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Fluocinolone acetonide

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Identification
Molecular formula
C24H30F1O6
CAS number
67-73-2
IUPAC name
19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
State
State

Fluocinolone acetonide is in a solid state at room temperature, typically appearing as a crystalline powder. Its stability and efficacy in topical formulations make it a common choice in dermatological treatments.

Melting point (Celsius)
272.00
Melting point (Kelvin)
545.15
Boiling point (Celsius)
298.80
Boiling point (Kelvin)
571.95
General information
Molecular weight
452.49g/mol
Molar mass
452.4900g/mol
Density
1.4490g/cm3
Appearence

Fluocinolone acetonide appears as a white to off-white crystalline powder. It is practically odorless and is insoluble in water, but soluble in alcohol and acetone. The compound is used in topical applications for its anti-inflammatory properties.

Comment on solubility

Solubility of 19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one (C24H30F1O6)

The solubility of the compound 19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one in various solvents is influenced by its complex structure and specific functional groups. Here are some key points to consider:

  • Hydrophilicity vs. Hydrophobicity: The presence of multiple hydroxy groups (-OH) suggests a degree of hydrophilicity, making it potentially soluble in polar solvents like water. However, the hydrophobic methyl groups may counteract this.
  • Solvent Interaction: Solubility may be enhanced in organic solvents such as ethanol or acetone due to lower polarity compared to water.
  • Temperature Dependency: Like many organic compounds, solubility can be temperature-dependent; hence, higher temperatures might improve solubility in some solvents, while lower temperatures may reduce it.
  • Crystallography: The compound's solid-state structure may reveal insights into solubility; poorly soluble compounds often exhibit high crystallinity, affecting dissolution rates.

Overall, predicting the solubility of this intricate compound necessitates careful consideration of its molecular interactions and physical properties. Understanding these aspects can guide effective use in various applications and formulations.

Interesting facts

Interesting Facts About 19-Fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

This compound, though complex, is a fascinating example of contemporary chemical synthesis and modification due to its unique properties and structural characteristics. Here are some engaging facts to consider:

  • Fluorine Inclusion: The presence of a fluorine atom not only influences the compound's reactivity but also enhances its biological activity, which is critical in pharmaceutical applications.
  • Multi-cyclic Structure: The pentacyclic structure is a rare feature in organic chemistry, leading to intriguing conformational possibilities that can impact how it interacts with biological systems.
  • Potential Therapeutic Uses: Due to its hydroxyl and acetyl groups, this compound may demonstrate promising activity in medicinal chemistry, particularly in anti-inflammatory or analgesic contexts, echoing the properties of certain steroid-like compounds.
  • Synthetic Complexity: The synthesis of such compounds often requires advanced techniques in organic synthesis, making it a valuable topic for students interested in synthetic methodologies.
  • Research Significance: Compounds derived from similar classes are often subjects of research in fields such as drug development and materials science, highlighting the interdisciplinary nature of modern chemistry.

Furthermore, the intricate design of such compounds allows chemists to fine-tune their properties for desired outcomes in practical applications. As noted by researchers in the field, "Exploring the potential of complex organic molecules can lead to groundbreaking advancements in therapeutic agents and materials." This illustrates the ongoing exploration in organic chemistry aimed at harnessing the unique attributes of complex compounds like 19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one.

Synonyms
Nasalide
SCHEMBL13026142
DTXSID70859805
XSFJVAJPIHIPKU-UHFFFAOYSA-N
BCP27631
Pregna-1,4-diene-3,20-dione, 6-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (6.alpha.,11.beta.,16.alpha.)-
Nisolid;Nasalide;RS-3999;RS 3999;RS3999
(6.alpha.,11.beta.,16.alpha.)-6-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione
12-Fluoro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H,8H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
12-Fluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one #
19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
6.alpha.-Fluoro-11.beta.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17acetal with acetone
6.alpha.-Fluoro-11.beta.,21-dihydroxy-16.alpha.,17.alpha.-(isopropylidenedioxy)pregna-1,4-diene-3,20-dione
Pregna-1,4-diene-3,20-dione, 6-.alpha.-fluoro-11-.beta.,16-.alpha.,17,21-tetrahydroxy-,cyclic 16,17-acetal with acetone