7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid

• ChemBase ID: 155838
• Molecular Formular: C10H6O5
• Molecular Mass: 206.15164
• Monoisotopic Mass: 206.02152329
• SMILES: c1cc(cc2c1cc(c(=O)o2)C(=O)O)O
• Canonical SMILES: Oc1ccc2c(c1)oc(=O)c(c2)C(=O)O
• InChI: InChI=1S/C10H6O5/c11-6-2-1-5-3-7(9(12)13)10(14)15-8(5)4-6/h1-4,11H,(H,12,13)
• InChIKey: LKLWLDOUZJEHDY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid
• IUPAC Traditional name: 7-hydroxy-2-oxochromene-3-carboxylic acid
• Synonyms: Umbelliferone-3-carboxylic acid; 7-Hydroxycoumarin-3-carboxylic acid

Database IDs

• CAS Number: 779-27-1
• MDL Number: MFCD00017491
• Beilstein Number: 384141
• PubChem SID: 24879225; 162249976
• PubChem CID: 5337757

CALCULATED PROPERTIES

• Acid pKa: 2.8512235
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.5311834
• LogD (pH = 7.4): -2.5683367
• Log P: 1.0670373
• Molar Refractivity: 49.6038 cm^3
• Polarizability: 18.770252 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: alcohols: soluble; DMF: soluble; DMSO: soluble
• Melting Point: 261 °C(lit.)
• pKa: 7.04
• Fluorescence: λex 342 nm; λem 447 nm (pH 4.0); λex 386 nm; λem 448 nm in 0.1 M Tris pH 9.0

Safety Information

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

Product Information

• Purity: ≥98.0% (TLC)
• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C10H6O5
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 55155

Application
suitable as pH-indicator
Other Notes
Immobilized on a support to give a pH sensor1