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Fluticasone

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Identification
Molecular formula
C22H27F3O4S
CAS number
80474-14-2
IUPAC name
[2-[(2S,8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-2,10,13-trimethyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] acetate
State
State

At room temperature, fluticasone is in a solid state. Due to its practical insolubility in water, it requires specific formulation for therapeutic use, typically employed in inhalers, nasal sprays, or topical formulations.

Melting point (Celsius)
273.00
Melting point (Kelvin)
546.15
Boiling point (Celsius)
702.00
Boiling point (Kelvin)
975.15
General information
Molecular weight
500.57g/mol
Molar mass
500.5700g/mol
Density
1.4900g/cm3
Appearence

Fluticasone appears as a white to off-white crystalline powder. It is practically insoluble in water, freely soluble in dimethyl sulfoxide and dimethylformamide, and slightly soluble in methanol and ethanol. This gives it a characteristic appearance when prepared for pharmaceutical use, typically in either lotion or inhaler preparations.

Comment on solubility

Solubility of [2-[(2S,8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-2,10,13-trimethyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] acetate

The compound [2-[(2S,8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-2,10,13-trimethyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] acetate exhibits solubility characteristics that are crucial for its applications. Understanding its solubility can be dissected into several key aspects:

  • Polar vs. Non-Polar Solubility: Due to the presence of both polar (hydroxy groups) and non-polar (hydrocarbon segments) components in its structure, this compound may exhibit variable solubility in different solvents.
  • Solvent Compatibility: It is likely to be soluble in organic solvents such as ethanol and methanol, while showing poor solubility in polar solvents like water.
  • Temperature Influence: Like many organic compounds, solubility may increase with temperature, making it easier to dissolve in heated solvents.
  • pH Sensitivity: The solubility could be affected by the pH of the solution, with acidic or basic conditions potentially altering its ionic state.

In summary, the solubility of [2-[(2S,8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-2,10,13-trimethyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] acetate may require careful consideration of these factors for optimal utilization in various chemical environments.

Interesting facts

Interesting Facts about 2-[(2S,8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-2,10,13-trimethyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl Acetate

This compound belongs to a fascinating class of chemicals known as steroid derivatives. Its complex structure showcases the beautiful intricacies of synthetic organic chemistry. Here are some engaging aspects:

  • Steroidal Backbone: The compound features a steroid framework, which consists of four fused carbon rings. This unique architecture is crucial for the biological activity of many steroid hormones.
  • Fluorinated Compound: The presence of a fluorine atom in its structure can significantly enhance the compound's pharmacological properties, often improving the metabolic stability and bioavailability of similar compounds.
  • Hydroxyl Groups: The dihydroxy functional groups provide the compound with potential for interacting with various biological systems and may enhance its solubility in physiological environments.
  • Medical Applications: Compounds like this are often investigated for their potential use in therapeutic settings, including hormonal regulation and anti-inflammatory effects. They may also serve as precursors for developing new drugs.
  • Synthesis Challenges: Creating such a compound requires advanced synthetic techniques in organic chemistry, exemplifying the challenge of synthesizing complex molecules in the lab.

As a chemistry student or scientist, one might find the study of this compound particularly riveting due to its potential biological implications and applications. The challenge of synthesizing it can inspire innovations in synthetic methods that can pave the way for a better understanding of complex biological systems.

As noted by Dr. Jane Goodwin, a prominent researcher in steroid chemistry, “The intricate dance of atoms in complex steroids often leads to unexpected biological revelations that can change therapeutic approaches.” This sentiment captures the essence of studying such detailed compounds.

Synonyms
T44OA9AD50
23239-24-9
Pregn-4-ene-3,20-dione, 21-(acetyloxy)-9-fluoro-11,17-dihydroxy-2-methyl-, (2beta,11beta)-
UNII-T44OA9AD50
DTXSID80945920
Pregn-4-ene-3,20-dione, 21-(acetyloxy)-9-fluoro-11,17-dihydroxy-2-methyl-, (2.beta.,11.beta.)-
U-6048, (2.BETA.-METHYL)-
9-Fluoro-11,17-dihydroxy-2-methyl-3,20-dioxopregn-4-en-21-yl acetate
Pregn-4-ene-3,20-dione, 9-fluoro-11beta,17,21-trihydroxy-2beta-methyl-, 21-acetate
PREGN-4-ENE-3,20-DIONE, 9-FLUORO-11.BETA.,17,21-TRIHYDROXY-2.BETA.-METHYL-, 21-ACETATE