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Tenofovir disoproxil

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Identification
Molecular formula
C19H30N5O10P
CAS number
147127-20-6
IUPAC name
S-[2-[3-[[4-[[[5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethyl] 3-methylbut-2-enethioate
State
State

At room temperature, Tenofovir disoproxil is typically in the form of a solid powder. It is hygroscopic, meaning it can absorb moisture from the air, which is relevant for its storage and handling conditions.

Melting point (Celsius)
115.00
Melting point (Kelvin)
388.15
Boiling point (Celsius)
900.00
Boiling point (Kelvin)
1 173.15
General information
Molecular weight
519.46g/mol
Molar mass
519.4590g/mol
Density
1.4900g/cm3
Appearence

Tenofovir disoproxil typically appears as a white to off-white powder. It is crystalline in nature and has no significant odor. In medicinal formulations, it is often processed into tablet form for ease of administration.

Comment on solubility

Solubility Characteristics of S-[2-[3-[[4-[[[5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethyl] 3-methylbut-2-enethioate

The solubility of S-[2-[3-[[4-[[[5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethyl] 3-methylbut-2-enethioate (C19H30N5O10P) is influenced by its complex molecular structure which incorporates multiple functional groups such as phosphonate and amino moieties.

1. **Polar and Ionic Influence**: The presence of phosphate groups and the amino functional groups typically enhance the polarity of the compound, suggesting potential solubility in polar solvents like water.
2. **Hydrogen Bonding**: Due to the presence of hydroxyl groups (–OH), the ability to participate in hydrogen bonding can significantly increase solubility. Thus, this compound may exhibit good solubility in aqueous environments.
3. **Solvent Interactions**: Solubility may vary with organic solvents; for instance, it might be less soluble in non-polar solvents compared to polar solvents.
4. **pH Sensitivity**: Solubility could also depend on the pH of the solution, as ions may emerge or change state under varying acidic or basic conditions.

In summary, one could *expect* that this compound exhibits good solubility in polar solvents, particularly due to its polar functional groups, alongside a possible solubility variation in different pH environments. As with many bioactive compounds, experimental solubility data would be essential to confirm these predictions.

Interesting facts

Exploring S-[2-[3-[[4-[[[5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethyl] 3-methylbut-2-enethioate

This complex compound is a fascinating example of advanced organic chemistry, showcasing the intricate design of molecules with multiple functional groups. Here are some interesting facts about this compound:

  • Biological Relevance: The structure includes an aminopurine moiety, which is reminiscent of purine bases found in nucleic acids. This suggests potential roles in biological systems, possibly even as a signaling molecule or building block for more complex structures.
  • Phosphorylation: With multiple phosphonate groups present, the compound highlights the significance of phosphorylation in biochemical pathways. Phosphorylation is essential for regulating various cellular processes, including enzyme activity and signal transduction.
  • Synthetic Challenge: The synthesis of this compound is likely to be complex due to its multiple branches and functional groups. The ability to navigate this synthesis can provide chemists with valuable skills in synthesizing intricate organic molecules.
  • Potential Applications: Given its structural components, this compound may find applications in drug design, particularly in the fields of cancer therapy or antiviral treatments, where modifications of nucleobases have shown promise.
  • Chemical Diversity: The compound serves as a prime example of how small changes in molecular structure can lead to significant differences in chemical behavior and biological activity.

In summary, this compound is not just a mere collection of atoms; it is a testament to the complexity of organic chemistry and the potential it holds for future scientific advancements. As we continue to explore such compounds, we uncover not only their properties but also their hidden roles in nature and technology.

Synonyms
3-Methylcrotonyl CoA
.beta.-Methylcrotonyl CoA
.beta.-Methylcrotonyl coenzyme A
Coenzyme A, S-(3-methyl-2-butenoate)
S-[2-[3-[[4-[[[5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 3-methylbut-2-enethioate
S-(2-(3-((4-(((5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl)methoxy-hydroxyphosphoryl)oxy-hydroxyphosphoryl)oxy-2-hydroxy-3,3-dimethylbutanoyl)amino)propanoylamino)ethyl) 3-methylbut-2-enethioate
beta-Methylcrotonyl CoA
SCHEMBL16018847
6712-03-4