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Uridine triacetate

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Identification
Molecular formula
C15H18N2O9
CAS number
4105-38-8
IUPAC name
[(2R,3R,4S,5R)-5-(4-acetamido-2-oxo-pyrimidin-1-yl)-3,4-diacetoxy-tetrahydrofuran-2-yl]methyl acetate
State
State

At room temperature, uridine triacetate is in a solid state. Its stable powdered form facilitates its handling, storage, and use in both clinical and research environments. The solid state ensures that it maintains its chemical integrity without the risk of evaporation or decomposition.

Melting point (Celsius)
196.00
Melting point (Kelvin)
469.15
Boiling point (Celsius)
245.00
Boiling point (Kelvin)
518.15
General information
Molecular weight
370.32g/mol
Molar mass
370.2770g/mol
Density
1.4908g/cm3
Appearence

Uridine triacetate is typically a white to off-white crystalline powder, presenting a fine and uniform texture. The compound's powder form enables it to be effectively used in medicinal and laboratory settings, facilitating accurate measurement and easy combination with other substances.

Comment on solubility

Solubility of [(2R,3R,4S,5R)-5-(4-acetamido-2-oxo-pyrimidin-1-yl)-3,4-diacetoxy-tetrahydrofuran-2-yl]methyl acetate

The solubility of the compound [(2R,3R,4S,5R)-5-(4-acetamido-2-oxo-pyrimidin-1-yl)-3,4-diacetoxy-tetrahydrofuran-2-yl]methyl acetate is influenced by several factors including its molecular structure and the presence of functional groups. Solubility is a critical property in many applications, particularly in pharmaceuticals, biochemistry, and chemical synthesis.

This compound contains both polar and non-polar regions:

  • Polar Functional Groups: The presence of acetamido and hydroxyl groups contributes to higher polarity, enhancing solubility in polar solvents like water.
  • Non-Polar Hydrocarbon Chains: The tetrahydrofuran ring adds hydrophobic characteristics that can decrease solubility in aqueous environments.

In general, this compound is likely to exhibit:

  • Higher Solubility in: Organic solvents such as methanol, ethanol, and dimethyl sulfoxide (DMSO).
  • Moderate Solubility in: Water due to its polar functionalities.

As a rule of thumb, “like dissolves like” can be applied, indicating that polar solvents are more effective in dissolving polar compounds like this one. For precise applications, empirical solubility tests in various solvents are recommended to fully understand its behavior.

Interesting facts

Interesting Facts about [(2R,3R,4S,5R)-5-(4-acetamido-2-oxo-pyrimidin-1-yl)-3,4-diacetoxy-tetrahydrofuran-2-yl]methyl acetate

This compound showcases the intricate interplay between organic chemistry and medicinal applications. Known for its complex structure, it is a member of the tetrahydrofuran family and has garnered interest due to its potential pharmacological properties. Here are some notable aspects:

  • Synthesis Potential: The synthesis of this compound involves multiple steps, highlighting the creativity and skill required in organic chemistry. Its preparation often utilizes advanced techniques such as protecting group strategies and coupling reactions.
  • Biological Relevance: The presence of the pyrimidine moiety is particularly fascinating, as pyrimidines are common in nucleic acids. This suggests that the compound might interact with biological systems in a meaningful way, potentially influencing DNA or RNA synthesis.
  • Medicinal Chemistry: The acetamido group attached to the pyrimidine ring could imply potential applications in therapeutic areas, especially in designing inhibitors for specific biological targets, such as enzymes involved in nucleic acid metabolism.
  • Chirality: It features multiple chiral centers, which adds an exciting layer of complexity and might affect the compound's biological activity, as chirality plays a crucial role in the interaction between drugs and their biological targets.

As showcased, this compound serves as a fascinating example of how detailed structural elements can lead to significant biological implications. It serves as a reminder of the profound connections between molecular structure and function in the realm of chemistry.

Synonyms
Tetraacetylarabinosylcytosine
6742-08-1
NSC 92717
BRN 0771368
N-Acetyl-1-beta-D-arabinofuranosylcytosine 2',3',5'-triacetate
Cytosine, N-acetyl-1-beta-D-arabinofuransyl-, 2',3',5'-triacetate
CYTOSINE, N-ACETYL-1-beta-D-ARABINOFURANOSYL-, 2',3',5'-TRIACETATE
Acetamide, N-(1,2-dihydro-2-oxo-1-(2,3,5-tri-O-acetylbeta-D-arabinofuranosyl)-4-pyrimidinyl)-
[(2R,3R,4S,5R)-5-(4-Acetamido-2-oxopyrimidin-1-yl)-4-acetyloxy-2-(acetyloxymethyl)oxolan-3-yl]acetate