CAS Number479-13-0
Synonyms3,9-Dihydroxycoumestan; EINECS 207-525-6; Cumoesterol; Cumoestrol; MFCD00016885; 7',6-Dihydroxycoumarino(3',4',3,2)coumarone; 3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one; Coumestrol; Cumostrol; 3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one; 7,12-Dihydroxycoumestan; coumesterol; 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one; 2-(2,4-Dihydroxyphenyl)-6-hydroxy-3-benzofurancarboxylic Acid d-Lactone
Molecular FormulaC15H8O5
Molecular Weight268.22
Purity≥95.0 (HPLC)%
Density1.6±0.1 g/cm3
Boiling Point406.0±24.0 °C at 760 mmHg
Melting Point≥350 °C (lit.)
Appearancepowder
EINECS207-525-6
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 479-13-0 |
| Catalog No. | 2A-9009922 |
| Chinese Name | 拟雌内酯 |
| Synonyms | 3,9-Dihydroxycoumestan; EINECS 207-525-6; Cumoesterol; Cumoestrol; MFCD00016885; 7',6-Dihydroxycoumarino(3',4',3,2)coumarone; 3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one; Coumestrol; Cumostrol; 3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one; 7,12-Dihydroxycoumestan; coumesterol; 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one; 2-(2,4-Dihydroxyphenyl)-6-hydroxy-3-benzofurancarboxylic Acid d-Lactone |
| Molecular Formula | C15H8O5 |
| Molecular Weight | 268.22 |
| Purity | ≥95.0 (HPLC) |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 406.0±24.0 °C at 760 mmHg |
| Melting Point | ≥350 °C (lit.) |
| Appearance | powder |
| Water Solubility | DMSO: soluble |
| Storage Condition | Refrigerator |
| Application | Coumestrol is a phytoestrogen found in soy products. Potential therapeutic activity against cancer, neurological disorders and autoimmune diseases. The IC50 value for inhibiting ES2 cell proliferation |
| EINECS | 207-525-6 |
| PubChem ID | 57648279 |
| MDL Number | MFCD00016885 |
| SMILES | Oc1ccc-2c(OC(=O)c3c-2oc4cc(O)ccc34)c1 |
| InChI | 1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H |
| InChI Key | ZZIALNLLNHEQPJ-UHFFFAOYSA-N |
| Beilstein/REAXYS | 266702 |
| NACRES Code | NA.77 |
| UNSPSC | 41116107 |
| Hazard Symbols | Transport |
| MSDS | msds/9922_1_479_13_0.pdf |
| Bioactivity | Coumestrol, a phytoestrogen present in soybean products, exhibits activities against cancers, neurological disorders, and autoimmune diseases. It suppresses proliferation of ES2 cells with an IC50 of 50 μM. Related Catalog Signaling Pathways >> Others >> Estrogen Receptor/ERR Research Areas >> Cancer Natural Products >> Phenylpropanoids Target IC50: 50 μM[1] In Vitro Coumestrol exerts chemotherapeutic effects via PI3K and ERK1/2 MAPK pathways. Coumestrol inhibits viability and invasion, and induces apoptosis of ES2 (clear cell-/serous carcinoma origin) cells. In addition, immunoreactive PCNA and ERBB2, markers of proliferation of ovarian carcinoma, are attenuated in their expression in coumestrol-induced death of ES2 cells. Phosphorylation of AKT, p70S6K, ERK1/2, JNK1/2 and p90RSK is inactivated by coumestrol treatment in a dose- and time-dependent manner[1]. Coumestrol inhibits proliferation and induces apoptosis in MCF-7 cells, which is prevented by copper chelator neocuproine and ROS scavengers. Coumestrol treatment induces ROS generation coupled to DNA fragmentation, up-regulation of p53/p21, cell cycle arrest at G1/S phase, mitochondrial membrane depolarization and caspases 9/3 activation[2]. Cell Assay To determine dose-dependent effects of coumestrol, ES2 cells are treated with different concentrations (0, 1, 10, 20, 50 or 100 μM) of coumestrol[1]. Coumestrol is dissolved in DMSO to prepare a 3 mM stock. Breast cancer MCF-7 cells are treated with increasing concentrations of coumestrol for 24, 48 and 72 h. Then, 20 μL of MTT (5 mg/mL) is added each well and re-incubated for additional 3 h. Formazan blue crystals formed are dissolved in 100 μL of DMSO. Absorbance is read at 570 nm using ELISA plate reader[2]. References [1]. Lim W, et al. Coumestrol suppresses proliferation of ES2 human epithelial ovarian cancer cells. J Endocrinol. 2016 Mar;228(3):149-60. [2]. Zafar A, et al. Cytotoxic activity of soy phytoestrogen coumestrol against human breast cancer MCF-7 cells: Insights into the molecular mechanism. Food Chem Toxicol. 2017 Jan;99:149-161. Chemical & Physical Properties Density 1.6±0.1 g/cm3 Boiling Point 406.0±24.0 °C at 760 mmHg Melting Point ≥350ºC(lit.) Molecular Formula C15H8O5 Molecular Weight 268.221 Flash Point 199.3±22.9 °C Exact Mass 268.037170 PSA 83.81000 LogP 2.94 Vapour Pressure 0.0±1.0 mmHg at 25°C Index of Refraction 1.768 InChIKey ZZIALNLLNHEQPJ-UHFFFAOYSA-N SMILES O=c1oc2cc(O)ccc2c2oc3cc(O)ccc3c12 Storage condition Refrigerator Water Solubility DMSO: soluble |
| Use of | Properties Name coumestrol Synonym More Synonyms Coumestrol Biological Activity Related Catalog Signaling Pathways >> Others >> Estrogen Receptor/ERR Research Areas >> Cancer Natural Products >> Phenylpropanoids IC50: 50 μM[1] References [1]. Lim W, et al. Coumestrol suppresses proliferation of ES2 human epithelial ovarian cancer cells. J Endocrinol. 2016 Mar;228(3):149-60. Chemical & Physical Properties Molecular Formula C15H8O5 Exact Mass 268.037170 PSA 83.81000 Index of Refraction 1.768 InChIKey ZZIALNLLNHEQPJ-UHFFFAOYSA-N Storage condition Refrigerator Water Solubility DMSO: soluble |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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