ethyl 2-{[2-methyl-8-(4-methylbenzenesulfonamido)quinolin-6-yl]oxy}acetate

• ChemBase ID: 158631
• Molecular Formular: C21H22N2O5S
• Molecular Mass: 414.47478
• Monoisotopic Mass: 414.12494281
• SMILES: CCOC(=O)COc1cc2ccc(nc2c(c1)NS(=O)(=O)c1ccc(cc1)C)C
• Canonical SMILES: CCOC(=O)COc1cc(NS(=O)(=O)c2ccc(cc2)C)c2c(c1)ccc(n2)C
• InChI: InChI=1S/C21H22N2O5S/c1-4-27-20(24)13-28-17-11-16-8-7-15(3)22-21(16)19(12-17)23-29(25,26)18-9-5-14(2)6-10-18/h5-12,23H,4,13H2,1-3H3
• InChIKey: KCASTCXJTDRDFT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-{[2-methyl-8-(4-methylbenzenesulfonamido)quinolin-6-yl]oxy}acetate
• IUPAC Traditional name: ethyl 2-{[2-methyl-8-(4-methylbenzenesulfonamido)quinolin-6-yl]oxy}acetate
• Synonyms: Ethyl [2-methyl-8-[[(4-methylphenyl)sulfonyl]amino]-6-quinolinyl]oxy Acetate; Zinquin Ethyl Ester; 2-Methyl-8-[(4-methylphenyl)sulfonylamino]-6-(ethyloxycarbonylmethyloxy)quinoline; Zinquin ethyl ester

Database IDs

• CAS Number: 181530-09-6
• MDL Number: MFCD00797629
• PubChem SID: 162252767
• PubChem CID: 3638243

CALCULATED PROPERTIES

• Acid pKa: 6.9908204
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.0378528
• LogD (pH = 7.4): 2.6391242
• Log P: 3.0863714
• Molar Refractivity: 108.5097 cm^3
• Polarizability: 44.136864 Å^3
• Polar Surface Area: 94.59 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichlormethane; DMSO; DMSO: soluble; Ethanol; methanol: soluble
• Apperance: off-white solid; White or Pale Blue Crystalline Solid
• Melting Point: 112-114°C

Safety Information

• Storage Warning: Temperature Sensitive; Store at -20°C
• 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: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C21H22N2O5S

DETAILS

Sigma Aldrich - Z2251

Biochem/physiol Actions
Used to detect zinc in cells by UV fluorescence.

Toronto Research Chemicals - Z450000

A fluorescent reagent and indicator of intracellular zinc ions. An analogue of widely used indicator, TS-Q. Zinquin ethyl ester is membrane permeable therefore useful to detect intracellular zinc ions. Zinquin ethyl ester forms a complex with a zinc ion

REFERENCES

• Zalewski, P.D., et al.: Biochem.J., 296, 403 (1993)
• Zalewski, P.D., et al.: J. Histochem. Cytochem., 42, 877 (1993)
• Zalewski, P.D., et al.: Biochem.J., 303, 278 (1993)
• Zalewski, P.D., et al.: Chemistry & Biology, 1, 153 (1994)