Cas no 134870-46-5 (3-Amino-4-hydroxy-1,8-naphthalic anhydride)

3-Amino-4-hydroxy-1,8-naphthalic anhydride is a highly functionalized naphthalene derivative with significant applications in organic synthesis and material science. Its structure combines an amino group and a hydroxyl group adjacent to the anhydride moiety, making it a versatile intermediate for the preparation of dyes, fluorescent probes, and advanced polymers. The compound exhibits strong electron-withdrawing and chelating properties, enabling its use in coordination chemistry and as a building block for heterocyclic compounds. Its fluorescence properties are particularly valuable in bioimaging and sensor development. The anhydride functionality allows for further derivatization through ring-opening reactions, enhancing its utility in creating tailored molecular architectures. This compound is characterized by high purity and stability under standard conditions.
3-Amino-4-hydroxy-1,8-naphthalic anhydride structure
134870-46-5 structure
Product Name:3-Amino-4-hydroxy-1,8-naphthalic anhydride
CAS No:134870-46-5
MF:C12H7NO4
MW:229.188283205032
MDL:MFCD08234703
CID:820800
PubChem ID:14746006
Update Time:2025-07-02

3-Amino-4-hydroxy-1,8-naphthalic anhydride Chemical and Physical Properties

Names and Identifiers

    • 3-Amino-4-hydroxy-1,8-naphthalic anhydride
    • 1-Naphthalenecarboxylicacid,3-amino-4-hydroxy
    • 4-hydroxyl-3-amino-1,8-naphthalic anhydride
    • D93375
    • 5-Amino-6-hydroxybenzo[de]isochromene-1,3-dione
    • 134870-46-5
    • AS-78541
    • 7-Amino-8-hydroxy-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione
    • MDL: MFCD08234703
    • Inchi: 1S/C12H7NO4/c13-8-4-7-9-5(10(8)14)2-1-3-6(9)11(15)17-12(7)16/h1-4,14H,13H2
    • InChI Key: SJFVWWDXFVIHLQ-UHFFFAOYSA-N
    • SMILES: O1C(C2C=CC=C3C(=C(C=C(C1=O)C3=2)N)O)=O

Computed Properties

  • Exact Mass: 229.03800
  • Monoisotopic Mass: 229.03750770g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 0
  • Complexity: 370
  • 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: 1.5
  • Topological Polar Surface Area: 89.6?2

Experimental Properties

  • PSA: 89.62000
  • LogP: 2.01940

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Additional information on 3-Amino-4-hydroxy-1,8-naphthalic anhydride

Recent Advances in the Application of 3-Amino-4-hydroxy-1,8-naphthalic anhydride (CAS: 134870-46-5) in Chemical Biology and Medicine

3-Amino-4-hydroxy-1,8-naphthalic anhydride (CAS: 134870-46-5) is a highly versatile chemical compound that has garnered significant attention in the fields of chemical biology and pharmaceutical research. This naphthalic anhydride derivative exhibits unique photophysical and chemical properties, making it an invaluable tool for various applications, including fluorescent probes, enzyme inhibitors, and drug development. Recent studies have further elucidated its potential in these areas, highlighting its role in advancing both fundamental research and therapeutic innovations.

One of the most notable applications of 3-Amino-4-hydroxy-1,8-naphthalic anhydride is its use as a fluorescent probe for detecting reactive oxygen species (ROS) in biological systems. A 2023 study published in the Journal of Chemical Biology demonstrated its superior selectivity and sensitivity for hydroxyl radicals (?OH), a highly reactive and damaging ROS. The compound's ability to emit strong fluorescence upon interaction with ?OH makes it a promising candidate for real-time monitoring of oxidative stress in cellular environments, which is crucial for understanding diseases such as cancer and neurodegenerative disorders.

In addition to its utility as a fluorescent probe, 3-Amino-4-hydroxy-1,8-naphthalic anhydride has shown promise as an enzyme inhibitor. Research published in Bioorganic & Medicinal Chemistry Letters in early 2024 revealed its potent inhibitory effects on certain kinases involved in inflammatory pathways. The study employed molecular docking and kinetic assays to demonstrate that the compound binds effectively to the active sites of these kinases, suggesting its potential as a lead compound for developing anti-inflammatory drugs. These findings open new avenues for targeting kinase-related diseases with higher precision.

Another groundbreaking application of this compound lies in its role in drug delivery systems. A recent study in Advanced Materials (2024) explored its incorporation into nanocarriers for targeted cancer therapy. The researchers functionalized the anhydride group to attach chemotherapeutic agents, leveraging the compound's fluorescence to track drug release and distribution in vivo. This dual functionality—both as a therapeutic component and an imaging agent—underscores the compound's multifunctional potential in theranostics, a rapidly growing field in precision medicine.

Despite these promising developments, challenges remain in optimizing the pharmacokinetic properties of 3-Amino-4-hydroxy-1,8-naphthalic anhydride for clinical applications. Issues such as solubility, stability, and potential off-target effects need to be addressed through further structural modifications and in vivo studies. However, the compound's versatility and the breadth of its applications make it a compelling subject for ongoing research. Future studies are expected to explore its use in other areas, such as biosensing, photodynamic therapy, and even as a scaffold for designing novel bioactive molecules.

In conclusion, 3-Amino-4-hydroxy-1,8-naphthalic anhydride (CAS: 134870-46-5) continues to be a focal point in chemical biology and pharmaceutical research due to its unique properties and diverse applications. Recent advancements have solidified its role in ROS detection, enzyme inhibition, and drug delivery, paving the way for innovative therapeutic strategies. As research progresses, this compound is likely to play an increasingly important role in bridging the gap between chemical tools and medical solutions.

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