Cas no 5247-86-9 (methyl 8-hydroxynaphthalene-1-carboxylate)

methyl 8-hydroxynaphthalene-1-carboxylate structure
5247-86-9 structure
Product Name:methyl 8-hydroxynaphthalene-1-carboxylate
CAS No:5247-86-9
MF:C12H10O3
MW:202.206003665924
MDL:MFCD00665832
CID:936976
PubChem ID:608759
Update Time:2025-07-18

methyl 8-hydroxynaphthalene-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl 8-hydroxy-1-naphthoate
    • 8-hydroxy-naphthalene-1-carboxylic acid methyl ester
    • methyl 8-hydroxynaphthalene-1-carboxylate
    • DA-17850
    • CS-0043097
    • 5247-86-9
    • AKOS015919794
    • F15618
    • 8-hydroxynaphthalene-1-carboxylic acid methyl ester
    • DTXSID40346015
    • MFCD00665832
    • 8-Hydroxy-naphthoic acid, methyl ester
    • DSFFPEOQMHEQIH-UHFFFAOYSA-N
    • Methyl 8-hydroxy-1-naphthoate #
    • SCHEMBL3741831
    • PS-5857
    • MDL: MFCD00665832
    • Inchi: 1S/C12H10O3/c1-15-12(14)9-6-2-4-8-5-3-7-10(13)11(8)9/h2-7,13H,1H3
    • InChI Key: DSFFPEOQMHEQIH-UHFFFAOYSA-N
    • SMILES: OC1=CC=CC2=CC=CC(C(=O)OC)=C21

Computed Properties

  • Exact Mass: 202.063
  • Monoisotopic Mass: 202.062994177g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 239
  • 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
  • XLogP3: 2.7
  • Topological Polar Surface Area: 46.5?2

Experimental Properties

  • Density: 1.264±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 59-62 oC
  • Solubility: Very slightly soluble (0.28 g/l) (25 o C),
  • PSA: 46.53

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methyl 8-hydroxynaphthalene-1-carboxylate Production Method

Production Method 1

Reaction Conditions
1.1 Catalysts: Cytochrome CYP102 Solvents: Water ;  4 h, 37 °C
Reference
Bioconversion of substituted naphthalenes and β-eudesmol with the cytochrome P450 BM3 variant F87V
Misawa, Norihiko; Nodate, Miho; Otomatsu, Toshihiko; Shimizu, Keiko; Kaido, Chie; et al, Applied Microbiology and Biotechnology, 2011, 90(1), 147-157

methyl 8-hydroxynaphthalene-1-carboxylate Raw materials

methyl 8-hydroxynaphthalene-1-carboxylate Preparation Products

Additional information on methyl 8-hydroxynaphthalene-1-carboxylate

Research Brief on Methyl 8-Hydroxynaphthalene-1-Carboxylate (CAS: 5247-86-9): Recent Advances and Applications

Methyl 8-hydroxynaphthalene-1-carboxylate (CAS: 5247-86-9) is a naphthalene derivative that has garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications in drug discovery and material science. Recent studies have explored its potential as a building block for the synthesis of bioactive compounds, particularly in the development of novel therapeutic agents targeting inflammation, cancer, and infectious diseases. This research brief aims to summarize the latest findings related to this compound, highlighting its chemical properties, biological activities, and potential industrial applications.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers investigated the anti-inflammatory properties of methyl 8-hydroxynaphthalene-1-carboxylate and its derivatives. The study demonstrated that the compound exhibits potent inhibitory effects on key inflammatory mediators, such as cyclooxygenase-2 (COX-2) and tumor necrosis factor-alpha (TNF-α). These findings suggest its potential as a lead compound for the development of new anti-inflammatory drugs with improved efficacy and reduced side effects compared to existing therapeutics.

Another recent study, published in Bioorganic & Medicinal Chemistry Letters, explored the anticancer potential of methyl 8-hydroxynaphthalene-1-carboxylate. The researchers synthesized a series of analogs and evaluated their cytotoxicity against various cancer cell lines. The results indicated that certain derivatives exhibited selective toxicity toward cancer cells while sparing normal cells, highlighting the compound's potential as a scaffold for designing targeted anticancer agents. Mechanistic studies revealed that these derivatives induce apoptosis via the mitochondrial pathway, further supporting their therapeutic potential.

Beyond its pharmaceutical applications, methyl 8-hydroxynaphthalene-1-carboxylate has also been investigated for its utility in material science. A 2024 study in ACS Applied Materials & Interfaces reported the use of this compound as a precursor for the synthesis of organic semiconductors. The researchers demonstrated that its derivatives exhibit excellent charge transport properties, making them promising candidates for use in organic electronic devices such as light-emitting diodes (OLEDs) and photovoltaic cells.

In conclusion, methyl 8-hydroxynaphthalene-1-carboxylate (CAS: 5247-86-9) represents a versatile and valuable compound with broad applications in chemical biology and pharmaceutical research. Recent studies have underscored its potential as a therapeutic agent for inflammation and cancer, as well as its utility in material science. Future research should focus on optimizing its derivatives for enhanced bioactivity and exploring novel applications in other fields. The continued investigation of this compound is expected to yield significant advancements in drug discovery and material innovation.

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