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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: 2026-07-09 15:54:33
  • 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 Coumestrol (Synthetic)
Coumestrol, 10 mM in DMSO
COUMESTROL BIOREAGENT, SUITABLE FOR
7’, 6-Dihydroxycoumino(3’, 4’, 3, 2)Coumone
Nsc22842
EINECS 207-525-6
Cumoesterol
2-(2,4-dihydroxyphenyl)-6-hydroxy-3-benzofurancboxylicacidelta-lacton
MFCD00016885
cumoesterol
Coumestrol ( synthitic)
3,9-Dihydroxy-6H-benzofuro[3,2-c]chromen-6-one
Coumesterol
3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one
[2-(2,4-DIHYDROXYPHENYL)-6-HYDROXY-3-BENZOFURAN-CBOXYLIC ACID ALPHA-LACTONE]
3,9-dihydroxy-6-benzofuro[3,2-c]benzopyranone
Cumostrol
7,12-DIHYDROXYCOUMESTAN
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
7 12-DIHYDROXYCOUMESTAN
6H-Benzofuro[3,2-C]benzopyran-6-one, 3,9-dihydroxy
COUMESTROL(P)
COUMESTROL
2-(2,4-DIHYDROXYPHENYL)-6-HYDROXY-3-BENZOFURANCBOXYLIC ACID DELTA-LACTONE
3,9-Dihydroxy-6H-benzofuro[3,2-c]chromen-6-one , Coumestrol
3,9-Dihydroxycoumestan
7, 6-DIHYDROXYCOUMINO(3, 4, 3,2)COUMONE
2-(2,4-Dihydroxyphenyl)-6-hydroxy-3-benzofurancboxylic Acid δ-Lactone
2-c]benzopyran-6-one,3,9-dihydroxy-6h-benzofuro[
Cumoestrol
3,9-DIHYDROXY-6H-BENZOFURO[3,2-C]-BENZOPYRAN-6-ONE
7,12-DIHYDROXYCOUMESTANE
COUMOESTROL
7',6-Dihydroxycoumarino(3',4',3,2)coumarone
5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.02,.011,1]htadeca-1,2,3,5,11,12,14-htaen-9-one
2-(2 4-DIHYDROXYPHENYL)-6-HYDROXY-3-BENZOFURANCBOXYLIC ACID D-LACTONE
3-Benzofurancboxylic acid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, .delta.-lactone
2-c)benzopyran-6-one,3,9-dihydroxy-6h-benzofuro(
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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