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Cyclosporin A

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Identification
Molecular formula
C62H111N11O12
CAS number
59865-13-3
IUPAC name
4-[[3-amino-2-[[2-[[2-[(2,3-dihydroxy-2,6,8-trimethyl-deca-4,6-dienoyl)amino]acetyl]amino]-3-hydroxy-butanoyl]amino]butanoyl]amino]-N'-[6-(1-hydroxyethyl)-3-[(4-hydroxyphenyl)-methoxy-methyl]-19-isopropyl-15-(methoxymethyl)-7,9-dimethyl-2,5,8,11,14,17,21-heptaoxo-20-oxa-1,4,7,10,13,16-hexazabicyclo[20.4.0]hexacosan-18-yl]-2,3-dimethyl-pentanediamide
State
State

Cyclosporin A is a solid at room temperature. It is stable under standard conditions and typically provided as a microemulsion for pharmaceutical preparations.

Melting point (Celsius)
148.00
Melting point (Kelvin)
421.15
Boiling point (Celsius)
785.15
Boiling point (Kelvin)
1 058.30
General information
Molecular weight
1202.61g/mol
Molar mass
1 202.6100g/mol
Density
1.0800g/cm3
Appearence

Cyclosporin A is a cyclic undecapeptide consisting of 11 amino acids. It appears as a white to almost white powder or crystalline solid, depending on the degree of hydration and purity. It is practically insoluble in water and freely soluble in organic solvents such as alcohols and chloroform.

Comment on solubility

Solubility of 4-[[3-amino-2-[[2-[[2-[(2,3-dihydroxy-2,6,8-trimethyl-deca-4,6-dienoyl)amino]acetyl]amino]-3-hydroxy-butanoyl]amino]butanoyl]amino]-N'-[6-(1-hydroxyethyl)-3-[(4-hydroxyphenyl)-methoxy-methyl]-19-isopropyl-15-(methoxymethyl)-7,9-dimethyl-2,5,8,11,14,17,21-heptaoxo-20-oxa-1,4,7,10,13,16-hexazabicyclo[20.4.0]hexacosan-18-yl]-2,3-dimethyl-pentanediamide

The solubility of complex organic compounds such as 4-[[3-amino-2-[[2-[[2-[(2,3-dihydroxy-2,6,8-trimethyl-deca-4,6-dienoyl)amino]acetyl]amino]-3-hydroxy-butanoyl]amino]butanoyl]amino]-N'-[6-(1-hydroxyethyl)-3-[(4-hydroxyphenyl)-methoxy-methyl]-19-isopropyl-15-(methoxymethyl)-7,9-dimethyl-2,5,8,11,14,17,21-heptaoxo-20-oxa-1,4,7,10,13,16-hexazabicyclo[20.4.0]hexacosan-18-yl]-2,3-dimethyl-pentanediamide (C62H111N11O12) is a multifaceted subject.

Some key points to consider include:

  • Hydrophilicity vs. Hydrophobicity: The presence of polar functional groups may enhance the solubility in aqueous environments, whereas the hydrophobic regions can lead to limited solubility.
  • Molecular Weight: The high molecular weight of this compound could contribute to decreased solubility compared to smaller molecules.
  • Interactions with Solvents: Depending on the solvent used—whether it's water or an organic solvent—the solubility profile may drastically differ.
  • Temperature and pH Effects: Solubility can be influenced by changes in temperature and the acidity or basicity of the solution, potentially altering the compound’s behavior.

In conclusion, predicting the solubility of this intricate compound requires consideration of various physical and chemical factors. As noted, "the behavior of a compound in solution can often be as complex as the structure itself." Understanding these aspects is crucial for applications in pharmaceuticals and material sciences.

Interesting facts

Interesting Facts About 4-[[3-amino-2-[[2-[[2-[(2,3-dihydroxy-2,6,8-trimethyl-deca-4,6-dienoyl)amino]acetyl]amino]-3-hydroxy-butanoyl]amino]butanoyl]amino]-N'-[6-(1-hydroxyethyl)-3-[(4-hydroxyphenyl)-methoxy-methyl]-19-isopropyl-15-(methoxymethyl)-7,9-dimethyl-2,5,8,11,14,17,21-heptaoxo-20-oxa-1,4,7,10,13,16-hexazabicyclo[20.4.0]hexacosan-18-yl]-2,3-dimethyl-pentanediamide

This compound is a complex, multifunctional organic molecule that highlights the marvels of modern organic chemistry. Its intricate structure serves multiple purposes—including as a potential agent in therapeutic applications.

Key Highlights:

  • Structural Complexity: The molecule features a myriad of amine groups and modifications that contribute to its unique physical and chemical properties.
  • Bioactivity: Compounds with similar structures have been explored for biological activities, potentially acting as targets for drug development, especially in the field of cancer research.
  • Natural Inspirations: The extensive presence of hydroxyl and methoxy groups often reflects modifications found in naturally occurring compounds, such as flavonoids and alkaloids, which enhance their reactivity and interaction with biological systems.
  • Molecular Recognition: The inclusion of hydrophobic trap-like frameworks could facilitate molecular recognition processes, enhancing the compound's ability to bind specifically with biological macromolecules.

In the field of medicinal chemistry, the design and synthesis of such compounds often lead to the discovery of novel therapeutic agents. As one researcher stated, "The beauty of organic synthesis lies not just in the products but also in the potential they unlock for new therapies." Through the study of this compound, scientists can gain insights into structure-activity relationships (SAR), which are crucial in drug discovery.

Overall, this complex molecule stands as a testament to the creativity and ingenuity inherent in chemical research, prompting ongoing investigations into its potential applications in health sciences.