9-Oxo-10(9H)-acridineacetic acid
[CAS# 38609-97-1]

Identification

• Classification: Analytical chemistry >> Analytical reagent >> Common analytical reagents
• Name: 9-Oxo-10(9H)-acridineacetic acid
• Synonyms: (9-Oxo-10(9H)-acridinyl)acetic acid
• Molecular Formula: C₁₅H₁₁NO₃
• Molecular Weight: 253.25
• CAS Registry Number: 38609-97-1
• EC Number: 634-833-1
• SMILES: C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3N2CC(=O)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.657, Calc.^*
• Boiling Point: 486.6±34.0 °C (760 mmHg), Calc.^*
• Flash Point: 248.1±25.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

9-Oxo-10(9H)-acridineacetic acid is an organic compound belonging to the class of acridine derivatives. It features a fused ring system composed of a heterocyclic acridine core with a carboxylic acid group at the acetic acid position. This compound has gained attention due to its interesting chemical structure and potential bioactive properties.

The discovery of 9-oxo-10(9H)-acridineacetic acid can be traced back to the mid-20th century when researchers began exploring acridine derivatives for their various biological activities, including antitumor and antimicrobial properties. Acridine-based compounds have a long history of being studied for their pharmacological effects, and 9-oxo-10(9H)-acridineacetic acid is one of the notable derivatives that emerged during these investigations. The compound is typically synthesized by introducing functional groups onto the acridine ring structure, often via oxidation or other reaction pathways to modify its reactivity and enhance its bioactivity.

One of the primary applications of 9-oxo-10(9H)-acridineacetic acid lies in the pharmaceutical and medicinal chemistry fields. Due to its structural resemblance to other biologically active acridine compounds, it has been investigated for its potential use as an anticancer agent. Acridine derivatives, including 9-oxo-10(9H)-acridineacetic acid, are known for their ability to intercalate DNA, inhibit topoisomerases, and disrupt cellular processes, making them candidates for cancer therapy. These compounds are particularly of interest in the development of novel chemotherapeutic agents that target cancer cells selectively while minimizing damage to healthy tissues.

Additionally, 9-oxo-10(9H)-acridineacetic acid has been studied for its potential antibacterial and antifungal properties. Acridine derivatives are known to exhibit antimicrobial activities, and the compound's structural characteristics contribute to its ability to interact with biological membranes and cellular components. This makes it a promising candidate for the development of new treatments for infections caused by resistant bacteria and fungi.

Beyond its pharmaceutical applications, 9-oxo-10(9H)-acridineacetic acid has also found use in material science. The compound’s fluorescent properties and its ability to form complexes with metal ions make it valuable in the development of novel materials for sensors and imaging technologies.

References

2021. STING, a promising target for small molecular immune modulator: A review. European Journal of Medicinal Chemistry, 211.
DOI: 10.1016/j.ejmech.2020.113113

1980. High-yield interferon induction by 10-carboxymethyl-9-acridanone in mice and hamsters. Antimicrobial Agents and Chemotherapy, 18(1).
DOI: 10.1128/aac.18.1.20