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479-13-0 molecular structure
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5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

ChemBase ID: 126724
Molecular Formular: C15H8O5
Molecular Mass: 268.22102
Monoisotopic Mass: 268.03717336
SMILES and InChIs

SMILES:
O=c1oc2cc(O)ccc2c2oc3c(ccc(O)c3)c12
Canonical SMILES:
Oc1ccc2c(c1)oc(=O)c1c2oc2c1ccc(c2)O
InChI:
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
InChIKey:
ZZIALNLLNHEQPJ-UHFFFAOYSA-N

Cite this record

CBID:126724 http://www.chembase.cn/molecule-126724.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one
IUPAC Traditional name
coumestrol
Synonyms
Coumestrol
7,12-Dihydroxycoumestan
Coumestrol
3,9-Dihydroxy-6H-benzofuro[3,2-c]-[1]benzopyran-6-one
2-(2,4-Dihydroxyphenyl)-6-hydroxy-3-benzofurancarboxylic Acid δ-Lactone
Coumesterol
NSC 22842
CAS Number
479-13-0
EC Number
207-525-6
MDL Number
MFCD00016885
Beilstein Number
266702
PubChem SID
24856835
162221052
24856836
PubChem CID
5281707
CHEMBL
30707
Chemspider ID
4445024
KEGG ID
C10205
Unique Ingredient Identifier
V7NW98OB34
Wikipedia Title
Coumestrol

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 7.1109495  H Acceptors
H Donor LogD (pH = 5.5) 2.3868842 
LogD (pH = 7.4) 1.9285021  Log P 2.3973212 
Molar Refractivity 69.6195 cm3 Polarizability 28.706497 Å3
Polar Surface Area 79.9 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
DMSO: soluble expand Show data source
Ether expand Show data source
Slightly Sol. in Methanol expand Show data source
Water (pH 11-12) expand Show data source
Apperance
Pale Yellow Solid expand Show data source
Melting Point
>300°C expand Show data source
≥350 °C(lit.) expand Show data source
385 °C (decomp) expand Show data source
Fluorescence
λex 377 nm; λem 437 nm in 0.1 M Tris pH 8.0 expand Show data source
Storage Condition
Refrigerator expand Show data source
RTECS
DF8077000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Gene Information
human ... ESR1(2099), ESR2(2100)mouse ... Esr1(13982)rat ... Ar(24208) expand Show data source
Purity
≥95.0% (HPLC) expand Show data source
≥97.5% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
suitable for fluorescence expand Show data source
Impurities
≤10.0% water expand Show data source
Product Line
BioReagent expand Show data source
Empirical Formula (Hill Notation)
C15H8O5 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - 27885 external link
Biochem/physiol Actions
Coumestrol has anti-estrogenic actions in the brain and pituitary, mediated through estrogen receptor-α.1
Sigma Aldrich - 27883 external link
Biochem/physiol Actions
Coumestrol has anti-estrogenic actions in the brain and pituitary, mediated through estrogen receptor-α.1
Toronto Research Chemicals - C781000 external link
This compound has estrogenic activity. It exhibits bright blue fluorescence in neutral or acid solution, and greenish-yellow fluorescence in strong alkali solution.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Wolfbeis, O.S. & K. Schaffner: Photochem. Photobiol., 32, 143(1980)
  • • Bickoff et al.: J.Am. Chem Soc. 80, 3969 (1958)
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PATENTS

PATENTS

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INTERNET

INTERNET

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