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Genistein(CAS No. 446-72-0)

Genistein C15H10O5 (cas 446-72-0) Molecular Structure

446-72-0 Structure

Identification and Related Records

【Name】
Genistein
【CAS Registry number】
446-72-0
【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
【EINECS(EC#)】
207-174-9
【Molecular Formula】
C15H10O5 (Products with the same molecular formula)
【Molecular Weight】
270.24
【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
【Canonical SMILES】
C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O
【MOL File】
446-72-0.mol

Chemical and Physical Properties

【Appearance】
Yellow Crystalline Solid
【Density】
1.548 g/cm3
【Melting Point】
297-298℃
【Boiling Point】
555.5 °C at 760 mmHg
【Vapour】
6E-13mmHg at 25°C
【Refractive Index】
1.732
【Flash Point】
217.1 °C
【Water】
insoluble
【Solubilities】
insoluble
【Color/Form】
off-white
【Stability】
No data.
【Storage temp】
?20°C
【Spectral properties】
UV max: 262.5 (epsilon 138)
【Computed Properties】
Molecular Weight:270.2369 [g/mol]
Molecular Formula:C15H10O5
XLogP3-AA:2.7
H-Bond Donor:3
H-Bond Acceptor:5
Rotatable Bond Count:1
Tautomer Count:24
Exact Mass:270.052823
MonoIsotopic Mass:270.052823
Topological Polar Surface Area:87
Heavy Atom Count:20
Formal Charge:0
Complexity:411
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:3
Feature 3D Ring Count:3
Effective Rotor Count:1
Conformer Sampling RMSD:0.6
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xi: Irritant;
【Risk Statements】
R36/38
【Safety Statements 】
S24/25
【HazardClass】
IRRITANT
【Safety】

Hazard Codes:?IrritantXi
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

【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.
【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.

【Octanol/Water Partition Coefficient】
log Kow = 2.84 (est)
【Report】

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

【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Preparation: from the glucoside by hydrolysis with emulsin
【Usage】

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

Biomedical Effects and Toxicity

【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? .
【Pharmacological Action】
- Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.
- PLANT EXTRACTS and compounds, primarily ISOFLAVONES, that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.
- Agents that inhibit PROTEIN KINASES.
【Therapeutic Uses】
/EXPTL/ Genistein is speculated to provide beneficial effects on cardiovascular and bone health and to alleviate menopausal symptoms; studies examining such endpoints have been limited in number, provided inconsistent findings, or evaluated soy product consumption instead of exposure to genistein alone.
/EXPTL/ Interest in ... /genistein/ is concentrated in particular on its therapeutic role in menopause. This paper is a review of the main studies published to date on the efficacy of phytoestrogens in reducing the symptoms of menopause. A diet rich in isoflavones is associated with a reduced incidence of vasomotor episodes; the average supplement of genistein is approximately 50 mg/day. After supplementing the diet with phytoestrogens, studies show a reduction in total cholesterol and LDL fraction. This is accompanied by an increase in BMD (Bone mineral density) after taking 90 mg of isoflavones for 6 months. Isoflavones may reduce the risk of developing breast cancer. The data examined confirm the excellent clinical efficacy of supplementing the diet with soy extracts, particularly genistein which is indicated to alleviate both the short-term symptoms of menopause and the long-term effects, although the latter finding requires further subsantiation. [Arena S et al; Minerva Ginecol 54 (1): 53-7 (2002)]
【Biomedical Effects and Toxicity】
... Genistein is rapidly absorbed in humans following oral intake. Before absorption into the systemic circulation, most genistein is conjugated with glucuronic acid and excreted in the bile to undergo enterohepatic circulation ... . Therefore, genistein bioavailability is very limited. Times to obtain maximum plasma concentrations were reported at 1 to 6 hours for free genistein ... and 3 to 8 hours for total genistein (aglycone + conjugates ...). In one of the studies, the lowest dose used (2 mg/kg bw) was stated to provide more than twice the level of isoflavones ingested in a Japanese daily diet. A study in which menopausal women were given a 50 mg commercial isoflavone extract incorporated into fruit juice, chocolate, or a cookie showed no significant effect of the food matrix on genistein absorption or urinary excretion parameters. In a study in which 8 women were dosed with 0.4 or 0.8 mg/kg bw 13C-labeled genistein, the area under the curve (AUC) at the higher dose was less than double the AUC at the lower dose, suggesting a decrease in fractional absorption with increasing dose.
There is considerable individual variation in the absorption and metabolism of ingested genistin and genistein. There are some data suggesting that genistein may be more bioavailable than genistin. However, other data suggest that the extent of absorption of genistein is similar for the aglycone and the glucoside forms. There are little data available on the tissue distribution of genistein.
A recently completed study has also shown inter-individual variation in the urinary excretion of isoflavones and their metabolites following soy challenge in adults. In this study, 76 volunteers were fed either a high (104+/-24 mg total isoflavones/day) or low (0.5+/-0.5 mg total isoflavones/day) soya diet for 10 weeks. Volunteers on the high soya diet showed extensive urinary excretion of daidzein, genistein and their metabolites. Of the volunteers on the high soya diet 34% were identified as good equol excretors ( 1000 nmol/24 hours). Comparative analysis of the fecal flora between equol and non-equol producers was investigated, however, the microflora (bacteria) responsible for equol production could not be isolated and therefore, were not be identified
The pharmacokinetics of isoflavones in 10 healthy women were determined from serum appearance/disappearance concentration profiles and urinary excretions after single-bolus ingestion of 10, 20 or 40 g of soy nuts delivering increasing amounts of the conjugated forms of daidzein (6.6, 13.2 and 26.4 mg) and genistein (9.8, 19.6 and 39.2 mg). Peak serum daidzein and genistein concentrations were attained after 4-8 hr, and elimination half-lives were 8.0 and 10.1 hr, respectively. There were no differences in the pharmacokinetics of daidzein and genistein between pre- and postmenopausal women, indicating absorption and disposition of isoflavones to be independent of age or menopausal status. A curvilinear relationship was observed between the bioavailability of daidzein and genistein, apparent from the area under the curve to infinity (AUC(inf)) of the serum concentration-time profiles and the amount of isoflavones ingested. The mean fraction of the isoflavones excreted in urine decreased with increasing intake when expressed as a percentage of the administered dose (63.2 + or - 8.0, 54.4 + or - 8.1 and 44.0 + or - 4.3%, respectively, for daidzein, and correspondingly, 25.2 + or - 5.3, 13.4 + or - 2.1 and 15.8 + or - 2.7% for genistein), underscoring the trend toward nonlinear pharmacokinetics. Equol was identified as a metabolite in 30% of women; it was present consistently in urine and blood from the same subjects. Its delayed appearance was consistent with colonic synthesis. On the basis of the pharmacokinetics, optimum steady-state serum isoflavone concentrations would be expected from modest intakes of soy foods consumed regularly throughout the day rather than from a single highly enriched product. [Setchell KD et al; J Nutr 133 (4): 1027-35 (2003)] PubMed Abstract
... After intestinal absorption, circulating genistein and daidzein are eliminated primarily by the kidneys. This study was undertaken to assess the metabolism of genistein and daidzein in patients with end-stage renal disease (ESRD) on hemodialysis therapy, and to test whether this treatment modality can replace the lack of kidney function, with respect to the elimination of the isoflavones. Twenty-three hemodialysis patients and 10 healthy subjects were studied. While consuming a self-selected low isoflavone diet, baseline blood levels were undetectable in eight of 10 healthy subjects and in 14 of 23 dialysis patients. The remaining participants had detectable levels, with the nine dialysis patients displaying much higher blood concentrations than the two healthy control subjects /with detectable levels/. After the evening intake of one dose of an isoflavone-rich soy protein isolate drink, the early morning blood levels of genistein and daidzein were higher in seven dialysis patients than in eight healthy subjects (genistein 1271+/-321 versus 425+/-104, PPubMed Abstract
Amniotic fluid samples (n=59) from women (n=53) undergoing routine amniocentesis between 15 and 23 weeks of gestation were analyzed by gas chromatography/mass spectrometric (GC/MS). Analytes included the phytoestrogens daidzein, genistein, formononetin, biochanin A, and coumestrol. Dietary phytoestrogens were quantified in 96.2% of second trimester amniotic fluid samples tested. The mean (+/- standard deviation (S.D.)) concentration of daidzein and genistein in amniotic fluid was 1.44 +/- 1.34 and 1.69 +/- 1.48 ng/mL with maximum levels of 5.52 and 6.54 ng/mL, respectively. Second trimester amniotic fluid contains quantifiable levels of dietary phytoestrogens and thus is a marker of mid pregnancy fetal exposure. [Foster WG et al; Toxicol Lett 129 (3): 199-205 (2002)] PubMed Abstract
Three papers reported that genistein is distributed to the human conceptus. Adlercreutz et al. used a GC/MS method to measure maternal plasma, cord plasma, and amniotic fluid phytoestrogen levels in 7 healthy omnivorous Japanese women (20-30 years old) who had just given birth. Only the results for genistein are discussed here. ... Genistein was detected in cord blood and amniotic fluid, and levels were reported to be variable between subjects. Correlations between maternal blood and cord blood or amniotic fluid genistein levels were not statistically significant. Most of the genistein in amniotic fluid was represented by glucuronide or sulfoglucuronide conjugates. [Unconjugated and sulfate conjugates of genistein represented 10-15% of total genistein in cord blood and amniotic fluid.] The study authors concluded that phytoestrogens cross the placenta. Foster et al. measured phytoestrogens in 57 human amniotic fluid samples collected between 15 and 23 weeks of gestation. Samples were collected in Los Angeles [ethnic composition and dietary factors not discussed]. Measurements were made by GC/MS after glucuronidase treatment to hydrolyze the conjugates. Genistein was measurable in 42 of the samples with a mean +/- SD concentration of 1.08 +/-0.91 ng/mL [4.0 +/-3.4 nM] (range 0.4-4.86 ng/mL [1.5-17.9 nM]). In a different paper, these authors reported genistein concentrations in 59 amniotic fluid samples obtained from 53 pregnant women at 15-23 weeks of gestation (4 sets of twins and 1 woman who was sampled 3 times). There were 42 women with measurable amniotic fluid genistein concentrations. The mean +/- SD genistein concentration was 1.69 +/- 1.48 ng/mL [6.25 +/- 5.48 nM] (maximum 6.54 ng/mL [24.2 nM]). [In a table, the mean +/- SD is reported as 1.37 +/- 1.00 ng/mL (5.07 +/- 3.7 nM) with a median of 0.99 ng/mL (3.7 nM). It is not known whether there are any samples represented in both papers.] Engel et al. measured genistein in amniotic fluid samples obtained prior to 20 weeks. The samples were collected for the sole indication of ?advanced maternal age? (>35 years). The median (range) genistein concentration was 1.38 (0.20-7.88) g/L.
In reviews that primarily addressed genistein exposure through soy product intake, it was reported that most ingested genistein is excreted in urine, with very little excreted in feces. Isoflavone excretion has been reported at about 30% in urine and 1 to 4% in feces. These fecal excretion data are in contrast to experimental animal data, which show fecal excretion of 14C-genistein and/or derivatives at 30 to 36% of dose. (A strong possibility must be entertained that some of the material escaped detection due to bacterial degradation ... ).
.. This study describes the internal exposures of post-natal day 10 (PND10) /Sprague-Dawley/ rat pups due to lactational transfer of genistein. Conjugated and aglycone forms of genistein were measured by using LC/MS/MS in serum (PND10) and milk (PND7) from lactating dams consuming a genistein-fortified soy-free diet, and in serum from their pups at a time when milk was the only food source (PND10). This study shows that limited lactational transfer of genistein to rat pups occurs and that internal exposures to the active aglycone form of genistein are generally lower than those measured previously in the fetal period. [Doerge DR et al; Reprod Toxicol 21 (3): 307-12 (2006)] PubMed Abstract
... The goal of the present study was to measure placental transfer of genistein in rats as a possible route of developmental exposure. Pregnant Sprague-Dawley rats were administered genistein orally, either by diet or by gavage. Concentrations of genistein aglycone and conjugates were measured in maternal and offspring serum and brain using HPLC with isotope dilution electrospray tandem mass spectrometry. Although fetal or neonatal serum concentrations of total genistein were approximately 20-fold lower than maternal serum concentrations, the biologically active genistein aglycone concentration was only 5-fold lower. Fetal brain contained predominately genistein aglycone at levels similar to those in the maternal brain. These studies show that genistein aglycone crosses the rat placenta and can reach fetal brain from maternal serum genistein levels that are relevant to those observed in humans. [Doerge DR et al; Reprod Toxicol 15 (2): 105-10 (2001)] PubMed Abstract
Mass balance, plasma pharmacokinetics, tissue distribution, and metabolism of carbon-14-genistein were investigated in male and female rats (n = 5) following an oral dose of (14-C)genistein (4 mg/kg) to determine potential sites and mechanisms of biological action. Mean total excretion of radioactivity in urine and feces for both sexes was 66 and 33% of the dose respectively at 166 hr after administration. Mean and maximal concentrations of radioactivity in plasma were significantly (P PubMed Abstract
Genistein (4 or 40 mg/kg) was administered to pregnant Sprague-Dawley rats by oral gavage daily from gestation day (GD) 5 through 19 or on GD 19 alone. Maternal and GD 19 fetal tissues were collected 0.5, 1, 2, 4, 6, 8, 12, and 24 hr following administration of the final dose on GD 19. Concentrations of genistein, genistein glucuronide, and genistein sulfate were quantitated by LC-MS/MS. In maternal plasma, genistein glucuronide was the predominant metabolite. In the fetal plasma, genistein glucuronide and genistein sulfate were the primary metabolites. Genistein levels in maternal and fetal plasma were much lower than its conjugates. The concentration of genistein in placental tissue was higher than either conjugate. Fetal concentrations of unconjugated genistein following administration of 40 mg/kg were above the EC50 for ERbeta activation. Repeated administration of 40 mg/kg genistein resulted in minor changes in genistein kinetics in the pregnant rat compared to single administration of the same dose. These data suggest that conjugated forms of genistein are not transported across the placenta. High placental concentrations of genistein indicate the placenta is a potential target organ for genistein action during gestation. [Soucy NV et al; Toxicol Sci 90 (1): 230-40 (2006)] PubMed Abstract
Genistein, the principal soy isoflavone, was administered in the diet to male and female Sprague-Dawley rats as part of a multigeneration study of potential endocrine modulation. The rats were exposed to genistein in utero, through maternal milk, and as adults through postnatal day 140 via essentially isoflavone-free feed (approximately 0.5 ug/g) fortified at 5, 100 and 500 ug/g with genistein aglycone. Analytical methods based on liquid chromatography, mass spectrometry and the use of deuterated genistein were developed and validated for use in measuring genistein in serum and tissues. Pharmacokinetic analysis of serum genistein showed a significant difference (P PubMed Abstract
The intestinal absorption, biliary excretion and metabolism of genistein ... was examined in anesthetized, adult female rats fitted with indwelling biliary cannulas. 4-14C-Genistein, when infused into the duodenum, was rapidly absorbed from the intestine, taken up by the liver and excreted into the bile as its 7-O-beta-glucuronide conjugate. Cumulative recovery of 14C-radioactivity in the bile over a 4-hr period was 70-75% of the dose. When genistein was infused into the portal vein, it was also taken up efficiently by the liver, conjugated with glucuronic acid and transported into bile. However, portal blood collected after duodenal infusions of genistein contained mostly genistein 7-O-beta-glucuronide, suggesting that in vivo glucuronidation occurred in the intestinal wall rather than the liver. This was confirmed using everted intestinal sac preparations. Reinfusion of genistein 7-O-beta-glucuronide into the duodenum or into the mid small intestine resulted in its reappearance in the bile, albeit more slowly than when genistein was infused. Over a 4-hr collection period, the cumulative recovery of 14C-radioactivity in bile was 27 and 70-75% of the administered dose for duodenal and ileal infusions, respectively. These data indicate that genistein is highly bioavailable in rats and because of its enterohepatic circulation may accumulate within the gastrointestinal tract. [Sfakianos J et al; J Nutr 127 (7): 1260-8 (1997)] PubMed Abstract
The present study describes an in vivo bioavailability experiment for genistein and its glycoside genistin, either as pure compounds or from a soy protein isolate extract, using freely moving unanesthetized rats with a cannulation in the portal vein. The results show that genistein is readily bioavailable, being observed in portal vein plasma at the first point of detection at 15 min after dosing. The AUC(0-24hr) values for total genistein and its conjugates were 54, 24, and 13 uM hr for genistein, genistin, and an enriched protein soy extract, respectively. These results indicate that the bioavailability of genistein is higher for the aglycon than for its glycoside. Genistin is partly absorbed in its glycosidic form. It is concluded that bioavailability studies based on portal vein plasma levels contribute to insight into the role of the intestine and liver in deglycosylation and uptake characteristics of glycosylated flavonoids. [Steensma A et al; J Agric Food Chem 54 (21): 8006-12 (2006)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6,500(SRC), determined from a structure estimation method(2), indicates that genistein is expected to be immobile in soil(SRC). The estimated pKa of genistein is 7.63(3), indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of genistein from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.1X10-17 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Genistein is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.2X10-12 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation data were not available(SRC, 2007).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6,500(SRC), determined from a structure estimation method(2), indicates that genistein is expected to adsorb to suspended solids and sediment(SRC). The estimated pKa value of 7.63(3) indicates genistein will exist partially in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(4), an estimated BCF of 4.5(SRC), from an estimated log Kow of 2.84(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2007).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), genistein, which has an estimated vapor pressure of 5.2X10-12 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase genistein may be removed from the air by wet or dry deposition(SRC). A UV max of 262.2 nm(3) indicates that genistein is not susceptible to direct photolysis(SRC).

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