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Tauroursodeoxycholic acid (TUDCA)

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Identification
Molecular formula
C26H45NO6S
CAS number
14605-22-2
IUPAC name
2-[4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acid
State
State
Tauroursodeoxycholic acid is typically a solid at room temperature. It is often supplied as a crystalline powder and should be stored in a cool, dry area to maintain its stability and efficacy. The compound is sensitive to moisture and should be handled with care to prevent degradation.
Melting point (Celsius)
203.00
Melting point (Kelvin)
476.15
Boiling point (Celsius)
489.15
Boiling point (Kelvin)
762.30
General information
Molecular weight
499.71g/mol
Molar mass
499.7010g/mol
Density
1.4780g/cm3
Appearence

Tauroursodeoxycholic acid typically appears as a white crystalline powder. It is often noted for its crystalline structure and fine granularity. Due to its hydrophilic nature, it is easily dissolved in water, and the powder is often used in biochemical research and pharmaceutical formulations.

Comment on solubility

Solubility of 2-[4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acid

The solubility of 2-[4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acid is influenced by several factors that are crucial to understanding its behavior in different environments:

  • Polarity: As a sulfonic acid, this compound exhibits strong polarity. This characteristic generally enhances solubility in polar solvents such as water.
  • Hydrogen Bonding: The presence of hydroxyl groups allows for effective hydrogen bonding with water, further contributing to its solubility.
  • Chain Length: The long hydrocarbon structure may impact solubility, as increased chain length can lead to lower solubility in polar solvents.
  • Acidity: Being an acid, its ability to dissociate in solution can also affect solubility, as the conjugate base may be more soluble than the neutral form.

In summary, this compound's solubility is likely to be high in aqueous environments due to its polar nature and the ability to form hydrogen bonds. However, its complex structure may lead to variability in solubility depending on the specific conditions of the solvent and solute interactions.

Interesting facts

Interesting Facts about 2-[4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acid

This compound, often linked to biological systems and various applications, belongs to a class of chemicals that demonstrate fascinating interactions within human physiology. Here are some interesting aspects of this complex molecule:

  • Structural Diversity: The intricate structure of this compound, featuring multiple chiral centers, exemplifies the rich diversity found in nature's library of organic compounds.
  • Biological Significance: Compounds like this one can play critical roles in cellular processes. They may act as signaling molecules or functional groups within larger biochemical networks.
  • Potential Therapeutic Applications: Due to its unique structure, this molecule could be investigated for potential therapeutic uses in hormonal regulation or targeting specific pathways in disease.
  • Synthetic Challenges: The synthesis of such a complex compound presents a wide range of challenges. The need to create multiple stereocenters often requires innovative strategies in organic synthesis.
  • Research Potential: With ongoing studies in the field of medicinal chemistry, compounds like this are crucial for understanding how slight alterations in structure can affect biological activity and efficacy.

As chemistry professionals, it's essential to recognize and appreciate the craftsmanship in synthesizing and characterizing such complex molecules. The study of this particular compound not only broadens our understanding of organic chemistry but also enhances our knowledge about potential applications in healthcare and biotechnology. Emphasizing the interplay between structure and function remains a pivotal aspect of research in this field.

Synonyms
Lithocholic acid taurine conjugate
Lithocholyltaurine
2-[4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acid
SCHEMBL18762171