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Retinol

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Identification
Molecular formula
C20H30O
CAS number
68-26-8
IUPAC name
(1S)-3-[2-[(1R,3aS,7aR)-1-[(1R,4S)-5-hydroxy-1,4,5-trimethyl-hex-2-enyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol
State
State

At room temperature, retinol is typically found as a solid or a viscous liquid, depending on its specific form and how it's manufactured or stored.

Melting point (Celsius)
64.00
Melting point (Kelvin)
337.15
Boiling point (Celsius)
137.00
Boiling point (Kelvin)
410.15
General information
Molecular weight
286.46g/mol
Molar mass
286.4570g/mol
Density
0.9440g/cm3
Appearence

Retinol is a yellow to pale yellow crystalline compound. It can also appear as a viscous, oily liquid depending on its storage conditions and its purity. In solid form, it can sometimes break down easily, which is why it is often found in a more stable derivative form, such as in vitamin supplements.

Comment on solubility

Solubility of (1S)-3-[2-[(1R,3aS,7aR)-1-[(1R,4S)-5-hydroxy-1,4,5-trimethyl-hex-2-enyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol

The solubility of (1S)-3-[2-[(1R,3aS,7aR)-1-[(1R,4S)-5-hydroxy-1,4,5-trimethyl-hex-2-enyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol can be understood through several key factors that affect how well this compound interacts with solvents.

Factors Influencing Solubility:

  • Polarity: Polarity plays a crucial role in solubility. The presence of hydroxyl (?OH) groups can promote interaction with polar solvents such as water.
  • Hydrophobic Regions: The large hydrophobic sections of the molecule may hinder solubility in polar solvents, while enhancing solubility in nonpolar solvents.
  • Temperature: Generally, solubility increases with temperature; however, it can vary significantly based on the compound's structure.
  • Hydrogen Bonding: The ability of this compound to form hydrogen bonds with solvents may enhance its solubility in compatible media.

In summary, the solubility of (1S)-3-[2-[(1R,3aS,7aR)-1-[(1R,4S)-5-hydroxy-1,4,5-trimethyl-hex-2-enyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol can be described as varies based on the environmental conditions and the solvent used. The interaction between polar and nonpolar characteristics of the molecule can lead to unique solubility behavior, making it a subject of interest for further study.

Interesting facts

Interesting Facts about (1S)-3-[2-[(1R,3aS,7aR)-1-[(1R,4S)-5-hydroxy-1,4,5-trimethyl-hex-2-enyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol

This compound is a fascinating example of a complex organic molecule with significant potential in the realm of chemistry and natural product synthesis. Here are some interesting insights into its structure and applications:

  • Terpenoid Significance: The compound stems from the vast and diverse group of terpenoids, which are well-known for their roles in natural substances, such as essential oils and fragrances. Terpenoids often exhibit unique biological activity, making them invaluable in pharmaceuticals and perfumery.
  • Stereochemistry: The specific stereochemical configuration of this compound allows it to engage in selective interactions with biological macromolecules. The chirality, represented by the (1S) and (1R) descriptors, is critical in determining the compound's reactivity and pharmacological properties.
  • Potential Health Benefits: Research indicates that many terpenoids possess anti-inflammatory, antimicrobial, and anticancer properties. While the exact effects of this compound require further investigation, its structural complexity suggests potential as a lead compound in drug discovery.
  • Natural Sources: Many similar compounds are biosynthesized in plants, often serving to protect against herbivores or infections. This compound may offer insights into the ecological functions of plant metabolites.
  • Synthesis and Challenges: The synthesis of such complex molecules is a challenge in organic chemistry, often requiring innovative strategies like total synthesis or biocatalysis. Understanding the steps involved can enhance skills in laboratory techniques and mechanisms.

In summary, the multifaceted nature of (1S)-3-[2-[(1R,3aS,7aR)-1-[(1R,4S)-5-hydroxy-1,4,5-trimethyl-hex-2-enyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol extends beyond its molecular and functional attributes. It stands as a captivating subject for ongoing research and exploration in the fields of chemistry and medicinal science.

Synonyms
NS00122863