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Retinoic acid (acid form of Vitamin A)

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Identification
Molecular formula
C20H28O3
CAS number
302-79-4
IUPAC name
2-(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

At room temperature, retinoic acid is typically a solid. It does not readily evaporate and maintains a stable state unless subjected to heat or chemical reaction conditions.

Melting point (Celsius)
172.00
Melting point (Kelvin)
445.15
Boiling point (Celsius)
546.80
Boiling point (Kelvin)
819.95
General information
Molecular weight
300.44g/mol
Molar mass
300.4410g/mol
Density
1.2260g/cm3
Appearence

Retinoic acid typically appears as a pale yellow powder or crystalline solid. Its coloration can be light due to its structure and level of purity.

Comment on solubility

Solubility of 2-(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 profile of the compound C20H28O3 can be complex due to its intricate structure, which includes multiple hydroxyl groups and an alkene functional group. Here are some important points to consider:

  • Polar Groups: The presence of hydroxyl (–OH) groups generally enhances the solubility of organic compounds in polar solvents, such as water.
  • Hydrophobic Character: The alkyl chains and the cyclic structure contribute to a hydrophobic character, potentially limiting solubility in polar solvents.
  • Solvent Compatibility: This compound is likely to be more soluble in non-polar to moderately polar organic solvents like:
    • Chloroform
    • Dichloromethane
    • Ethyl acetate

In conclusion, while the polar –OH groups might suggest good solubility in water, the overall structure of the compound indicates that it may be better suited to dissolution in organic solvents. As a result, it is crucial to consider both the polar and non-polar features of the compound when predicting solubility.

Interesting facts

Interesting Facts about 2-(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 compound, known for its intricate structure and biochemical significance, falls within a fascinating realm of organic chemistry. Here are some engaging facts:

  • Complex Structure: The compound features a highly branched carbon framework, which is a hallmark of bioactive molecules. The presence of multiple functional groups like acetoxy and hydroxy indicates its potential reactivity in chemical reactions and biological pathways.
  • Natural Product Potential: Compounds with similar structural motifs are often found in natural products, particularly in the realm of steroids and terpenoids. This suggests that it might possess interesting pharmacological properties, warranting further investigation.
  • Chirality: The numerous chiral centers in this compound contribute to its stereochemical complexity, which can lead to different biological activities depending on the orientation of these centers.
  • Biological Relevance: Analogous compounds have been studied for their potential therapeutic effects, including anti-inflammatory, anti-cancer, and hormonal activities. Further exploration could reveal its roles in medicinal chemistry.
  • Applications in Synthesis: Due to its unique chemical architecture, it could serve as a valuable synthetic intermediate for the development of other complex organic molecules.

In conclusion, 2-(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 is not just a fascinating structural entity but also a potential key player in various fields of research including pharmacology, synthesis, and biochemistry. Its study may pave the way for novel discoveries in the domain of organic compounds.

Synonyms
DTXSID00859535
SY056012
DB-055357
(17E)-16-(Acetyloxy)-3,11-dihydroxy-4,8,14-trimethyl-18-norcholesta-17,24-dien-21-oic acid
2-[2-(acetyloxy)-7,10-dihydroxy-3a,3b,6,9a-tetramethyl-dodecahydro-2H-cyclopenta[a]phenanthren-1-ylidene]-6-methylhept-5-enoic acid