ethyl 2,2-bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate

• ChemBase ID: 168432
• Molecular Formular: C22H16O8
• Molecular Mass: 408.35764
• Monoisotopic Mass: 408.08451747
• SMILES: c1(C(c2c(=O)oc3c(c2O)cccc3)C(=O)OCC)c(c2c(oc1=O)cccc2)O
• Canonical SMILES: CCOC(=O)C(c1c(=O)oc2c(c1O)cccc2)c1c(=O)oc2c(c1O)cccc2
• InChI: InChI=1S/C22H16O8/c1-2-28-20(25)15(16-18(23)11-7-3-5-9-13(11)29-21(16)26)17-19(24)12-8-4-6-10-14(12)30-22(17)27/h3-10,15,23-24H,2H2,1H3
• InChIKey: JCLHQFUTFHUXNN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2,2-bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
• IUPAC Traditional name: ethyl biscoumacetate
• Synonyms: 4-Hydroxy-α-(4-hydroxy-2-oxo-2H-1-benzopyran-3-yl)-2-oxo-2H-1-benzopyran-3-acetic Acid Ethyl Ester; 3,3'-(Carboxymethylene)bis(4-hydroxycoumarin) Ethyl Ester; BOEA; Bis(4-hydroxy-2-oxo-2H-1-benzopyran-3-yl)acetic Acid Ethyl Ester; NSC 36366; Neodicoumarin; Neodicoumarol; Neodicumarinum; Neodicumarol; Pelentan; Stabilene; Trombarin; Trombil; Trombolysan; Tromexan; Tromexan Ethyl Acetate; Ethyl Biscoumacetate

Database IDs

• CAS Number: 548-00-5
• PubChem SID: 162262564
• PubChem CID: 54685524

CALCULATED PROPERTIES

• H Donor: 2
• LogD (pH = 5.5): 1.3529121
• LogD (pH = 7.4): -1.2914196
• Log P: 1.6678784
• Molar Refractivity: 104.9504 cm^3
• Polarizability: 40.098236 Å^3
• Polar Surface Area: 119.36 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true
• Acid pKa: 5.536424
• H Acceptors: 5

DETAILS

Toronto Research Chemicals - E900100

Anticoagulant.

REFERENCES

• Gruber, C.M., et al.: Fed. Proc., 10, 303 (1951)
• 28) Jones, G., et al.: J. Mol. Biol., 267, 727 (1951)
• Du, J., et al.: J. Biol. Chem., 281, 37416 (1951)