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Paclitaxel

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Identification
Molecular formula
C47H51N3O14
CAS number
33069-62-4
IUPAC name
5-[(7,8-dihydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy]-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one
State
State

Solid: Paclitaxel is in solid state at room temperature and is typically presented as a crystalline powder.

Melting point (Celsius)
216.00
Melting point (Kelvin)
489.15
Boiling point (Celsius)
520.00
Boiling point (Kelvin)
793.15
General information
Molecular weight
853.91g/mol
Molar mass
853.9060g/mol
Density
1.7370g/cm3
Appearence

Paclitaxel is a white to off-white crystalline powder. It is not soluble in water, which affects its formulation and administration in pharmaceutical applications. When prepared for medical use, it is often formulated in a solution for intravenous injection.

Comment on solubility

Solubility Overview

The solubility of complex organic compounds like 5-[(7,8-dihydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy]-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one can be influenced by various factors. Understanding these factors is key to predicting the compound's behavior in different environments.

Key Factors Affecting Solubility

  • Polarity: The presence of hydroxyl (–OH) groups increases polarity, potentially enhancing solubility in polar solvents like water.
  • Functional Groups: The complex arrangement of methoxy (–OCH3) groups can lead to enhanced interactions with organic solvents.
  • Hydrogen Bonding: Intermolecular hydrogen bonding due to functional groups may significantly affect solubility.
  • Alkyl vs. Aromatic: With both aromatic and aliphatic components, the solubility may vary based on the solvent used.

Although the compound has the potential for solubility in organic solvents due to its numerous functional groups, its large and complex structure might limit solubility in polar solvents. As a result, one might observe a solubility pattern that reflects:

  1. Higher solubility in non-polar organic solvents.
  2. Limited solubility in water and other polar solvents.

In conclusion, the solubility of such intricate compounds is best approached with a combination of experimental data and theoretical predictions to ascertain the behavior in various solvents.

Interesting facts

Interesting Facts About 5-[(7,8-dihydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy]-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one

This complex compound, often referred to for its intricate structure and potential biological applications, is a fascinating example of organic chemistry's capability to create intricate molecular architectures. Here are some intriguing aspects worth noting:

  • Natural Product Inspiration: Many such compounds are derived from or inspired by natural products. They can exhibit biological activities such as antibacterial, antifungal, or antioxidant properties.
  • Multiple Functional Groups: The presence of several functional groups, including multiple methoxy (–OCH3) and hydroxyl (–OH) groups, suggests versatile reactivity, enabling the compound to engage in various chemical reactions.
  • Structural Complexity: Its structure includes not only a fused ring system but also variations in stereochemistry that could affect both its physical properties and how it interacts with biological systems.
  • Potential Applications: Due to its diverse structure, this compound may be studied for its potential use in pharmaceuticals, specifically in drug design aimed at targeting various diseases.
  • Chemical Synthesis Challenges: The synthesis of such a compound often poses challenges, making it an exciting area of research in synthetic organic chemistry.

As a chemistry student or enthusiast, one can appreciate the deep interconnections between molecular structure and function. Analyzing structures like this fuels the ongoing quest for new compounds that can improve human health, emphasizing the similar importance of both chemistry and biology in the development of therapies.

In the words of renowned chemist Robert H. Grubbs, “Chemistry is the art of building substances." This compound beautifully embodies that art, showcasing the incredible possibilities within the realm of organic chemistry.

Synonyms
Podophyllotoxin 1-O-beta-D-glycoside; Podophyllotoxin 4-O-glucoside; NSC 163024; Podophyllotoxin-4-O-beta-D-glucopyranoside