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Tauroursodeoxycholic acid

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Identification
Molecular formula
C26H45NO6S
CAS number
14605-22-2
IUPAC name
2-[4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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 a solid at room temperature. It is stable under normal conditions, meaning it maintains its state without transitioning to a liquid or gas unless subjected to high temperatures beyond normal ambient conditions. It is usually stored in a cool, dry place to maintain its efficacy and prevent degradation.
Melting point (Celsius)
146.00
Melting point (Kelvin)
419.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
499.71g/mol
Molar mass
499.7070g/mol
Density
1.2200g/cm3
Appearence

Tauroursodeoxycholic acid (TUDCA) is a white to off-white crystalline powder, appearing uniform and fine to the touch. Its crystalline nature gives it a sparkling appearance under light, typical of many such organic compounds. When commercialized, it is often presented in capsules or as a pure dry powder, noting the importance of its integrity and shelf-stability.

Comment on solubility

Solubility of 2-[4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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 the compound, 2-[4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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 key factors:

  • Polarity: Given its sulfonic acid group, this compound displays a higher degree of polarity, which generally enhances solubility in water and polar solvents.
  • Acidic Properties: The presence of the sulfonic acid group contributes to its solubility in aqueous solutions due to its ability to ionize and form soluble ions.
  • Hydrogen Bonding: The hydroxyl (-OH) groups present in the structure can engage in hydrogen bonding, further increasing its solubility in polar solvents.

However, due to the complex overall structure, solubility might be limited in certain non-polar solvents. Therefore, it is crucial to consider the **medium** in which this compound is dissolved:

  • Aqueous solutions: Likely to demonstrate good solubility.
  • Non-polar solvents: Poor solubility anticipated due to the hydrophilic nature of the functional groups.

In summary, 2-[4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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 likely to be soluble in polar solvents, particularly water, due to its ionic, polar, and hydrogen bonding characteristics.

Interesting facts

Interesting Facts about 2-[4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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 complex compound is a fascinating example of the intricate world of organic chemistry, specifically in the realm of steroidal and sulfonic acid derivatives. Its unique structure includes multiple chiral centers that dictate its three-dimensional orientation, which is essential for the functionality of biologically active molecules.

Key Features:

  • Biological Relevance: Compounds with similar structures often play crucial roles in biological systems, such as signaling pathways and steroid hormone functions.
  • Chirality: The numerous chiral centers (indicated by R and S configurations) highlight the importance of stereochemistry in determining the compound's interactions with biological macromolecules.
  • Sulfonic Acids: The ethanesulfonic acid component indicates that this compound may have properties beneficial for solubility and ionization in various biological environments.
  • Research Applications: This compound could have potential applications in pharmaceutical research, particularly in the development of new therapies that target hormonal pathways or cell signaling processes.

To quote renowned chemist Robert H. Grubbs, “Science is a process that redefines itself, and in doing so, gives rise to an ever-increasing understanding of the molecules that govern life.” The study of such complex compounds broadens our understanding of biological interactions and paves the way for future discoveries.

In summary, the intricacy and potential applications of 2-[4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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 make it an intriguing subject of study for chemists and biologists alike. The ongoing exploration of its properties and functionalities continues to inspire innovative research in medicinal chemistry.

Synonyms
SCHEMBL20204256