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Related CAS#:
479-13-0 796089-78-6
35826-57-4 3172-99-4
18642-23-4

479-13-0

479-13-0 structure
479-13-0 structure
  • Name: Coumestrol
  • Chemical Name: coumestrol
  • CAS Number: 479-13-0
  • Molecular Formula: C15H8O5
  • Molecular Weight: 268.221
  • Catalog: Natural product Coumarin
  • Create Date: 2018-07-08 15:21:36
  • Modify Date: 2024-01-02 16:37:10
  • 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.
Name coumestrol
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
6H-Benzofuro[3,2-c][1]benzopyran-6-one, 3,9-dihydroxy-
2-(2,4-Dihydroxyphenyl)-6-hydroxy-3-benzofurancarboxylic Acid d-Lactone
Description 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
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.

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
Storage condition Refrigerator
Water Solubility DMSO: soluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DF8077000
CHEMICAL NAME :
6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-
CAS REGISTRY NUMBER :
479-13-0
BEILSTEIN REFERENCE NO. :
0266702
LAST UPDATED :
199801
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C15-H8-O5
MOLECULAR WEIGHT :
268.23
WISWESSER LINE NOTATION :
T D6 B566 CO KVOJ FQ OQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
2500 ug/kg
SEX/DURATION :
lactating female 1-5 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Maternal Effects - other effects Endocrine - estrogenic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
234 mg/kg
SEX/DURATION :
female 1-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
35 gm/kg
SEX/DURATION :
female 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) Reproductive - Effects on Embryo or Fetus - other effects to embryo
TYPE OF TEST :
Unscheduled DNA synthesis

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
10 umol/L
REFERENCE :
FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 35,605,1997
Hazard Codes Xn: Harmful;
Risk Phrases R22
Safety Phrases 26-36
WGK Germany 3
RTECS DF8077000

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