ethyl 7-(acetyloxy)-2-oxo-2H-chromene-3-carboxylate

• ChemBase ID: 156779
• Molecular Formular: C14H12O6
• Molecular Mass: 276.24148
• Monoisotopic Mass: 276.0633881
• SMILES: CCOC(=O)c1cc2ccc(cc2oc1=O)OC(=O)C
• Canonical SMILES: CCOC(=O)c1cc2ccc(cc2oc1=O)OC(=O)C
• InChI: InChI=1S/C14H12O6/c1-3-18-13(16)11-6-9-4-5-10(19-8(2)15)7-12(9)20-14(11)17/h4-7H,3H2,1-2H3
• InChIKey: SKVJGNVETVRDTL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 7-(acetyloxy)-2-oxo-2H-chromene-3-carboxylate
• IUPAC Traditional name: ethyl 7-(acetyloxy)-2-oxochromene-3-carboxylate
• Synonyms: Ethyl 7-acetoxycoumarin-3-carboxylate

Database IDs

• CAS Number: 13209-77-3
• MDL Number: MFCD00037372
• Beilstein Number: 288630
• PubChem SID: 162250916; 24845086
• PubChem CID: 688600

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.713899
• LogD (pH = 7.4): 1.713899
• Log P: 1.713899
• Molar Refractivity: 68.273 cm^3
• Polarizability: 26.503647 Å^3
• Polar Surface Area: 78.9 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: alcohols: soluble; DMF: soluble; DMSO: soluble
• Melting Point: 151 °C(lit.)
• Fluorescence: λex 386 nm; λem 445 nm in 0.1 M Tris pH 8.0 (esterase)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C14H12O6
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 00838

Application
suitable as fluorogenic substrate for esterases (hydrolized: pH-indicator, pKa 7.04 (Lit.))