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: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0^2,^7.0^1^1,^1^6]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

Database IDs

• CAS Number: 479-13-0
• EC Number: 207-525-6
• MDL Number: MFCD00016885
• Beilstein Number: 266702
• PubChem SID: 162221052; 24856835; 24856836
• PubChem CID: 5281707
• CHEMBL: 30707
• Chemspider ID: 4445024
• KEGG ID: C10205
• Unique Ingredient Identifier: V7NW98OB34
• Wikipedia Title: Coumestrol

CALCULATED PROPERTIES

• Acid pKa: 7.1109495
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.3868842
• LogD (pH = 7.4): 1.9285021
• Log P: 2.3973212
• Molar Refractivity: 69.6195 cm^3
• Polarizability: 28.706497 Å^3
• Polar Surface Area: 79.9 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; DMSO: soluble; Ether; Slightly Sol. in Methanol; Water (pH 11-12)
• Apperance: Pale Yellow Solid
• Melting Point: >300°C; ≥350 °C(lit.); 385 °C (decomp)
• Fluorescence: λex 377 nm; λem 437 nm in 0.1 M Tris pH 8.0

Safety Information

• Storage Condition: Refrigerator
• RTECS: DF8077000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... ESR1(2099), ESR2(2100)mouse ... Esr1(13982)rat ... Ar(24208)

Product Information

• Purity: ≥95.0% (HPLC); ≥97.5% (HPLC)
• Suitability: suitable for fluorescence
• Impurities: ≤10.0% water
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C15H8O5

DETAILS

Sigma Aldrich - 27885

Biochem/physiol Actions
Coumestrol has anti-estrogenic actions in the brain and pituitary, mediated through estrogen receptor-α.1

Sigma Aldrich - 27883

Biochem/physiol Actions
Coumestrol has anti-estrogenic actions in the brain and pituitary, mediated through estrogen receptor-α.1

Toronto Research Chemicals - C781000

This compound has estrogenic activity. It exhibits bright blue fluorescence in neutral or acid solution, and greenish-yellow fluorescence in strong alkali solution.

REFERENCES

• Wolfbeis, O.S. & K. Schaffner: Photochem. Photobiol., 32, 143(1980)
• Bickoff et al.: J.Am. Chem Soc. 80, 3969 (1958)