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Guggulsterone

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Identification
Molecular formula
C21H28O2
CAS number
95975-55-6
IUPAC name
2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
State
State

At room temperature, Guggulsterone is in a solid state, typically crystalline in form.

Melting point (Celsius)
170.00
Melting point (Kelvin)
443.15
Boiling point (Celsius)
620.15
Boiling point (Kelvin)
893.30
General information
Molecular weight
312.45g/mol
Molar mass
312.4350g/mol
Density
1.0478g/cm3
Appearence

Guggulsterone is a natural plant sterol that appears as white to pale yellow crystalline powder. It is a steroidal compound with a complex structure often extracted from the guggul plant, Commiphora wightii.

Comment on solubility

Solubility of 2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol

The solubility of the compound 2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol (C21H28O2) can be influenced by various factors including its molecular structure, polarity, and intermolecular forces. Here are some key points to consider:

  • Polarity: This compound contains hydroxyl (-OH) groups, which can engage in hydrogen bonding, increasing its solubility in polar solvents such as water.
  • Hydrophobic Character: The significant hydrocarbon framework suggests that while it may dissolve in organic solvents, it could have limited solubility in aqueous environments.
  • Solvent Interaction: Its solubility profile can vary greatly with different solvents, meaning it might be readily soluble in solvents like ethanol or methanol, while being less soluble in hydrocarbons.

In summary, the solubility of C21H28O2 is likely to reflect a balance between its polar hydroxyl groups and the hydrophobic character of its extensive hydrocarbon structure. Thus, it is pertinent to test solubility across various solvents to obtain a nuanced understanding of this compound’s behavior in different chemical contexts.

Interesting facts

Interesting Facts About 2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol

This compound, with a rather complex name, showcases a fascinating structure that has piqued the interest of both chemists and biologists alike. As a member of the phenanthrene family, which is known for its polycyclic aromatic structure, it highlights the intricate relationship between molecular structure and biological function.

Biological Relevance

One of the most compelling aspects of this compound is its potential biological activity. Compounds with such structures are often studied for their:

  • Anticancer properties: Some phenanthrenes are observed to have effects on various types of cancer cells.
  • Anti-inflammatory effects: Research has suggested that similar compounds possess properties that may help reduce inflammation.
  • Hormonal activity: Given its diol functional groups, this compound may interact with hormone receptors, affecting biological pathways.

Synthetic Pathways

Synthesizing complex organic compounds like this one often involves multiple steps and sophisticated strategies. For example:

  • Functionalization: Various methods can be employed to introduce methoxy and methyl groups at specific positions.
  • Ring Closure: The cyclopenta[a]phenanthrene core is created through strategic cyclization reactions.
  • Site-specific Diol Formation: Creating the 3,17-diol functional group requires careful control of reaction conditions.

Key Considerations

When studying or working with this compound, consider the following key aspects:

  • Its potential as a lead compound for drug development.
  • The importance of stereochemistry and isomerism in determining its biological effects.
  • Environmental impact and stability during synthesis and storage.

In summary, 2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol not only highlights the intricacies of organic synthesis but also serves as a reminder of the profound connections between chemistry and biology. As research progresses, we may uncover even more about this intriguing compound's potential applications and effects.

Synonyms
2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
2-ME2;NSC-659853
2-Hydroxyestradiol 2-methyl-13C,d3-ether, 2-Methoxy-13C,d3-estradiol, 3,17beta-Dihydroxy-2-methoxy-13C,d3-1,3,5(10)-estratriene, 2,3,17beta-Trihydroxy-1,3,5(10)-estratriene-2-methyl-13C,d3-ether, 1,3,5(10)-Estratriene-2,3,17-triol 2-methyl-13C,d3-ether
2-Methoxy-.beta.-estradiol
NSC659853
2-Methoxy-b-estradiol
Neuro_000385
2-Methoxy-17alpha-estradiol
CHEMBL23576
SCHEMBL13123068
CHEBI:110165
HMS3268G22
AKOS015967320
ICX5608886
NS00014681
2-Methoxyestra-1(10),2,4-triene-3,17-diol
2-Methoxyestra-1,3,5(10)-triene-3,17.beta.-diol
BRD-A79248021-001-01-1
Q27189546