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Fluticasone propionate

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Identification
Molecular formula
C25H31F1O5S1
CAS number
80474-14-2
IUPAC name
[2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxo-ethyl] dihydrogen phosphate
State
State

At room temperature, Fluticasone propionate is in a solid state, appearing as a crystalline powder, which is commonly used in respiratory medications.

Melting point (Celsius)
273.20
Melting point (Kelvin)
546.30
Boiling point (Celsius)
599.90
Boiling point (Kelvin)
872.90
General information
Molecular weight
500.56g/mol
Molar mass
500.5590g/mol
Density
1.4900g/cm3
Appearence

Fluticasone propionate appears as a white powder. It is often used in its micronized form for inhalation therapies and is generally non-volatile.

Comment on solubility

Solubility of 2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxo-ethyl dihydrogen phosphate

The solubility of the compound 2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxo-ethyl dihydrogen phosphate can be characterized by several key factors:

  • Polarity: The presence of the dihydrogen phosphate group typically indicates a degree of **hydrophilicity**, suggesting that the compound may be soluble in polar solvents like water.
  • Hydrogen Bonding: This compound is capable of forming hydrogen bonds due to its hydroxyl (-OH) and phosphate groups, which could enhance its solubility in aqueous solutions.
  • Structural Complexity: The overall complexity of the molecular structure, including multiple chiral centers and functional groups, may influence solubility in organic solvents.
  • Temperature Dependency: Like many compounds, solubility may be **temperature dependent**, with increased temperatures potentially leading to higher solubility.

In conclusion, while the specific solubility of this compound requires experimental validation, its structure suggests a propensity for solubility in both polar and possibly some non-polar solvents, making it a versatile compound for various applications.

Interesting facts

Interesting Facts about 2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxo-ethyl dihydrogen phosphate

This compound, though it may sound complex, is a fascinating example of how intricate organic chemistry can be. Its structure showcases a unique interplay of several functional groups which endow it with interesting properties and potential applications.

1. Structural Complexity

The compound features a pentacyclic framework which is notable for its rigidity and stability. This architecture allows for various interactions that may be exploited in medicinal chemistry and materials science.

2. Biochemical Relevance

The presence of a dihydrogen phosphate group suggests that this compound may play a role in biological systems, possibly influencing energy transfer or signaling pathways. Compounds like these can be analogs to nucleotides or other biologically active phosphates.

3. Potential Pharmacological Uses

Interestingly, the incorporation of fluorine in organic compounds often enhances their metabolic stability and biological activity. This could suggest potential pharmacological applications, including:

  • Antiviral agents
  • Anticancer drugs
  • Inhibitors of enzyme activity

4. Synthesis Challenges

Due to its intricate multi-cyclic and functional group architecture, synthesizing this compound can pose significant challenges. Chemists often have to employ advanced techniques, including:

  • Multi-step synthesis
  • Protecting group strategies
  • Advanced coupling reactions

As a result, this compound serves as a captivating study subject not only for its potential applications but also for the innovative synthetic strategies it necessitates.

5. A Compound with a Story

Each complex molecule, including this one, often has a unique history that may include its discovery, synthesis challenges, and eventual applications. **Studying compounds like this one helps students and researchers appreciate the beauty and complexity inherent in organic chemistry.**


Synonyms
A3XWK6919F
989-96-8
Triamcinolone Acetonide Phosphoric Acid
TRIAMCINOLONE ACETONIDE 21-DIHYDROGEN PHOSPHATE
9-Fluoro-11beta,21-dihydroxy-16alpha,17-(isopropylidenedioxy)pregna-1,4-diene-3,20-dione 21-(dihydrogen phosphate)
UNII-A3XWK6919F
Triamcinolone acetonide 21-(dihydrogen phosphate)
EINECS 213-587-5
CHEMBL2111162
DTXSID80912995
TRIAMCINOLONE ACETONIDE 21-PHOSPHATE
Q27273586
2-(4b-Fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH,8H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6b-yl)-2-oxoethyl dihydrogen phosphate
PREGNA-1,4-DIENE-3,20-DIONE, 9-FLUORO-11-HYDROXY-16,17-((1-METHYLETHYLIDENE)BIS(OXY))-21-(PHOSPHONOOXY)-, (11.BETA.,16.ALPHA.)-