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Cholesterol

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Identification
Molecular formula
C27H46O
CAS number
57-88-5
IUPAC name
(5S,8R,9S,10S,13S,14S,17S)-2-(hydroxymethyl)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
State
State

At room temperature, cholesterol is a solid that is waxy in nature. It is insoluble in water but soluble in alcohols and other organic solvents, allowing it to be incorporated into household products and pharmaceuticals.

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
386.6530g/mol
Density
1.0520g/cm3
Appearence

Cholesterol appears as a white, crystalline solid. It can form pearly, leaf-like crystals when derived from drying alcohol solutions. It is often encountered as a component of dietary products, where it is in a complex mixture with other lipids.

Comment on solubility

Solubility of (5S,8R,9S,10S,13S,14S,17S)-2-(hydroxymethyl)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

This complex organic compound features multiple chiral centers and hydrophobic regions, which significantly influence its solubility characteristics. Here are some key points regarding its solubility:

  • Hydroxymethyl Group Influence: The presence of the -OH group contributes to its potential solubility in polar solvents like water, albeit to a limited extent due to the large hydrophobic moieties.
  • Hydrophobic Characteristics: With multiple methyl groups and a dodecahydro structure, the compound exhibits significant hydrophobic character, which generally favors solubility in non-polar solvents, such as hexane or chloroform.
  • Solvent Specificity: Solubility is often solvent-dependent; in mixtures of polar and non-polar solvents, such as ethanol or methanol combined with pentane, the compound may show variable solubility behaviors.

Overall, while this compound can achieve some level of solubility in polar solvents due to the hydroxymethyl group, its complex hydrophobic structure primarily directs it towards non-polar environments. Therefore, the solubility of this molecule can be described as limited in aqueous solutions, yet favorable in organic solvents.

Interesting facts

Interesting Facts about (5S,8R,9S,10S,13S,14S,17S)-2-(hydroxymethyl)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

This complex compound is a fascinating example of a steroid, showcasing the intricate nature of organic chemistry. Derived from natural sources, it contributes significantly to various biological processes and has potential pharmacological applications.

Key Characteristics

  • Stereochemistry: The compound exhibits a specific arrangement of atoms, which contributes to its unique biological activities. The specificity of stereocenters can be crucial in distinguishing between biologically active and inactive forms.
  • Hydroxymethyl Group: The presence of the hydroxymethyl group enhances its reactivity and potential interactions with biological molecules, making it a point of interest in medicinal chemistry.
  • Dimethyl Substituents: The dimethyl groups are significant as they can affect the compound's conformation and, consequently, its biological interactions.

Biological Significance

The structural framework of this compound allows for interaction with various enzymes and receptors in the human body. Specifically, compounds similar to this one have been studied for their roles in:

  • Hormonal activity, aligning with the role of steroids in human physiology.
  • Potential applications in cancer therapy, as some steroidal compounds can modulate cell proliferation.
  • Anti-inflammatory properties which contribute to the therapeutic landscape for chronic conditions.

As a compound rich in potential, ongoing research continues to explore its capabilities, underscoring the importance of understanding chemical structures in the realm of biological and medicinal chemistry.

Synonyms
566-53-0
17-beta-Hydroxy-5-alpha-androst-2-ene-2-methanol
NSC 63015
BRN 1987515
2-Hydroxymethyl-5-alpha-androst-2-en-17-beta-ol
NSC63015
5-alpha-ANDROST-2-ENE-2-METHANOL, 17-beta-HYDROXY-
DTXSID80972039
NSC-63015
2-(hydroxymethyl)androst-2-en-17-ol