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Retinoic acid

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Identification
Molecular formula
C20H28O2
CAS number
302-79-4
IUPAC name
5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-en-1-yl]-3-methyl-penta-2,4-dienoic acid
State
State

At room temperature, retinoic acid is in a solid state. It retains its crystalline form providing the typical solid nature expected from an organic acid compound in this group.

Melting point (Celsius)
179.50
Melting point (Kelvin)
452.70
Boiling point (Celsius)
494.60
Boiling point (Kelvin)
767.80
General information
Molecular weight
300.45g/mol
Molar mass
300.4390g/mol
Density
1.1156g/cm3
Appearence

Retinoic acid is typically a yellow to light orange crystalline solid. It is known for its bright, lively appearance, which is characteristic of many carotenoids. The crystalline nature of retinoic acid contributes to its stability and its distinct textures when viewed closely.

Comment on solubility

Solubility of 5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-en-1-yl]-3-methyl-penta-2,4-dienoic acid

The solubility of 5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-en-1-yl]-3-methyl-penta-2,4-dienoic acid in various solvents can exhibit intriguing characteristics. As a compound with both acidic functional groups and multiple hydrophobic segments, its solubility profile can be influenced by the following factors:

  • Polarity: The presence of the carboxylic acid group typically enhances solubility in polar solvents such as water.
  • Hydrophobic regions: The significant hydrophobic character due to the cyclohexene rings and alkyl chains can hinder solubility in water, whereas it may show better solubility in organic solvents like ethanol or acetone.
  • Temperature: As with many organic acids, an increase in temperature might improve solubility in solvents where it is partially soluble.
  • pH Dependency: The acid's solubility may vary depending on the pH of the solution, as deprotonation at higher pH levels can enhance its anionic solubility in aqueous conditions.

In summary, the solubility of this compound is a complex interplay of its molecular structure and environmental conditions. Generally, water solubility might be limited due to hydrophobic elements, yet it can dissolve more readily in non-polar solvents or under conditions that favor its ionic form. Exploring these different aspects of solubility can provide a deeper understanding of the compound's behavior in various chemical contexts.

Interesting facts

Interesting Facts about 5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-en-1-yl]-3-methyl-penta-2,4-dienoic acid

This intriguing compound, known for its complex structure, plays a notable role in various biological systems. Here are some fascinating aspects that shed light on its significance:

  • Natural Occurrence: This compound is often found in nature, particularly in certain plants and fungi, where it contributes to their metabolic processes.
  • Biological Activity: It exhibits properties that may influence cellular functions, possibly acting as a biochemical regulator.
  • Structural Characteristics: The unique cyclohexenone structure contributes to its reactivity and biological interactions, particularly in enzyme catalysis.
  • Potential Applications: Due to its biochemical properties, researchers are investigating its potential in pharmacology and agriculture; it may lead to the development of new therapeutic agents or pest management solutions.
  • Synthesis Challenges: The multi-step synthesis of this compound can be quite challenging in the lab, often requiring advanced techniques and careful control of reaction conditions.

As a notable member of the family of organic compounds, understanding 5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-en-1-yl]-3-methyl-penta-2,4-dienoic acid not only enhances our knowledge of chemical interactions but also opens doors to advancements in science and technology.

Synonyms
(+)-Abscisic acid
SCHEMBL3107122
AKOS030241778
AB02708
(s)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentanedienoic acid