CAS 479-13-0|Coumestrol

Introduction：Basic information about CAS 479-13-0|Coumestrol, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Coumestrol BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Synonyms

Common Name	Coumestrol
CAS Number	479-13-0	Molecular Weight	268.221
Density	1.6±0.1 g/cm3	Boiling Point	406.0±24.0 °C at 760 mmHg
Molecular Formula	C₁₅H₈O₅	Melting Point	≥350ºC(lit.)
MSDS	/	Flash Point	199.3±22.9 °C

Names

Name	coumestrol
Synonym	More Synonyms

Coumestrol BiologicalActivity

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	Signaling Pathways >>Others >>Estrogen Receptor/ERRResearch Areas >>CancerNatural 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

Toxicological Information

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

Safety Information

Hazard Codes	Xn: Harmful;
Risk Phrases	R22
Safety Phrases	26-36
WGK Germany	3
RTECS	DF8077000

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

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