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Cholesterol

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Identification
Molecular formula
C27H46O2
CAS number
57-88-5
IUPAC name
(8R,9S,10S,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
State
State

At room temperature, cholesterol is a solid. It is commonly found in biological tissues, making it more recognizable in that context as part of cellular membranes rather than its pure solid state.

Melting point (Celsius)
148.50
Melting point (Kelvin)
421.65
Boiling point (Celsius)
360.00
Boiling point (Kelvin)
633.15
General information
Molecular weight
386.65g/mol
Molar mass
386.6540g/mol
Density
1.0679g/cm3
Appearence

Cholesterol is a white, crystalline solid with a lustrous sheen. In its pure form, it may appear as a fine powder or in a microcrystalline form. It's odorless and tasteless. Due to its crystalline nature, it reflects light, which provides it a slightly shiny appearance.

Comment on solubility

Solubility of (8R,9S,10S,13S,14S)-10,13-dimethyl-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 organic compounds often depends on their molecular structure, including the presence of functional groups and the overall polarity of the molecule. In the case of (8R,9S,10S,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol, we can note the following aspects regarding solubility:

  • Polarity: The presence of hydroxyl (-OH) groups typically enhances solubility in polar solvents, such as water. However, the substantial hydrophobic hydrocarbon portion may inhibit solubility in such solvents.
  • Solvent Choice: This compound is likely more soluble in non-polar solvents, such as hexane or toluene, due to its large hydrocarbon backbone.
  • Temperature Dependency: Generally, solubility increases with temperature in many organic solvents, therefore, heating may improve dispersion.
  • pH Influence: The degree of ionization of hydroxyl groups can also depend on the pH, which may further affect solubility in aqueous solutions.

Therefore, while (8R,9S,10S,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol exhibits potential challenges due to its hydrophobic characteristics, it may still find adequate solubility within specific non-polar or organic solvent environments.

Interesting facts

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

This intriguing compound is a member of the steroid class and has garnered attention primarily for its unique structure and potential biological activities. Here are some captivating facts:

  • Steroidal Structure: The complex structure features multiple fused rings which are characteristic of steroids, influencing both its chemical behavior and biological activity.
  • Biological Significance: Compounds like this one are of interest in drug development due to their ability to interact with hormonal pathways in the body, potentially leading to medicinal applications.
  • Stereochemistry: The specific stereochemistry denoted by its nomenclature highlights the importance of chirality in biological systems. Chiral molecules can exhibit significantly different biological activities based on their orientation.
  • Research Potential: Ongoing studies focus on the role such compounds may play in therapies for conditions like hormone replacement therapy and certain cancers, underscoring the relevance of steroid derivatives in medicine.
  • Historical Context: The exploration of compounds with similar frameworks has a long history in organic chemistry, contributing to the robust understanding of natural products.
  • Green Chemistry: The development of synthetic pathways to create such complex molecules often employs sustainable practices, which are increasingly important in modern chemistry.

In conclusion, (8R,9S,10S,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol stands as a remarkable example of how intricate molecular structures can lead to significant insights in chemistry and potential therapeutic applications. Researchers continue to unlock the mysteries of such compounds, emphasizing the need for rigorous investigation into their properties and effects.

Synonyms
ANDROSTANE-3,17-DIOL
CHEBI:27727
DTXSID00859494
5 alpha Androstane 3 alpha,17 beta diol
5 Androstane 3,17 diol
5-Androstane-3,17-diol
5 alpha-Androstane-3alpha,17 beta-diol
Androstane 3,17 diol
RefChem:915831
DTXCID001333656
5 alpha Androstane 3alpha,17 beta diol
5 alpha Androstane 3 beta,17 beta diol
5 beta Androstane 3 alpha,17 beta diol
Androstanediol
25126-76-5
ANDROSTANDIOL
(3aS,3bR,9aS,9bS,11aS)-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthrene-1,7-diol
(8R,9S,10S,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
SCHEMBL3366554
5.xi.-Androstane-3,17-diol
5beta-Androstan-3alpha,17alpha-diol
5.xi.-Androstane-3.xi.,17.xi.-diol
DB-310117
Q27103288