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Paclitaxel

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Identification
Molecular formula
C47H51NO14
CAS number
33069-62-4
IUPAC name
[3-[5-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-3-hydroxy-6-methyl-4-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] 3-[6-[3,4-dihydroxy-5-[6-hydroxy-2-(hydroxymethyl)-6-methyl-octa-2,7-dienoyl]oxy-6-methyl-tetrahydropyran-2-yl]oxy-2-(hydroxymethyl)-6-methyl-octa-2,7-dienoyl]oxy-10-[6-[[4,5-dihydroxy-6-methyl-3-(3,4,5-trihydroxytetrahydropyran-2-yl)oxy-tetrahydropyran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
State
State

Paclitaxel is a solid at room temperature.

Melting point (Celsius)
217.00
Melting point (Kelvin)
490.15
Boiling point (Celsius)
499.85
Boiling point (Kelvin)
773.00
General information
Molecular weight
853.91g/mol
Molar mass
853.9060g/mol
Density
1.3800g/cm3
Appearence

Paclitaxel appears as a white or almost white crystalline powder.

Comment on solubility

Solubility of the Compound

The solubility of this complex compound, identified as 3-[5-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-3-hydroxy-6-methyl-4-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl] 3-[6-[3,4-dihydroxy-5-[6-hydroxy-2-(hydroxymethyl)-6-methyl-octa-2,7-dienoyl]oxy-6-methyl-tetrahydropyran-2-yl]oxy-2-(hydroxymethyl)-6-methyl-octa-2,7-dienoyl]oxy-10-[6-[[4,5-dihydroxy-6-methyl-3-(3,4,5-trihydroxytetrahydropyran-2-yl)oxy-tetrahydropyran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate (C47H51NO14) can be best understood in relation to its structural features.


Key points to consider regarding its solubility include:

  • Polarity: The presence of multiple hydroxyl groups (–OH) suggests a certain degree of polarity, potentially enhancing its solubility in polar solvents such as water.
  • Hydrophobic Regions: The compound also contains hydrophobic segments that may limit its overall solubility in aqueous solutions.
  • Hydrogen Bonding: The ability of hydroxyl groups to form hydrogen bonds can facilitate solubility interactions with water molecules.
  • Saturation: Given its complex structure, the solubility may be influenced by the saturation level of the compound.

In conclusion, while it is likely that this compound exhibits some degree of solubility in polar solvents due to its extensive hydroxyl functionality, the variation brought about by its hydrophobic regions could restrict its solubility. This leads to the statement that solubility is influenced by a balance between polar and nonpolar characteristics, making for an intriguing study in solvation chemistry.

Interesting facts

Interesting Facts about a Complex Organic Compound

This compound, with its extensive and intricate structure, presents a fascinating exploration within organic chemistry. As a tangle of various functional groups and unique stereochemical configurations, it serves as a prime example of the complexity achievable in organic synthesis. Here are some exceptional aspects about this compound:

  • Diversity in Functional Groups: The presence of multiple hydroxyl groups (-OH) and ether linkages showcases its ability to engage in hydrogen bonding and contribute to overall solubility in various solvents.
  • Applications in Natural Products: Compounds like this often exhibit biological activity and may be related to natural products such as flavonoids, affecting human health through antioxidant properties.
  • Synthetic Challenges: The synthesis of complex molecules like this is challenging and often requires multi-step procedures, protective group strategies, and high precision in stereochemistry.
  • Potential for Derivatization: The numerous functional groups provide opportunities for chemical modification, which can lead to new compounds with varied applications in pharmaceuticals or agrochemicals.

Moreover, such structural complexity can be an excellent subject for in-depth studies in fields like Medicinal Chemistry and Natural Product Chemistry, where understanding the mechanism of action helps in drug design. As one scientist remarked, "The study of complex organic compounds is like unraveling a mystery, revealing the secrets of nature one bond at a time."

Overall, this compound is not merely a chemical entity; it represents a bridge between basic research and practical applications, encouraging further inquiries and innovations in the chemical sciences.