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Ursodeoxycholic Acid

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Identification
Molecular formula
C24H40O4
CAS number
128-13-2
IUPAC name
4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
State
State

At room temperature, ursodeoxycholic acid is typically in a solid state, appearing as a crystalline powder.

Melting point (Celsius)
203.00
Melting point (Kelvin)
476.15
Boiling point (Celsius)
183.00
Boiling point (Kelvin)
456.15
General information
Molecular weight
392.57g/mol
Molar mass
392.5730g/mol
Density
1.4500g/cm3
Appearence

Ursodeoxycholic acid appears as a white to off-white crystalline powder. It is odorless and has a bitter taste.

Comment on solubility

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

The solubility of 4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid is influenced by several factors:

  • Molecular Structure: Its complex structure, featuring multiple hydroxyl groups, can enhance interactions with polar solvents, improving solubility in those mediums.
  • Polarity: As an acid, it has both hydrophilic (water-attracting) and hydrophobic (water-repelling) characteristics, which may contribute to its solubility behavior.
  • pH Dependence: The solubility could vary with pH levels due to the ionization of the carboxylic acid functional group, thus influencing its overall solubility in aqueous solutions.

In general, the solubility of such compounds can be described with qualitative assessments, such as:

  1. Good solubility in polar solvents (like water or alcohols).
  2. Poor solubility in non-polar solvents (such as hexane).
  3. Enhanced solubility at increased temperatures due to kinetic energy promoting molecular interactions.

It is also noteworthy that the solubility characteristics are critical in applications such as pharmaceuticals, where bioavailability may be a decisive factor in the effectiveness of the compound.

Interesting facts

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

This compound is a fascinating example of a complex steroid derivative, known for its intricate structure and biological significance. Generally categorized as a trihydroxy steroid acid, it showcases the rich diversity found within the realm of organic chemistry.

Biological Relevance:

This compound plays an important role in various biochemical pathways, particularly in human physiology. Some notable aspects include:

  • Hormonal Activity: Many steroid-like compounds influence hormone functions, impacting growth, metabolism, and other physiological processes.
  • Potential Therapeutic Applications: Research suggests that compounds with similar structures may have applications in treating various ailments, including inflammatory diseases and hormonal imbalances.
  • Natural Production: Steroid derivatives are often produced naturally in organisms, making them integral to biological systems.

Chemical Structure:

The complex stereochemistry of this compound is worthy of exploration. With multiple chiral centers, its configuration greatly affects its function. The specific arrangement of its hydroxyl groups is crucial for:

  • Interactions with Receptors: The 3D shape of the molecule enables it to bind to particular receptors, influencing biological responses.
  • Metabolic Pathways: The functional groups dictate how the compound is metabolized, leading to the formation of various metabolites that may exhibit differing activities.

Analytical Techniques:

Studying this compound requires sophisticated analytical techniques. Some commonly employed methods include:

  • NMR Spectroscopy: An essential tool for elucidating the structural details and confirming the integrity of the compound.
  • Mass Spectrometry: Useful in determining the molecular weight and identifying structural features.
  • Chromatography: Employed for separation, purification, and quantification of the compound in biological samples.

In conclusion, 4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid exemplifies the intersection of complex chemistry and biological significance, providing insight into the multifaceted world of steroid derivatives.

Synonyms
SCHEMBL1755493
AKOS015965526
AC-20205
AC-34138