Skip to main content

Zidovudine

ADVERTISEMENT
Identification
Molecular formula
C10H13N5O4
CAS number
30516-87-1
IUPAC name
[(2R,3R,4S,5R)-3,4-diacetoxy-5-(4-amino-2-oxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate
State
State

At room temperature, zidovudine is in a solid state, specifically as a crystalline solid.

Melting point (Celsius)
123.00
Melting point (Kelvin)
396.15
Boiling point (Celsius)
350.00
Boiling point (Kelvin)
623.15
General information
Molecular weight
267.24g/mol
Molar mass
267.2420g/mol
Density
1.5200g/cm3
Appearence

Zidovudine appears as a white to off-white crystalline powder. It is hygroscopic and has a bitter taste. The compound is usually odorless.

Comment on solubility

Solubility Characteristics

The compound [(2R,3R,4S,5R)-3,4-diacetoxy-5-(4-amino-2-oxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate exhibits unique solubility properties influenced by its complex structure. When considering its solubility, the following points are noteworthy:

  • Polarity: The presence of multiple functional groups, such as acetoxy and amino groups, suggests that the compound may possess polar characteristics, potentially enhancing its solubility in polar solvents like water and ethanol.
  • Hydrogen Bonding: The amino group may facilitate hydrogen bonding with solvents, which enhances solubility, particularly in polar media.
  • Solvent Effects: This compound is expected to dissolve well in organic solvents, such as DMSO and methanol, while its solubility in nonpolar solvents like hexane may be markedly lower.
  • Temperature Dependency: As with many compounds, solubility can be temperature dependent. Increased temperatures often lead to higher solubility, making thermal management essential in practical applications.

Overall, the solubility of this compound can be described as being influenced by its functional groups and molecular interactions. As stated: "The solubility of a compound is crucial in determining its bioavailability and effectiveness in chemical applications."

Interesting facts

Exploring the Unique Compound: [(2R,3R,4S,5R)-3,4-diacetoxy-5-(4-amino-2-oxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate

This fascinating compound presents itself as a noteworthy example in the realm of organic chemistry, particularly due to its complex structure and potential applications. Here are some captivating details about this compound:

  • Multi-functional Role: The incorporation of pyrimidine rings within the structure underscores its potential as a pharmaceutical intermediate. Pyrimidines are a vital class of compounds known for their significance in the development of various medications, especially anticancer and antimicrobial agents.
  • Stereochemistry Matters: The specified stereochemical configuration (2R, 3R, 4S, 5R) illustrates the importance of chirality in drug design. Chirality can dramatically affect a compound’s biological activity, making thorough investigation vital for applications in pharmacology.
  • Acetoxy Groups: The presence of diacetoxy functional groups can enhance solubility and reactivity, paving the way for interesting pathways in synthetic chemistry. Acetylation is known to influence the biological activity of various compounds, which makes this feature particularly intriguing.
  • Synthetic Versatility: The tetrahydrofuran moiety offers a unique cyclic framework that often aids in the development of complex molecular architectures, showcasing the creativity inherent in synthetic organic chemistry.

As a compound of interest, [(2R,3R,4S,5R)-3,4-diacetoxy-5-(4-amino-2-oxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate exemplifies the intricate dance between structural complexity and functional application. This underscores the dynamic nature of chemical research, where each molecule carries the potential for groundbreaking discoveries.

Synonyms
Cytosine arabinoside triacetate
Tri-O-acetylarabinosylcytosine
NSC-93150
1-beta-D-Arabinofuranosylcytosine triacetate
1-beta-D-Arabinofuranosyl-2',3',5'-triacetate
1-beta-D-Arabinofuranosylcytosine, 2',3',5'-triacetate
Cytosine, 1beta-D-arabinofuranosyl-, 2',3',5'-triacetate
2(1H)-Pyrimidinone, 4-amino-1-(2,3,5-tri-O-acetyl-beta-D-arabinofuranosyl)-
CYTOSINE, 1-beta-D-ARABINO-FURANOSYL-, 2',3',5'-TRIACETATE
6742-07-0
2(1H)-Pyrimidinone, 4-amino-1-(2,3,5-tri-O-acetyl-beta-D-arabinofuranosyl)-(9CI)
Ara-C triacetate