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Retinoic acid

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Identification
Molecular formula
C20H28O2
CAS number
302-79-4
IUPAC name
2-[(3R,4S,5S,8S,10S,11R,13R,14S,16S)-16-acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methyl-hept-5-enoic acid
State
State

Retinoic acid is typically found in a solid state at room temperature.

Melting point (Celsius)
184.50
Melting point (Kelvin)
457.65
Boiling point (Celsius)
617.30
Boiling point (Kelvin)
890.45
General information
Molecular weight
300.45g/mol
Molar mass
300.4410g/mol
Density
1.0483g/cm3
Appearence

Retinoic acid is a yellow to light orange crystalline solid.

Comment on solubility

Solubility of 2-[(3R,4S,5S,8S,10S,11R,13R,14S,16S)-16-acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methyl-hept-5-enoic acid

The solubility of a compound can significantly influence its application and effectiveness, and the compound in question presents a notable case. It comprises a complex structure, which suggests varied solubility behaviors. A few key points regarding its solubility characteristics include:

  • Hydrophobic vs. Hydrophilic: Due to its large hydrocarbon framework and the presence of several hydrophobic groups, this compound is likely more soluble in organic solvents rather than in aqueous solutions.
  • Potential for Ester Formation: The acetoxy group might allow for some degree of compatibility with polar solvents through hydrogen bonding, but overall, it would still favor non-polar environments.
  • Temperature Dependence: Solubility can also be affected by temperature; increasing temperature may enhance solubility in some organic solvents.

As a general observation, compounds like this often demonstrate limited solubility in water, which is common for larger organic molecules. Therefore, it is often best utilized in non-polar or mildly polar solvents for optimal effectiveness.

In conclusion, understanding the solubility characteristics of such a complex chemical structure is crucial for its practical applications and interventions in scientific and industrial settings.

Interesting facts

Interesting Facts about 2-[(3R,4S,5S,8S,10S,11R,13R,14S,16S)-16-acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methyl-hept-5-enoic acid

This remarkable compound belongs to a class of chemicals with complex structures, often found in nature and associated with various biological activities. Here are some intriguing facts and insights about this intriguing molecule:

  • Bioactive Potential: Organic compounds with structural similarities to this one have shown significant bioactivity, which can include anti-inflammatory, antioxidant, and potential anticancer properties.
  • Stereochemistry: The designation of stereochemistry (R and S configurations) indicates the compound's chirality, making it a fascinating subject for studies related to drug design where stereoisomerism can impact efficacy and safety.
  • Natural Occurrence: Compounds that feature similar carbon skeletons can often be derived from natural sources, such as plant materials. Investigating their sources may lead to new insights into natural product chemistry.
  • Applications: Due to its complex structure, this compound might be explored for usage in fields like pharmacology, biochemistry, and materials science, demonstrating the interdisciplinary nature of modern scientific research.
  • Structural Diversity: The multitude of functional groups present in this molecule creates opportunities for synthetic chemists to explore diverse reactivity patterns, potentially leading to the development of novel compounds.

In conclusion, 2-[(3R,4S,5S,8S,10S,11R,13R,14S,16S)-16-acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methyl-hept-5-enoic acid encapsulates both complexity and potential, serving as a reminder of the richness of organic chemistry and its relevance to human health and the environment. Engaging with such compounds can inspire the next generation of chemists to delve deeper into the wonders of molecular science.

Synonyms
Spectrum_000821
Spectrum2_001267
Spectrum3_000438
Spectrum4_000638
KBioGR_001256
KBioSS_001301
DivK1c_000077
SPBio_001234
KBio1_000077
KBio2_001301
KBio2_003869
KBio2_006437
KBio3_001276
NINDS_000077