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Cholesterol

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Identification
Molecular formula
C27H46O
CAS number
57-88-5
IUPAC name
(3S,5S,7R,17S)-7,10,13-trimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
State
State

Cholesterol at room temperature is typically found in a solid crystalline state. It is insoluble in water but soluble in organic solvents such as alcohol and ether.

Melting point (Celsius)
148.00
Melting point (Kelvin)
421.15
Boiling point (Celsius)
360.00
Boiling point (Kelvin)
633.15
General information
Molecular weight
386.65g/mol
Molar mass
386.6530g/mol
Density
1.0529g/cm3
Appearence

Cholesterol is a white, crystalline substance. Under a microscope, it appears as a pearly, translucent solid. Commercial samples of cholesterol are often yellowish due to impurities. This compound doesn't have a taste or odor.

Comment on solubility

Solubility of (3S,5S,7R,17S)-7,10,13-trimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol

The solubility of this complex organic compound can be influenced by several factors, given its unique structure. Here are some important considerations related to its solubility:

  • Polarity: The presence of hydroxyl (–OH) groups in the 3 and 17 positions may enhance the solubility in polar solvents, particularly water, due to the ability to form hydrogen bonds.
  • Hydrophobic Character: The extensive hydrocarbon framework contributes to hydrophobic interactions, which might limit solubility in polar solvents but enhance solubility in non-polar organic solvents such as hexane or chloroform.
  • Chain Length: The tetradecahydro group increases the overall hydrophobicity, impacting solubility, especially as the length of carbon chains often correlates with lower solubility in polar solvents.
  • Temperature Influence: Temperature can have a significant effect; often, an increase in temperature will enhance solubility in organic solvents.

In summary, while the compound may dissolve well in some organic solvents due to its hydrophobic characteristics, it may demonstrate only moderate solubility in water owing to the balance between its polar hydroxyl groups and non-polar hydrocarbon structure. As with many complex organic compounds, empirical testing will provide the most accurate assessment of solubility.

Interesting facts

Interesting Facts about (3S,5S,7R,17S)-7,10,13-trimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol

This compound, known as a complex polycyclic structure, is part of a family of steroids that exhibit fascinating biological properties. Synthesized through various natural processes, its presence in living organisms contributes significantly to physiological functions.

Biological Significance

Some intriguing aspects of this compound include:

  • Hormonal Precursor: This structure is often involved as a precursor in the biosynthesis of important hormones, showcasing its vital role in endocrinology.
  • Medicinal Applications: It is studied for potential therapeutic effects, particularly in areas such as anti-inflammatory and anticancer research.
  • Natural Sources: Often extracted from plants and animals, this compound highlights nature's remarkable ability to produce complex chemical structures that support life.

Structural Features

The unique configuration of this compound leads to various properties:

  • Stereochemistry: The specific stereochemistry, denoted by designations like (3S,5S,7R,17S), profoundly influences its reactivity and biological interactions.
  • Hydroxyl Groups: The presence of hydroxyl groups (-OH) enhances its solubility and reactivity, providing pathways for various chemical reactions.

Cultural Context

In addition to its scientific importance, this compound often garners interest in:

  • Pharmaceutical Chemistry: The synthesis and modification of such compounds are pivotal in drug discovery, making it a subject of intense study among chemists.
  • Environmental Impact: Understanding its degradation and behavior in the environment is crucial for assessing ecological risks associated with synthetic analogs.

As we continue to unravel the complexities of such compounds, it becomes increasingly clear that they not only embody the beauty of chemical diversity but also serve as a foundation for advancements in science and medicine. Exploring their intricacies opens doors to new discoveries that can enhance our understanding of life itself.