palpitations, shortness of breath, dizziness, blood pressure fluctuations, etc.; Emotional instability, irritability, irritability or depression, sleep Initiation and Maintenance Disorders, memory loss, thinking is not concentrated, comprehensive judgment decreased.
prevention of breast cancer
long-term use of estrogen alone can increase the incidence of breast cancer and endometrial cancer by 5 to 7 times. Soy isoflavones are similar in structure to estrogen, so they can bind to estrogen receptors on the cell surface and activate other anti-cancer mechanisms, reducing the risk of endometrial and breast cancer in women with high levels of estrogen.
cancer prevention
- soy products contain 5 known anti-cancer factors, one of which is phytoestrogen (isoflavone), an anti-cancer factor specific to soy foods. The scientists concluded that the antioxidant properties of genistein and its ability to prevent hyperplasia are the main reasons for its anti-cancer effect. Soy isoflavones have obvious therapeutic effect on breast cancer, colon cancer, lung cancer, prostate cancer, skin cancer and leukemia. Soy isoflavones can also prevent ovarian cancer, colon cancer, gastric cancer and prostate cancer.
- a large number of studies have found that soy isoflavones can make cancer cells into cells with normal function, at the same time, can also inhibit the structure of bad lumps, prevent the proliferation of lumps and cancer cells.
prevention of cardiovascular disease
heart disease is also a disease related to estrogen. As a phytoestrogen, Soybean isoflavone lowers blood lipid and prevents heart disease by the following mechanism: estrogen-like effect promotes thyroxine secretion, promotes bile excretion. The ability to lower low density lipoprotein (LDL) cholesterol without lowering high density lipoprotein (HDL) cholesterol in lowering cholesterol is well documented. It is very important that isoflavones, as a characteristic of flavonoids, have a biological antioxidant effect. Because the oxidation of low density lipoprotein (LDL) cholesterol is a key factor in the atherosclerotic process. Women receiving 80 mg of genistein daily increase arterial elasticity by about 26%.
prevention of Alzheimer's disease
Alzheimer's disease is by far the most common form of dementia and is more common in women. In recent years, studies have shown that the human brain also belongs to the target tissue of estrogen, and the hippocampal synaptosomes with memory function in the brain contain estrogen receptors. The medical profession has confirmed that estrogen levels are closely related to senile dementia, both soy isoflavones and real estrogen are good for the brain.
beauty, anti-aging role
- the estrogen-like effect of soy isoflavones can make women's skin smooth, delicate, tender, elastic, and radiant. Women through the replacement of estrogen to activate the fat tissue in the breast, so that free fat is attracted to the breast, so as to achieve the effect of breast.
- research shows that: modern women in the early menopause phenomenon, long-term supplementation of soy isoflavones can make the body estrogen to maintain normal levels, delay menopause, to achieve the effect of anti-aging.
improve menstrual discomfort
menstrual discomfort is generally related to the imbalance of estrogen secretion. Long-term supplementation of Soybean isoflavone can maintain the normal level of estrogen in the body and achieve the purpose of improving menstrual discomfort.
improve the quality of sexual life
The estrogen-like effect of soy isoflavones can increase the maturation of vaginal epithelial cells and the elasticity of vaginal muscles, thus improving the quality of sexual life.
lower cholesterol
cardiovascular disease (CHD) is a multifactorial disease, in which cholesterol (Ch) plays an important role. A large-scale study of 5000 people was conducted in Japan, the results of which show that soy isoflavones have a lowering effect on the formation of thrombus of cholesterol Ch. A dose-response relationship for isoflavones was shown in a British study of young women, with more than 45 mg of isoflavones per day for 30 consecutive days lowering total Ch and LDL-Ch levels by 10%, while 23 mg of isoflavones had no effect.
regulation of blood lipid to prevent cardiovascular disease
soy isoflavones can reduce the susceptibility of the body to serum LDL oxidation. After the serum LDL lipoprotein is oxidized, the phagocytosis of macrophages in the human body is activated, and the foam cells are developed in the arterial wall, and the atherosclerotic plaque is formed. Soybean isoflavone not only has its own antioxidant effect, but also can induce the increase of antioxidant enzyme activity, improve the antioxidant activity of serum LDL, prevent the formation of atherosclerotic plaque in arterial wall, and prevent vascular atherosclerosis. At the same time, increase the compliance of arterial blood vessels and dilate blood vessels. Soy isoflavones also inhibit the process of atherosclerosis by affecting tyrosine kinases, including foam cells, fat-like striae, hyperplasia, fibrous plaque infiltration, rupture and ulceration, and maintain the smooth flow of heart arteries, prevention of the occurrence of cardiovascular diseases.
Last Update：2022-01-01 08:49:10
Genistein - Reference Information
| Plant source: | Soybean |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| properties | genistein is light yellow crystalline powder; The air is slight and the taste is bitter. |
| Use | Genistein has the properties of estrogen and anti-estrogen, has an antioxidant effect, can inhibit the activity of tyrosine protein kinase (PTK), and can inhibit the activity of topological xenoenzyme Ⅱ. It has the effects of inducing programmed cell death, improving anti-cancer efficacy, and inhibiting angiogenesis. It is a potential cancer chemoprevention agent, its anti-cancer effect and mechanism have broad application prospects. Anti-tumor, antifungal, blood-lowering Buddha, estrogen spell activity. for anti-tumor, anti-fungal, lower blood lipid 1, with estrogen and anti-estrogen properties 2, in vivo can inhibit colon cancer, breast cancer, skin cancer, prostate cancer, etc. 3, has inhibitory effect on a variety of tumor cell lines 4, has antioxidant effect 5, can inhibit the activity of tyrosine protein kinase (PTK) 6, can inhibit the activity of topoheterocytase Ⅱ 7, can prevent postmenopausal osteoporosis 8, has the effects of inducing programmed cell death, improving anti-cancer efficacy, inhibiting angiogenesis, etc, it is a potential cancer chemoprevention agent, and its anti-cancer effect and mechanism have a wide range of applications. tyrosine protein kinase (PTK) inhibitors, competitive inhibitors of ATP in other protein kinase reactions, induce programmed cell death, improve anti-cancer efficacy, inhibit angiogenesis, etc. |
| Pharmacological effects | Genistein, also known as genistein, is a polyphenolic compound that can be found in plants such as soybeans and red clover. Its molecular structure is similar to 17 β-estradiol. It has antioxidant properties and high affinity for estrogen receptors. It can inhibit the activity of tyrosine protein kinase (PTK) and topoheterooxyase II, it has the effects of inducing programmed cell death, improving anti-cancer efficacy, and inhibiting angiogenesis. It is a type of flavonoids (also called isoflavones). Often found with isoflavones called daidzein, they are all called soy isoflavones. The health benefits of these compounds have been extensively studied and are a potential cancer chemoprevention agent with a significant impact on the prevention of cancer and other diseases. Genistein is the main phytoestrogens currently studied. Plant source: Leguminosae dye wood (gorse). clinical application: it can be used for women's beauty care and prevention of blood diseases and cancer. Genistein has a polyphenol hydroxyl structure. The hydrogen atom on the phenolic hydroxyl group is easy to separate from the oxygen atom under the external action to form hydrogen ions and exert a reducing effect. This is the antioxidant and reducing effect of genistein. Structural basis. Therefore, such substances in food can resist superoxide anion free radicals, block the chain reaction of free radicals, and exert antioxidant effects. Genistein is not a hormone, but because it can bind to estrogen receptors to exert a weak estrogen effect, it is called phytoestrogen. Since the activity of isoflavones is 1/1000 of estradiol, they competitively bind to estrogen receptors with estradiol, showing two-way regulation, and the estrogen effect produced is much lower than the harmful effect of estradiol. It has a protective effect on hormone-related diseases, such as menopausal syndrome, osteoporosis, elevated blood lipids, etc.; for those with high estrogen levels, it exhibits anti-estrogen activity, which can prevent breast cancer and endometritis, and has a two-way regulation of balance function. genistein on trinitrotoluene WR1339 induced hyperlipidemia in rats, has the effect of reducing the serum cholesterol and triglyceride, especially for the latter. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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