Cas no 26892-90-0 (Ethyl 4-hydroxyquinoline-3-carboxylate)

Ethyl 4-hydroxyquinoline-3-carboxylate is a versatile heterocyclic compound featuring a quinoline core substituted with a hydroxyl group at the 4-position and an ester moiety at the 3-position. This structure imparts reactivity suitable for applications in pharmaceutical intermediates, organic synthesis, and coordination chemistry. The compound serves as a valuable precursor for synthesizing biologically active molecules, including antimicrobial and antitumor agents. Its ester functionality allows for further derivatization, while the hydroxyl group enhances solubility and participation in hydrogen bonding. Ethyl 4-hydroxyquinoline-3-carboxylate exhibits stability under standard conditions, facilitating handling and storage. Its balanced reactivity and structural features make it a useful building block in medicinal chemistry and material science research.
Ethyl 4-hydroxyquinoline-3-carboxylate structure
26892-90-0 structure
Product Name:Ethyl 4-hydroxyquinoline-3-carboxylate
CAS No:26892-90-0
MF:C12H11NO3
MW:217.220643281937
MDL:MFCD00173406
CID:288775
PubChem ID:253661311
Update Time:2025-10-18

Ethyl 4-hydroxyquinoline-3-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Ethyl 4-hydroxyquinoline-3-carboxylate
    • 4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
    • 4-keto-1H-quinoline-3-carboxylic acid ethyl ester
    • ethyl 4-oxo-1H-quinoline-3-carboxylate
    • 3-Quinolinecarboxylic acid, 4-hydroxy-, ethyl ester
    • 3-CHLORO-7-BROMO-4-HYDROXYQUINOLINE
    • Ethyl 4-oxo-1,4-dihydro-3-quinolinecarboxylate
    • 4-Hydroxy-3-Quinolinecarboxylicacid Ethyl Ester
    • 4-hydroxy-quinoline-3-carboxy
    • 4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
    • NSC 4345
    • Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate
    • 3-Quinolinecarboxylic acid, 1,4-dihydro-4-oxo-, ethyl ester
    • ethyl 1,4-dihydro-4-oxoquinoline-3-carboxylate
    • ethyl 4-oxohydroquinoline-3-carboxylate
    • 4-HYDROXY-QUINOLINE-3-CARBOXYLIC ACID METHYL ESTER
    • 4-Oxo-1,4-dihydro-quinoline-3-carboxylic acid
    • 4-Hydroxyquinoline-3-carboxylic acid ethyl ester 98%
    • 4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER, 95+%
    • 3-Ethoxycarbonyl-4-quinolinol
    • 52980-28-6
    • C69YF4B94W
    • AC-2909
    • BDBM50597207
    • EN300-216558
    • Oprea1_431187
    • HMS1364H19
    • J-650308
    • Z1117775570
    • Bionet2_000173
    • 1H-quinolin-4-one-3-carboxylic acid ethyl ester
    • SY003321
    • 4-Hydroxy-quinoline-3-carboxylic acid ethyl ester
    • 3-carbethoxy-4-hydroxy-quinoline
    • F0777-1766
    • SR-01000389825-2
    • 4-Hydroxy-quinoline-3-carboxylic acid ethyl ester
    • FT-0638645
    • Ethyl 4-hydroxy-1,4-dihydroquinoline-3-carboxylate
    • AM803611
    • 4-Hydroxyquinoline-3-carboxylic acid ethyl ester, AldrichCPR
    • SR-01000389825
    • NSC-4345
    • UNII-C69YF4B94W
    • FT-0680504
    • F0347-1822
    • Ethyl 4-hydroxy-3-quinolinecarboxylate
    • ethyl 1,4-dihydro-4-oxo-3-quinolinecarboxylate
    • AKOS000538997
    • A818657
    • CHEMBL382363
    • InChI=1/C12H11NO3/c1-2-16-12(15)9-7-13-10-6-4-3-5-8(10)11(9)14/h3-7H,2H2,1H3,(H,13,14
    • SCHEMBL376662
    • SY076061
    • Ethyl 4-hydroxy-quinoline-3-carboxylate
    • Ethyl 4-oxo-1,4-dihydro-3-quinolinecarboxylate #
    • EC 695-104-1
    • Maybridge1_006707
    • NS00008653
    • SB71446
    • NSC4345
    • J-520510
    • AC-907/25005192
    • SR-01000389825-1
    • AB04345
    • HMS560I19
    • BRD-K63122470-001-01-0
    • ethyl-4-hydroxyquinoline-3-carboxylate
    • 26892-90-0
    • CCG-126720
    • [(2E)-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl)prop-2-enyl]dimethylamine hydrochloride
    • MFCD01314279
    • CS-M2628
    • 3-carboethoxy-1,4-dihydro-4-oxoquinoline
    • DTXSID10277822
    • Oprea1_405827
    • BB 0221685
    • 6J-050
    • PD181376
    • Ethyl4-oxo-1,4-dihydroquinoline-3-carboxylate
    • J-521013
    • CCG-51391
    • MFCD00173406
    • E1142
    • 3-Quinolinecarboxylicacid,4-hydroxy-,ethyl ester
    • Oprea1_770092
    • ethyl 4-hydroxy-3-quinoline-carboxylate
    • AKOS000275121
    • 1,4-Dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester
    • STK945052
    • ALBB-011548
    • 3-Ethoxycarbonyl-4(1H)-quinolone; 4-Oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester; Ethyl 1,4-dihydro-4-oxoquinoline-3-carboxylate; Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate;
    • DB-047042
    • MDL： MFCD00173406
    • Inchi： 1S/C12H11NO3/c1-2-16-12(15)9-7-13-10-6-4-3-5-8(10)11(9)14/h3-7H,2H2,1H3,(H,13,14)
    • InChI Key： YBEOYBKKSWUSBR-UHFFFAOYSA-N
    • SMILES： O(CC)C(C1=CNC2C=CC=CC=2C1=O)=O

Computed Properties

  • Exact Mass: 217.07400
  • Monoisotopic Mass: 217.07389321g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 335
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 55.4
  • XLogP3: 2

Experimental Properties

  • Color/Form: No data available
  • Density: 1.280±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 271°C(lit.)
  • Boiling Point: 343.7℃ at 760 mmHg
  • Flash Point: 161.7℃
  • Solubility: Very slightly soluble (0.54 g/l) (25 o C),
  • PSA: 59.42000
  • LogP: 2.11710
  • pka: 2.62±0.50(Predicted)

Ethyl 4-hydroxyquinoline-3-carboxylate Security Information

Ethyl 4-hydroxyquinoline-3-carboxylate Customs Data

  • HS CODE：2933499090

Ethyl 4-hydroxyquinoline-3-carboxylate Pricemore >>

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Ethyl 4-hydroxyquinoline-3-carboxylate Production Method

Ethyl 4-hydroxyquinoline-3-carboxylate Related Literature

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Additional information on Ethyl 4-hydroxyquinoline-3-carboxylate

Recent Advances in the Research of Ethyl 4-hydroxyquinoline-3-carboxylate (CAS: 26892-90-0)

Ethyl 4-hydroxyquinoline-3-carboxylate (CAS: 26892-90-0) is a quinoline derivative that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its versatile pharmacological properties. Recent studies have explored its potential as a key scaffold in the development of novel therapeutic agents, particularly in the areas of anti-inflammatory, antimicrobial, and anticancer research. This research brief aims to summarize the latest findings and advancements related to this compound, providing a comprehensive overview of its applications and mechanisms of action.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers investigated the anti-inflammatory effects of Ethyl 4-hydroxyquinoline-3-carboxylate. The study demonstrated that the compound effectively inhibits the production of pro-inflammatory cytokines such as TNF-α and IL-6 in macrophage cells, suggesting its potential as a therapeutic agent for inflammatory diseases. The mechanism of action was attributed to the compound's ability to modulate the NF-κB signaling pathway, a critical regulator of inflammation.

Another significant advancement was reported in a 2022 paper in Bioorganic & Medicinal Chemistry Letters, where Ethyl 4-hydroxyquinoline-3-carboxylate was evaluated for its antimicrobial activity against a panel of drug-resistant bacterial strains. The results indicated that the compound exhibited potent activity against methicillin-resistant Staphylococcus aureus (MRSA) and extended-spectrum β-lactamase (ESBL)-producing Escherichia coli. The study highlighted the compound's potential as a lead structure for the development of new antibiotics to address the growing challenge of antimicrobial resistance.

Recent research has also explored the anticancer properties of Ethyl 4-hydroxyquinoline-3-carboxylate. A 2023 study in European Journal of Medicinal Chemistry revealed that the compound induces apoptosis in human breast cancer cells (MCF-7) through the activation of the intrinsic apoptotic pathway. The study further identified that the compound's efficacy is enhanced when combined with conventional chemotherapeutic agents, suggesting its potential as an adjunct therapy in cancer treatment.

In addition to its pharmacological applications, Ethyl 4-hydroxyquinoline-3-carboxylate has been investigated for its role in chemical biology. A 2021 study in Chemical Communications demonstrated its utility as a fluorescent probe for detecting metal ions in biological systems. The compound's unique photophysical properties make it a promising tool for imaging and diagnostic applications.

In conclusion, Ethyl 4-hydroxyquinoline-3-carboxylate (CAS: 26892-90-0) continues to be a compound of significant interest in chemical biology and medicinal chemistry. Its diverse pharmacological activities, coupled with its potential as a scaffold for drug development, underscore its importance in ongoing research efforts. Future studies are expected to further elucidate its mechanisms of action and explore its applications in novel therapeutic strategies.

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