2-[6-(carboxymethoxy)-3-oxo-3H-xanthen-9-yl]benzoic acid

• ChemBase ID: 153757
• Molecular Formular: C22H14O7
• Molecular Mass: 390.34236
• Monoisotopic Mass: 390.07395279
• SMILES: c1ccc(c(c1)c1c2ccc(cc2oc2cc(=O)ccc12)OCC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)COc1ccc2c(c1)oc1c(c2c2ccccc2C(=O)O)ccc(=O)c1
• InChI: InChI=1S/C22H14O7/c23-12-5-7-16-18(9-12)29-19-10-13(28-11-20(24)25)6-8-17(19)21(16)14-3-1-2-4-15(14)22(26)27/h1-10H,11H2,(H,24,25)(H,26,27)
• InChIKey: VQKDLLIKXLDPHW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[6-(carboxymethoxy)-3-oxo-3H-xanthen-9-yl]benzoic acid
• IUPAC Traditional name: 2-[3-(carboxymethoxy)-6-oxoxanthen-9-yl]benzoic acid
• Synonyms: FOAA; O′-(Carboxymethyl)fluorescein; Fluorescein-O′-acetic acid

Database IDs

• CAS Number: 233759-98-3
• MDL Number: MFCD05865263
• PubChem SID: 24888971; 162247896
• PubChem CID: 16218651

CALCULATED PROPERTIES

• Acid pKa: 2.9555237
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.6481133
• LogD (pH = 7.4): -4.167132
• Log P: 2.6368735
• Molar Refractivity: 113.9795 cm^3
• Polarizability: 38.689445 Å^3
• Polar Surface Area: 110.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Fluorescence: λex 455 nm; λem 514 nm in 0.1 M Tris pH 8.0

Safety Information

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

Product Information

• Purity: ≥90% (HPCE)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C22H14O7

DETAILS

Sigma Aldrich - 88596

Other Notes
Fluorescent label which reacts with amines after activation to give isomerically homogeneous derivatives1,2