ethyl 4-chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

• ChemBase ID: 80286
• Molecular Formular: C13H12ClNO3
• Molecular Mass: 265.69228
• Monoisotopic Mass: 265.05057093
• SMILES: n1(c(=O)c(c(c2ccccc12)Cl)C(=O)OCC)C
• Canonical SMILES: CCOC(=O)c1c(Cl)c2ccccc2n(c1=O)C
• InChI: InChI=1S/C13H12ClNO3/c1-3-18-13(17)10-11(14)8-6-4-5-7-9(8)15(2)12(10)16/h4-7H,3H2,1-2H3
• InChIKey: XUJQDJGGHFNYDY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate
• IUPAC Traditional name: ethyl 4-chloro-1-methyl-2-oxoquinoline-3-carboxylate
• Synonyms: 4-Chloro-1,2-dihydro-3-(ethoxycarbonyl)-1-methyl-2-oxoquinoline; 4-Chloro-3-(ethoxycarbonyl)-1-methylquinolin-2(1H)-one; Ethyl 4-chloro-1,2-dihydro-1-methyl-2-oxoquinoline-3-carboxylate; ethyl 4-chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate; 4-Chloro-1,2-dihydro-1-methyl-2-oxo-3-quinolinecarboxylic acid ethyl ester; Ethyl 4-chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate; AI-1

Database IDs

• CAS Number: 75483-04-4
• MDL Number: MFCD00634787
• PubChem SID: 162067406
• PubChem CID: 606180

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.93855
• LogD (pH = 7.4): 1.93855
• Log P: 1.93855
• Molar Refractivity: 68.7033 cm^3
• Polarizability: 26.15461 Å^3
• Polar Surface Area: 46.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥15 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Warning: Irritant/Air Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C13H12ClNO3

DETAILS

Sigma Aldrich - SML0009

Biochem/physiol Actions
AI-1 promotes Nrf2 activation via the covalent modification of Kelch-like ECH-associated protein 1 (Keap1), a negative regulator of Nrf2. Biochemical studies indicate that an aromatic chloride present within the AI-1 molecule undergoes a nucleophilic aromatic substitution reaction with cysteine thiols of Keap1.