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Acridine Orange

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Identification
Molecular formula
C17H19N3
CAS number
494-38-2
IUPAC name
9,9-dimethyl-10-[3-(4-pyrrolidin-1-ium-1-ylpiperidin-1-ium-1-yl)propyl]acridine;4-hydroxy-4-oxo-but-2-enoate
State
State

At room temperature, Acridine Orange exists as a solid.

Melting point (Celsius)
267.00
Melting point (Kelvin)
540.15
Boiling point (Celsius)
325.00
Boiling point (Kelvin)
598.15
General information
Molecular weight
265.33g/mol
Molar mass
265.3340g/mol
Density
1.1500g/cm3
Appearence

Acridine Orange is an organic compound that appears as an orange or yellowish powder. It has a crystalline structure and exhibits bright green fluorescence when exposed to UV light. This compound is often used as a fluorescent dye in a variety of biological applications due to its ability to intercalate with nucleic acids.

Comment on solubility

Solubility of 9,9-Dimethyl-10-[3-(4-pyrrolidin-1-ium-1-ylpiperidin-1-ium-1-yl)propyl]acridine; 4-hydroxy-4-oxo-but-2-enoate

This compound, with its complex structure containing multiple functional groups, exhibits intriguing solubility characteristics. The solubility of such a molecule can typically be influenced by the following factors:

  • Polarity: The presence of charged (pyrrolidin-1-ium and piperidin-1-ium) and polar functional groups enhances its solubility in polar solvents, such as water and certain alcohols.
  • Hydrogen bonding: The hydroxyl group in the 4-hydroxy-4-oxo-but-2-enoate portion of the molecule can participate in hydrogen bonding, potentially increasing solubility in protic solvents.
  • Hydrophilicity vs. Hydrophobicity: The balance between hydrophilic (water-attracting) and hydrophobic (water-repelling) portions of the molecule determines overall solubility. The acridine moiety is relatively hydrophobic, which may limit solubility in aqueous environments.
  • Temperature: Increased temperature generally improves solubility. For example, "as temperature rises, solubility often increases," enabling better interactions with solvent molecules.

In summary, while the charged and polar nature of portions of this compound may enhance solubility in aqueous or polar environments, the hydrophobic characteristics of some structural units might restrict its complete solubility profile. Understanding these interactions is crucial for predicting behavior in various solvents.

Interesting facts

Interesting Facts about 9,9-Dimethyl-10-[3-(4-pyrrolidin-1-ium-1-ylpiperidin-1-ium-1-yl)propyl]acridine; 4-hydroxy-4-oxo-but-2-enoate

This fascinating compound embodies a remarkable intersection of organic chemistry and pharmacological potential due to its complex structure and functional groups. Here are some engaging facts about it:

  • Structural Complexity: The structure features a unique combination of acridine and pyrrolidine groups, leading to interesting interactions with biological systems.
  • Potential Applications: Given its structural components, this compound could have applications in medicinal chemistry, particularly in the development of new drugs targeting neurological disorders.
  • Charge Dynamics: The presence of quaternary ammonium groups contributes to its charge properties, which can enhance solubility in biological environments and increase its potential as a drug candidate.
  • Synthesis Challenges: Creating this compound requires advanced synthetic techniques, making it an interesting case study for chemists focusing on multi-step synthesis.
  • Mechanistic Studies: Researchers are intrigued by exploring how this compound interacts at a molecular level, providing insights into receptor binding and signaling pathways.

"Understanding the intricate details of compounds like this one can unlock new pathways in drug discovery and design."

This compound represents a significant achievement in synthetic chemistry and depicts the potential of complex molecules in therapeutics, inviting ongoing exploration and study by scientists worldwide.