Skip to main content

Retinoic acid

ADVERTISEMENT
Identification
Molecular formula
C20H28O2
CAS number
302-79-4
IUPAC name
3-acetoxy-17-(1-formyl-5-methyl-3-oxo-hex-4-enyl)-16-hydroxy-4,10,13,14-tetramethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-4-carboxylic acid
State
State

At room temperature, retinoic acid is in a solid state. Due to its sensitivity to light and air, it may be found in powdered form contained within amber or opaque packaging to prevent degradation.

Melting point (Celsius)
137.00
Melting point (Kelvin)
410.15
Boiling point (Celsius)
469.50
Boiling point (Kelvin)
742.65
General information
Molecular weight
300.44g/mol
Molar mass
300.4410g/mol
Density
1.2500g/cm3
Appearence

Retinoic acid is typically a colorless to yellow solid. It can present itself in various crystalline or powder forms. When exposed to light and air, it may degrade and darken in color, so it is often stored in light-resistant containers.

Comment on solubility

Solubility of 3-acetoxy-17-(1-formyl-5-methyl-3-oxo-hex-4-enyl)-16-hydroxy-4,10,13,14-tetramethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-4-carboxylic acid (C20H28O2)

The solubility of this complex compound can be quite intriguing due to its intricate structure and functional groups. Several factors influence its solubility:

  • Polarity: The presence of functional groups like hydroxyl (–OH) and carboxylic acid (–COOH) tends to increase polarity, which can enhance solubility in polar solvents such as water.
  • Size and Structure: The overall size and hydrophobic nature of the hydrocarbon portions can lead to decreased solubility in water, promoting solubility in non-polar solvents like hexane or chloroform.
  • Hydrogen Bonding: The ability of the hydroxyl and carboxylic acid groups to engage in hydrogen bonding can significantly affect solubility. This characteristic can increase solubility in alcohols and related solvents.
  • Temperature: Solubility can vary with temperature. Generally, increasing temperature improves solubility for many organic compounds.

In summary, while 3-acetoxy-17-(1-formyl-5-methyl-3-oxo-hex-4-enyl)-16-hydroxy-4,10,13,14-tetramethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-4-carboxylic acid exhibits some degree of solubility in polar solvents due to its functional groups, the large non-polar components of its structure may hinder its overall water solubility. As such, it is likely to be more soluble in organic solvents.

Interesting facts

Interesting Facts About 3-Acetoxy-17-(1-formyl-5-methyl-3-oxo-hex-4-enyl)-16-hydroxy-4,10,13,14-tetramethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-4-carboxylic acid

This compound is a fascinating example of a complex organic molecule possessing structural features typical of steroid-like structures and natural products. Chemists and biologists alike are intrigued by its potential biological activities and applications:

  • Structural Complexity: The intricate arrangement of carbon, hydrogen, and oxygen atoms highlights the sophistication involved in organic synthesis and molecular design.
  • Biological Significance: Compounds of this nature may play crucial roles in biological systems, including hormone regulation and signaling pathways.
  • Potential Therapeutics: Researchers investigate similar compounds for their potential as therapeutic agents, particularly in the field of cancer research.
  • Natural Product Inspiration: Natural products derived from plant sources often inspire the synthesis of such complex compounds, emphasizing their significance in medicinal chemistry.

The compound features a unique combination of functional groups, including acetoxy and formyl, which can suggest pathways for further functionalization or reactivity in synthetic applications. As emphasized by renowned chemists, "The complexity of organic molecules provides endless opportunities for discovery." This compound serves as a testament to the challenges and joys of organic chemistry, offering insights into both structure and function.

In summary, as a scientist or student delving into the world of organic compounds, the study of such intricate molecules not only enhances our understanding of chemical behavior but also opens doors to new research avenues in biochemistry and pharmacology.