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Retinoic acid

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Identification
Molecular formula
C20H28O2
CAS number
302-79-4
IUPAC name
(1R,4aR)-1,4a,7-trimethyl-7-vinyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
State
State

At room temperature, retinoic acid is typically in a solid state as a crystalline powder. It is quite stable under standard conditions but requires protection from light.

Melting point (Celsius)
179.00
Melting point (Kelvin)
452.15
Boiling point (Celsius)
437.70
Boiling point (Kelvin)
710.85
General information
Molecular weight
300.44g/mol
Molar mass
300.4410g/mol
Density
1.2250g/cm3
Appearence

Retinoic acid typically appears as a yellow to light orange crystalline powder. The substance is sensitive to light and air, which can alter its appearance over time if not stored properly.

Comment on solubility

Solubility of (1R,4aR)-1,4a,7-trimethyl-7-vinyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid

This compound is a complex organic molecule with a unique structure, which influences its solubility properties. Solubility is a crucial physical property that determines how a substance interacts in different environments, particularly in aqueous solutions.

When considering the solubility of (1R,4aR)-1,4a,7-trimethyl-7-vinyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid, several factors come into play:

  • Polarity: The presence of the carboxylic acid group (-COOH) generally enhances the compound's ability to interact with polar solvents such as water, promoting solubility to some extent.
  • Hydrophobic Regions: The large hydrophobic hydrocarbon structure may hinder solubility in polar solvents, indicating that it may be more soluble in non-polar solvents like hexane or chloroform.
  • Temperature Effects: Temperature may also impact solubility; typically, an increase in temperature can enhance solubility for many organic compounds.
  • pH Dependencies: Since the compound contains a carboxylic acid, its solubility may vary with changes in pH, as the acid can dissociate into an anion in basic conditions, potentially increasing solubility.

Overall, the solubility of this compound will likely be moderate in polar solvents and more substantial in non-polar solvents, making the exploration of its solubility characteristics an interesting subject in solubility studies.

Interesting facts

Interesting Facts about (1R,4aR)-1,4a,7-trimethyl-7-vinyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid

(1R,4aR)-1,4a,7-trimethyl-7-vinyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid is a fascinating compound with several intriguing characteristics that warrant exploration.

Key Features:

  • Structural Diversity: This compound features a complex bicyclic structure, characteristic of many biologically active compounds. Its arrangement contributes to its potential biological activity.
  • Vinyl Group: The presence of a vinyl group imparts unique reactivity to the compound, making it a potential candidate for further chemical modifications and applications in synthetic chemistry.
  • Natural Product Derivation: Compounds similar to this one often find their origins in natural products, suggesting its relevance in medicinal chemistry and research into new pharmaceuticals.

In the realm of organic chemistry, the configuration of the compound, specifically its cis/trans and R/S stereochemistry, can greatly influence its properties and reactivity. The chirality at the 1R and 4aR positions may play a role in differentiating its biological effects and interactions with other molecules.

Potential Applications:

  • Medicinal Chemistry: Due to the structural similarity to various bioactive compounds, it holds promise in drug discovery and development.
  • Polymer Chemistry: The vinyl functionality makes it a suitable precursor for the synthesis of polymers, particularly in the production of specialty plastics.
  • Material Science: Given its intricate structure, it may serve as a model compound for studying material properties, particularly in the development of novel materials with specific qualities.

In summary, (1R,4aR)-1,4a,7-trimethyl-7-vinyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid represents a unique intersection of structure and function. Its potential applications and inherent complexities make it a noteworthy topic of study for chemists and researchers alike.

Synonyms
SCHEMBL15339339