7-(acetyloxy)-2-oxo-2H-chromene-3-carboxylic acid

• ChemBase ID: 156751
• Molecular Formular: C12H8O6
• Molecular Mass: 248.18832
• Monoisotopic Mass: 248.03208798
• SMILES: CC(=O)Oc1ccc2cc(c(=O)oc2c1)C(=O)O
• Canonical SMILES: CC(=O)Oc1ccc2c(c1)oc(=O)c(c2)C(=O)O
• InChI: InChI=1S/C12H8O6/c1-6(13)17-8-3-2-7-4-9(11(14)15)12(16)18-10(7)5-8/h2-5H,1H3,(H,14,15)
• InChIKey: JPSXXVSPZSKYBA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-(acetyloxy)-2-oxo-2H-chromene-3-carboxylic acid
• IUPAC Traditional name: 7-(acetyloxy)-2-oxochromene-3-carboxylic acid
• Synonyms: 2H-1-Benzopyran-3-carboxylic acid; 3-Carboxyumbelliferyl acetate; 7-Acetoxycoumarin-3-carboxylic acid

Database IDs

• CAS Number: 81017-23-4
• MDL Number: MFCD00037371
• Beilstein Number: 241040
• PubChem SID: 162250888
• PubChem CID: 688599

CALCULATED PROPERTIES

• Acid pKa: 2.6758358
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.768819
• LogD (pH = 7.4): -2.524723
• Log P: 0.97786367
• Molar Refractivity: 58.7553 cm^3
• Polarizability: 22.62125 Å^3
• Polar Surface Area: 89.9 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: dioxane: soluble; DMF: soluble; DMSO: soluble; ethanol: soluble
• Melting Point: 208 °C(lit.)
• Fluorescence: λex 332 nm; λem 447 nm in 0.1 M potassium phosphate pH 8.0 (after enzyme digest)

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): C12H8O6

DETAILS

Sigma Aldrich - 00835

Application
suitable as fluorogenic substrate for acetylcholine esterase
7-Acetoxycoumarin-3-carboxylic acid is a fluorogenic substrate to measure catalytic actvity of peptide dendrimers (speicifically, esterolytic activity)1.
Other Notes
Fluorogenic substrate for carbonic anhydrase2