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Dexamethasone acetate

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Identification
Molecular formula
C24H31FO6
CAS number
1177-87-3
IUPAC name
[2-[(8S,9R,10S,11S,13S,14S,16R,17S)-16-acetoxy-9-fluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] acetate
State
State

At room temperature, dexamethasone acetate is in a solid state, existing as a white to off-white crystalline powder.

Melting point (Celsius)
239.00
Melting point (Kelvin)
512.15
Boiling point (Celsius)
486.00
Boiling point (Kelvin)
759.15
General information
Molecular weight
462.52g/mol
Molar mass
462.5170g/mol
Density
1.3000g/cm3
Appearence

Dexamethasone acetate is typically observed as a white to off-white crystalline powder. It is sparingly soluble in water but more soluble in ethanol and methanol.

Comment on solubility

Solubility of the compound

The compound 2-[(8S,9R,10S,11S,13S,14S,16R,17S)-16-acetoxy-9-fluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl acetate, with the chemical formula C24H31FO6, displays unique solubility characteristics that are influenced by its complex structure.

Solubility Characteristics:

  • Polar vs. Nonpolar: With multiple hydroxyl (–OH) groups present, the compound exhibits a degree of polarity, which can enhance its solubility in polar solvents such as water.
  • Solvent Interaction: The presence of acetoxy groups contributes to potential interactions with various solvents, facilitating solubility in organic solvents such as ethanol and methanol.
  • Concentration Dependence: The solubility might vary significantly with temperature and concentration, with higher temperatures typically increasing solubility in most solvents.
  • pH Sensitivity: Given the acidic nature of the functional groups, the solubility can be affected by the pH of the solution, making it crucial to consider when dissolving the compound.

Understanding the solubility of this compound is essential for applications in pharmaceuticals and chemical synthesis, as it directly affects bioavailability and interaction with biological systems. As a general guideline, one may observe that compounds with similar structural features tend to have comparable solubility profiles. Therefore, engaging in solubility testing across a range of solvents is vital for accurately predicting interactions in practical use.

Interesting facts

Interesting Facts about the Compound

The compound 2-[(8S,9R,10S,11S,13S,14S,16R,17S)-16-acetoxy-9-fluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopentaphenanthren-17-yl]-2-oxo-ethyl acetate is quite a fascinating molecule with significant implications in medicinal chemistry.

Structure and Functional Groups

This compound includes several important functional groups, which contribute to its reactivity and biological activity:

  • Fluoro group: The presence of fluorine adds to the compound's potential bioactivity, often influencing pharmacokinetics.
  • Hydroxyl groups: These can participate in hydrogen bonding, enhancing solubility in biological systems.
  • Acetoxy group: This functional group can serve as a prodrug moiety, possibly modulating the compound’s pharmacological properties.

Biological Relevance

The complexity of the compound’s structure suggests a potential role in medicinal applications, particularly in oncology and steroid hormone therapies. Here are some insights:

  • This structure may resemble natural steroid hormones, hinting at its possibility of interacting with steroid receptors.
  • Compounds with similar configurations have been studied for their effects on cancer cells, targeting specific signaling pathways.

Synthesis and Research

Researchers are intrigued by the synthetic routes that can yield this compound. The following points highlight the synthesis challenges and interests:

  • Multi-step synthesis: The intricate nature of this molecule requires careful step-by-step synthesis, which may lead to valuable learning in organic synthesis techniques.
  • Targeted modifications: The ability to modify various functional groups could provide insights into structure-activity relationships.

In summary, the 2-[(8S,9R,10S,11S,13S,14S,16R,17S)-16-acetoxy-9-fluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopentaphenanthren-17-yl]-2-oxo-ethyl acetate is not just another molecule; it embodies the complexities and potentials that excite researchers in the fields of chemical synthesis and medicinal chemistry.

Synonyms
TRIAMCINOLONE DIACETATE
67-78-7
Aristocort Forte
Triamcinolone 16,21-diacetate
Tedarol
Aristocort Parenterals
Orion
Aristocort diacetate forte
Aristocort Forte Parenteral
Aristocort diacetate
Kenacourt
357RP
EINECS 200-669-0
UNII-A73MM2Q32P
A73MM2Q32P
CHEBI:9669
DTXSID0048713
NSC-757356
16alpha-Hydroxy-9alpha-fluoroprednisolone diacetate
9-alpha-Fluoro-16-alpha-hydroxyprednisolone diacetate
9-Fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione 16,21-diacetate
delta1,9alpha-Fluoro-16alpha-hydroxyhydrocortisone diacetate
DTXCID3028639
delta11,16alpha-Hydroxy-9alpha-fluorohydrocortisone diacetate
Triamcinolone diacetate [USP:JAN]
16alpha,21-Diacetoxy-9alpha-fluoro-11beta,17alpha-dihydroxy-1,4-pregnadiene-3,20-dione
9-Fluoro-11-beta,16-alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione 16,21-diacetate
NSC 757356
Pregna-1,4-diene-3,20-dione, 16,21-bis(acetyloxy)-9-fluoro-11,17-dihydroxy-, (11beta,16alpha)-
NCGC00159320-03
Pregna-1,4-diene-2,20-dione, 9-fluoro-11-beta,16-alpha,17,21-tetrahydroxy-, 16,21-diacetate
Triamcinolone diacetate (USP:JAN)
TRIAMCINOLONE DIACETATE (MART.)
TRIAMCINOLONE DIACETATE [MART.]
CAS-67-78-7
TRIAMCINOLONE DIACETATE (USP-RS)
TRIAMCINOLONE DIACETATE [USP-RS]
Triamcinolone diacetate [JAN]
TRIAMCINOLONE IMPURITY A (EP IMPURITY)
TRIAMCINOLONE IMPURITY A [EP IMPURITY]
TRIAMCINOLONE DIACETATE (USP MONOGRAPH)
TRIAMCINOLONE DIACETATE [USP MONOGRAPH]
Triamcinolone 16-alpha,21-di(acetate)
8357RP
SCHEMBL12549
Aristocort Forte; Aristocort Forte Parenteral; Aristocort Parenterals
CHEMBL1200449
XGMPVBXKDAHORN-RBWIMXSLSA-N
Triamcinolone diacetate (JAN/USP)
Tox21_113119
BDBM50247986
MFCD00056462
AKOS025402044
Tox21_113119_1
AC-3522
FT65195
TRIAMCINOLONE DIACETATE [VANDF]
TRIAMCINOLONE DIACETATE [WHO-DD]
NCGC00159320-02
NCGC00159320-04
[2-[(8S,9R,10S,11S,13S,14S,16R,17S)-16-acetyloxy-9-fluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
T3676
TRIAMCINOLONE 16,21-DIACETATE [MI]
TRIAMCINOLONE DIACETATE [ORANGE BOOK]
C08184
D00984
Q27108462
9alpha-Fluoro-16alpha-hydroxyprednisolone 16,21-diacetate
Triamcinolone diacetate, United States Pharmacopeia (USP) Reference Standard
(11beta,16alpha)-16,21-Bis(acetyloxy)-9-fluoro-11,17-dihydroxypregna-1,4-diene-3,20-dione
200-669-0
9alpha-Fluoro-11beta,16alpha,17alpha,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,21-diacetate