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Camptothecin

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Identification
Molecular formula
C20H16N2O4
CAS number
7689-03-4
IUPAC name
[(2R,3R,5S,8R,10R,17S)-8-acetoxy-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
State
State

At room temperature, Camptothecin is solid.

Melting point (Celsius)
264.00
Melting point (Kelvin)
537.15
Boiling point (Celsius)
540.00
Boiling point (Kelvin)
813.15
General information
Molecular weight
348.35g/mol
Molar mass
348.3530g/mol
Density
1.4320g/cm3
Appearence

Camptothecin is typically a pale yellow crystalline powder.

Comment on solubility

Solubility of the Compound

The solubility of the compound [(2R,3R,5S,8R,10R,17S)-8-acetoxy-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate is influenced by several factors:

  • Polarity: The presence of multiple hydroxyl groups (-OH) and methoxy groups (-OCH3) makes the compound relatively polar, which can enhance its solubility in polar solvents.
  • Hydrogen Bonding: The ability of hydroxyl groups to form hydrogen bonds can significantly impact solubility. Increased hydrogen bonding interactions with solvent molecules can facilitate dissolution.
  • Hydrophobic Domain: The hexacyclic structure and non-polar segments may lead to limited solubility in water but can demonstrate better solubility in organic solvents.
  • Temperature: Generally, higher temperatures can increase solubility as kinetic energy allows for more interactions between solute and solvent.

In summary, while this compound may exhibit good solubility in polar solvents due to its functional groups, it may have challenges dissolving in less polar environments. The intricate balance of hydrophilic and hydrophobic characteristics underscores the compound's unique solubility profile.

Interesting facts

Interesting Facts about the Compound

This uniquely complex organic compound is a fascinating example in the realm of natural products and organic chemistry. Its structure is characterized by a variety of functional groups and stereoisomerism that plays a crucial role in its biological activity.

Key Highlights:

  • Complex Structure: The compound features a hexacyclic framework, incorporating multiple rings that add to its structural intricacy. This complexity is often a hallmark of many bioactive natural products.
  • Stereochemistry: Notably designated by multiple chiral centers, the R and S configurations are critical for determining the compound’s three-dimensional shape, significantly impacting its interactions with biological targets.
  • Natural Origin: Compounds similar to this one are frequently found in nature, particularly in plants, where they often serve defensive roles or play part in plant signaling pathways.
  • Potential Therapeutic Uses: Due to its diverse functional groups, it may exhibit a range of biological activities, including anti-inflammatory and anticancer properties, making it a candidate for medicinal chemistry research.

Researchers emphasize the importance of such compounds, stating, "The complexity of natural products continues to challenge chemists, but it is precisely this complexity that provides opportunities for the discovery of novel therapies." Thus, this compound not only embodies the intricate artistry of nature’s chemistry but also inspires ongoing research into its potential benefits.

Research Implications:

The study of this compound encourages:

  • A deeper understanding of structure-activity relationships.
  • Exploration of synthetic pathways to create analogs for enhanced efficacy.
  • Investigation of biochemical mechanisms mediated by its unique stereochemistry.

As we explore such compounds, we uncover the layers of chemical interactions that govern life, showcasing how chemistry not only describes but actively shapes biological functionalities.