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Ergosterol

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Identification
Molecular formula
C28H44O
CAS number
57-87-4
IUPAC name
17-(1,5-dimethylhex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
State
State
At room temperature, ergosterol is in a solid-state. It is important in the production of Vitamin D2 when exposed to ultraviolet light.
Melting point (Celsius)
165.00
Melting point (Kelvin)
438.15
Boiling point (Celsius)
250.00
Boiling point (Kelvin)
523.15
General information
Molecular weight
396.66g/mol
Molar mass
396.6590g/mol
Density
1.0500g/cm3
Appearence

Ergosterol appears as a white to off-white crystalline powder. It is an unsaturated steroid alcohol found in ergot and yeast and is a component of fungal cell membranes, serving a similar function to cholesterol in animal cells.

Comment on solubility

Solubility of 17-(1,5-dimethylhex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol (C28H44O)

The solubility characteristics of the compound are quite intriguing due to its structural complexity and hydrophobic nature. Here are some key points regarding its solubility:

  • Solvent Compatibility: This compound is likely to be highly soluble in non-polar solvents such as hexane and chloroform, while its solubility in polar solvents like water is expected to be negligible.
  • Hydrophilic vs. Hydrophobic: The presence of a single hydroxyl (–OH) group provides a slightly polar character, yet the extensive alkyl portions dominate the molecule's behavior, making it primarily hydrophobic.
  • Temperature Influence: Solubility may increase with temperature, which is a common phenomenon for many organic compounds.
  • Applications: Understanding its solubility can be critical for potential applications in organic synthesis and material science.

In **summary**, while the hydroxyl group contributes to some solubility, the overwhelming hydrophobic characteristics suggest that this compound would not readily dissolve in water. Instead, it will favor organic solvents, reflecting its unique and complex molecular structure.

Interesting facts

Interesting Facts about 17-(1,5-dimethylhex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol

This compound is a fascinating example of a complex organic molecule that showcases the intricacies of structural chemistry and organic synthesis. It belongs to the family of **steroids**, which are characterized by their multi-ring structures and diverse biological activities.

Key Characteristics

  • Structural Complexity: The compound possesses a large framework composed of multiple fused cyclic systems, which greatly influences its reactivity and interaction with biological systems.
  • Biological Significance: Compounds like this one often exhibit steroidal properties, potentially functioning as hormones or biological precursors that regulate physiological activities.
  • Natural Occurrence: Its structural features could hint at natural origins, resembling sterols found in plant and animal membranes, which are vital for various cellular functions.

Chemical Synthesis Insights

The synthesis of such complex molecules typically involves several key techniques:

  1. Functional Group Transformations: Modifications of molecular groups to enhance reactivity or stability.
  2. Ring Formation: Strategic formation of rings, which is crucial in maintaining the integrity of the steroid structure.
  3. Chromatography: For purification, scale-up processes may utilize chromatographic techniques to isolate the desired compound from a mixture.

The detailed study of this compound not only aids in understanding its potential applications in pharmacology but also sheds light on the complex nature of organic molecules. As emphasized by many chemists, "the beauty of chemistry lies in understanding how simple elements can combine to create intricate and life-sustaining structures."

In conclusion, this compound's molecular architecture offers rich avenues for exploration in both synthetic and applied chemistry, enhancing our appreciation for the world of organic compounds.

Synonyms
Lanosta-8,24-dien-3-ol
514-47-6
NSC36571
NSC403164
Eupha-8,24-dienol
4,4,10,13,14-pentamethyl-17-(6-methylhept-5-en-2-yl)-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
MFCD00021108
4,4,10,13,14-pentamethyl-17-(6-methylhept-5-en-2-yl)-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-3-ol
911660-54-3
alpha-Eupho;Euphadienol
SCHEMBL1952146
CHEMBL4758980
DTXSID40859110
(3S,5R,10S,13S,14S,17S)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
BCP13215
LLB66054
BBL033874
NSC-36571
STL372739
AKOS025247944
NSC-403164
5.alpha.-Eupha-8,24-dien-3.beta.-ol
SY046459
VS-12323
NS00001937
13.alpha.,17.beta.H-Lanosta-8,24-dien-3.beta.-ol
Lanosta-8, (3.beta.,13.alpha.,14.beta.,17.alpha.)-
3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9H,9aH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol