Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
제니스테인
제니스테인 · Licoisoflavone · 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one · GEN · GENESTEIN · Bonistein · 5,7,4'-TRIHYDROXYISOFLAVONE · prunetol
식별자 및 물리적 특성
| CAS No. | 446-72-0 |
|---|---|
| 분자식 | C15H10O5 |
| 평균 분자량 | 270.24 g/mol |
| 단동위원소 질량 | 270.05282342 g/mol |
| SMILES | O=c1c(-c2ccc(O)cc2)coc2cc(O)cc(O)c12 |
| InChIKey | TZBJGXHYKVUXJN-UHFFFAOYSA-N |
| PubChem CID | 5280961 |
| ChEMBL | CHEMBL44 |
| ChEBI | CHEBI:28088 |
| EC No. | 207-174-9 |
| DTXSID | DTXSID5022308 |
| 현지명 | 제니스테인 |
화학 및 물리적 성질
| XLogP | 2.7 |
|---|---|
| 극성 표면적 | 87 |
| 수소 결합 공여자 수 | 3 |
| 수소 결합 수용자 수 | 5 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 20 |
| 형식 전하 | 0 |
| 복잡도 | 410 |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| 지질 | Polyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205] |
| Polymers | Antioxidant (polyphenol) |
| 화장품 | Cosmetics ingredient -> Conditioning/Emollient |
| Color/Form | Rectangular or six-sided rods from 60% alcohol. Dendritic needles from ether |
| 용해도 | Soluble in the usual organic solventssoluble in dilute alkalies with yellow color. Practically insoluble in water.DMSO: 용해될 수 있다 |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 녹는점 | 297-298 °C (slight decomposition)301.5 °C |
| Physical Description | Solid |
| Collision Cross Section | 160.3 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID5022308]177.67 Ų [M+Na]+ [CCS Type: DTMethod: stepped-field]165.96 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]156.5 Ų [M+H]+ [CCS Type: TW176.5 Ų [M+Na]+ |
| 끓는 점 | 333.35°C (rough estimate) |
| 밀도 | 1.2319 (rough estimate) |
| 굴절률 | 1.6000 (estimate) |
| 저장 조건 | -20°C |
| 물리적 상태 | 가루 |
| pKa(산도 계수) | 6.51±0.20(Predicted) |
| 색상 | 회백색 |
| 생물학적 소스 | synthetic |
| 용해도 | 불용성 |
| Merck | 14,4391 |
| BRN | 263823 |
| 안정성 | 감광성 |
| 화장품 원료 기능 | 피부 컨디셔닝 - 기타 |
| 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 |
| InChIKey | TZBJGXHYKVUXJN-UHFFFAOYSA-N |
| SMILES | Oc1ccc(cc1)C2=COc3cc(O)cc(O)c3C2=O |
| LogP(분배 계수) | 3.114 (est) |
| EPA | 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)- (446-72-0) |
화학적 성질
Yellow Crystalline Solid
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 6.8% (6 of 88) of reports.WarningH302 (87.5%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 88 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Hazard Traits - Developmental ToxicityEndocrine Toxicity4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Special Reports | National Toxicology Program, Center For the Evaluation of Risks To Human ReproductionNTP-CERHR Expert Panel Report on the Reproductive and Developmental Toxicity of Genistein(NTP-CERHR-GENISTEIN-06) April 2006. This evaluation results from the effort of a 14-member panel of government and non-government scientists that culminated in a public expert panel meeting held March 15-17, 2006. ... This Expert Panel Report will be included in /a/ subsequent NTP-CERHR Monograph on the Potential Human Reproductive and Developmental Effects of Genistein.Hughs I, Woods HFCommittee on Toxicity of Chemicals in Food, Consumer Products and the Environment Phytoestrogens and Health. UK Food Standards Agency, 444 p. (May 2003). This report of the Committee on Toxicity of Chemicals in Food, Consumer Products and the Environment (COT) considers the public health implications of exposure to phytoestrogens in the diet. The report was drafted by a specially convened Working Group of the Committee to advise on the health implications of dietary phytoestrogens through review of published scientific research and the UK Food Standards Agency's phytoestrogen research program. |
| Hazard Classes and Categories | Acute Tox. 4 (87.5%) |
| 처리 방법 | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| 체내 부담 | Genistein was detected in 179 of 199 urine samples at concn ranging from 1.1 (detection limit) to 4,140 ppb(1). In Japanese people consuming a traditional diet high in soy products, an average plasma concentration of 250 nM has been measured(2). |
| 상호 작용 | Humans and wildlife are frequently exposed to mixtures of endocrine active-compounds (EAC). The objective of the present study was to investigate the potential of the phytoestrogen genistein to influence the reproductive developmental toxicity of the endocrine-active pesticide methoxychlor. Three levels of genistein (0, 300, or 800 ppm) and two levels of methoxychlor (0 or 800 ppm) were used in this study. Sprague-Dawley rats were exposed to the two compounds, either alone or in combinations, through dietary administration to dams during pregnancy and lactation and to the offspring directly after weaning. Both compounds, methoxychlor in particular, were associated with reduced body growth at 800 ppm, but pregnancy outcome was not affected by either treatment. An acceleration of vaginal opening (VO) in the exposed female offspring was the only observed effect of genistein at 300 ppm. Exposure to 800 ppm genistein or 800 ppm methoxychlor caused accelerated VO and also altered estrous cyclicity toward persistent estrus in the female offspring. The estrogenic responses to genistein and methoxychlor administered together were apparently accumulative of the effects associated with each compound alone. Methoxychlor, but not genistein, delayed preputial separation (PPS) in the male rats. When administered with methoxychlor, genistein at 800 ppm enhanced the effect of methoxychlor on delaying PPS. Genistein and methoxychlor treatment did not change gender-specific motor activity patterns in either sex. To explore possible mechanisms for interaction between the two compounds on development, we performed estrogen receptor (ER)- and androgen receptor (AR)-based in vitro transcriptional activation assays using genistein and the primary methoxychlor metabolite 2,2-bis-(p-hydroxyphenyl)-1,1,1-trichloroethane (HPTE). While the in vitro assays supported the estrogenic effects of genistein and methoxychlor and the antiandrogenic effects of methoxychlor, the reactivity of these compounds with ERs alpha and beta could not predict the greater in vivo estrogenic potency of methoxychlor over genisteinnor could the potentiation of the methoxychlor effect on PPS by genistein be predicted based on in vitro HPTE and genistein reactions with the AR. Data from this study indicate that phytoestrogens are capable of altering the toxicological behaviors of other EACs, and the interactions of these compounds may involve complexities that are difficult to predict based on their in vitro steroid receptor reactivities.... Interactions between the soy isoflavone, genistein, and an antiestrogen, tamoxifen (TAM), on the growth of estrogen (E)-dependent breast cancer (MCF-7) cells implanted in ovariectomized athymic mice /were investigated/. ... Six treatment groups were used: control (C)0.25 mg estradiol (E2) implant (E)E2 implant + 2.5 mg TAM implant (2.5 TE)E2 implant + 2.5 mg TAM implant + 1000 ppm genistein (2.5 TEG)E2 implant + 5 mg TAM implant (5 TE), and E2 implant +5 mg TAM implant +1000 ppm genistein (5 TEG). Treatment with TAM (2.5 TE and 5 TE) suppressed E2-stimulated MCF-7 tumor growth in ovariectomized athymic mice. Dietary genistein negated/overwhelmed the inhibitory effect of TAM on MCF-7 tumor growth, lowered E2 level in plasma, and increased expression of E-responsive genes (e.g., pS2, PR, and cyclin D1). ... Caution is warranted for postmenopausal women consuming dietary genistein while on TAM therapy for E-responsive breast cancer.The anticancer agent genistein inhibits cell growth of tumor cell lines from various malignancies. ... /The authors/ investigated the effectiveness of combined treatment of ionizing radiation (IR) with genistein on cervical HeLa cells and its possible mechanism. It was found that the inhibitory rate in cells with combined treatment was significantly higher than that of the cells treated with IR or genistein alone. After treatments of IR (4 Gy) combined with genistein (40 micromol/L), the apoptotic index of the cells was significantly increased and the cells were arrested in the G2/M phase. Survivin mRNA expression increased after IR (4 Gy), while it significantly decreased after combined treatment. These findings indicated that genistein enhanced the radiosensitivity of cervical cancer HeLa cells, and the mechanisms for this action might include increase of apoptosis, decrease of survivin expression, and prolongation of cell cycle arrest. |
| 환경 거동 | 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 °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). |
| 식품 조사 수치 | The genistein content in tofu, tempeh, and soy flour has been measured at 14, 25, and 71 mg, respectively (aglycone and glycosides)(1). |
| 독성 요약 | 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. [1] 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. [1] |
| Average Daily Intake | In Japan, the average dietary genistein intake has been deteremined to be in the range of 8 to 12 mg/day/person(1). |
| 생태독성 발췌 | /BIRDS and MAMMALS/ ... /The authors/ orally dosed zebra finch chicks daily during their linear growth phase (days 5-11) with estradiol benzoate (EB), genistein, methoxychlor, or octylphenol, all dissolved or suspended in canola oil, or canola oil alone, as a vehicle control. On day 12, oviducts were removed, weighed and examined histologically. All doses of EB (0.1-1,000 nmol/g body weight), genistein at 100 nmol/g, and methoxychlor and octylphenol at 1,000 nmol/g, markedly increased oviduct weight, with the highest dose of EB inducing a 60-fold increase over controls./BIRDS and MAMMALS/ The aim of the present study was to investigate the chronic effects of dietary phytoestrogens, genistein (8 mg/kg/ day) and beta-sitosterol (50 mg/kg/day), on the weight regulation of the mink (Mustela vison). The parental generation was exposed from August 2002 to May-June 2003 to either beta-sitosterol or genistein, while the kits were exposed through gestation and lactation. Food consumption and body masses were monitored monthly. Plasma lipid, glucose, total protein and hormone (ghrelin, leptin, triiodothyronine and thyroxine) concentrations were measured from the parents in August 2002, January 2003 and at the end of the experiment in May-June 2003 when the kits were 21 days of age. Relative food intake was higher in the beta-sitosterol-exposed minks than in the control or genistein minks in September 2002. ... Plasma ghrelin levels and liver phosphorylase activities of the mink kits were higher due to genistein exposure. In mink kits, exposure to both phytoestrogens reduced the plasma thyroxine concentrations. The kidney glycogen concentrations and the muscle phosphorylase activities of phytoestrogen-treated adult minks were elevated. The results of this study suggest that minks are sensitive to perinatal phytoestrogen exposure./AQUATIC SPECIES/ Twelve chemicals were tested for binding affinity to rainbow trout liver estrogen receptor (rbtER) and fathead minnow liver ER (fhmER). The chemicals included ... genistein .... . Relative binding affinity (RBA) was calculated for each chemical as a function of E2 binding to the receptor. ... Relative binding affinity of genistein for both fhmER and rbtER were moderate, with values between 0.3 and 5%. .../AQUATIC SPECIES/ /The authors/ investigated the behavioral effects of exposure to waterborne phytoestrogens in male fighting fish, Betta splendens. Adult fish were exposed to a range of concentrations of genistein, equol, beta-sitosterol, and the positive control 17beta-estradiol. The following behaviors were measured: spontaneous swimming activity, latency to respond to a perceived intruder (mirror reflection), intensity of aggressive response toward a perceived intruder, probability of constructing a nest in the presence of a female, and the size of the nest constructed. We found few changes in spontaneous swimming activity, the latency to respond to the mirror, and nest size, and modest changes in the probability of constructing a nest. There were significant decreases, however, in the intensity of aggressive behavior toward the mirror following exposure to several concentrations, including environmentally relevant ones, of 17beta-estradiol, genistein, and equol. This suggests that phytoestrogen contamination has the potential to significantly affect the behavior of free-living fishes.For more Ecotoxicity Excerpts (Complete) data for GENISTEIN (6 total), please visit the HSDB record page. |
| Plant Concentrations | Genistein is a phytoestrogen found in soy and legumes(1). Genistein was detected in air-dried wood pulp from a Canadien bleached kraft mill at 30.0 ug/kg(2). |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=446-72-0] |
| Effluent Concentrations | Genistein was detected in untreated effluent at 13.1 ug/L and treated effluent at 10.5 ug/L from a bleached kraft mill in Ontario, Canada(1). Genistein was detected in the effluent of 8 of 18 sewage treatment plants tested in southwestern Germany at concentrations ranging from 2.7-38 ng/L(2). |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of genistein can be estimated to be 6,500(SRC). According to a classification scheme(2), this estimated Koc value suggests that genistein is expected to be immobile in soil. The estimated pKa value of 7.63(3), indicates 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). |
| Natural Pollution Sources | Genistein is a phytoestrogen found in soy, legumes(1) and wood pulp(2). |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | NR2392000 |
| 관세 코드 | 29329990 |
| 위험 문구(R) | 36/38-22 |
| 위험 표시 | Xi,Xn |
| 안전 문구(S) | 26-24/25-22 |
| 위험 등급 | IRRITANTAcute Tox. 4 Oral |
| 저장 분류 | 11 - Combustible Solids |
| 유해 물질 데이터 | 446-72-0(Hazardous Substances Data) |
용도
용도
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
일반 설명
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards