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Dexamethasone

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Identification
Molecular formula
C22H29FO5
CAS number
50-02-2
IUPAC name
(8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-2,10,13-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
State
State

Dexamethasone is solid at room temperature, typically found as a crystalline powder. It is stable in air and its crystalline nature allows it to be handled as a solid substance.

Melting point (Celsius)
255.00
Melting point (Kelvin)
528.15
Boiling point (Celsius)
323.20
Boiling point (Kelvin)
596.35
General information
Molecular weight
392.46g/mol
Molar mass
392.4610g/mol
Density
1.2242g/cm3
Appearence

Dexamethasone is a white to practically white, crystalline powder. It is odorless or has a slight odor and is stable in air. It is practically insoluble in water, slightly soluble in ethanol, and soluble in chloroform.

Comment on solubility

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

The solubility of this complex organic compound is influenced by its molecular structure, which includes multiple functional groups and polycyclic systems. Understanding the solubility behavior can be essential for its applications in pharmaceuticals and materials science.

  • Polar vs. Nonpolar: Due to the presence of hydroxyl (–OH) groups, this compound exhibits a degree of polarity, which can promote solubility in polar solvents such as water or ethanol.
  • Hydrogen Bonding: The –OH functional groups enable strong hydrogen bonding interactions, potentially enhancing solubility in solvent systems capable of forming similar interactions.
  • Alkyl Chain Interactions: The trimethyl and hydroxyacetyl groups introduce nonpolar characteristics, which might limit solubility in pure water but enhance it in organic solvents such as dimethyl sulfoxide (DMSO).
  • pH Dependence: The solubility may vary with changes in pH due to the ionization of hydroxyl groups, affecting their interaction with solvents.

Overall, while the solubility profile of this compound suggests it could dissolve in a variety of solvent systems, it is crucial to consider specific conditions (temperature, solvent type, pH) for optimal dissolution. As always, experimental validation is key to accurately determining solubility parameters.

Interesting facts

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

This compound, known for its intricate structure and significant biological properties, has garnered attention in various fields of research. Here are some intriguing facts worth noting:

  • Structural Complexity: This compound features multiple chiral centers, which contributes to its unique stereochemistry. The configuration around these centers plays a crucial role in its biological activity.
  • Fluorine Substitution: The presence of a fluorine atom enhances the compound's lipophilicity, potentially improving its pharmacokinetic properties, making it more bioavailable.
  • Hydroxy and Acetyl Groups: The dihydroxy and hydroxyacetyl functional groups are believed to influence the compound's interactions with biological targets, possibly leading to novel therapeutic applications.
  • Hydrocarbon Backbone: The extensive hydrocarbon structure is indicative of its belonging to a class of compounds called steroids, which are vital in biological functions such as hormone synthesis and cellular signaling.
  • Potential Therapeutic Applications: Due to its structural attributes, this compound may show promise in areas like oncology and endocrinology, where steroids are often explored for their therapeutic effects.

As a student or researcher delving into the world of complex organic compounds like this one, understanding its synthesis and mechanistic pathways can be both challenging and rewarding. Each component, from the chiral centers to functional groups, contributes to the overall behavior of the compound, reinforcing the notion that in chemistry, the details matter.

This compound serves as a compelling example of how structural nuances can unlock significant biological activities and pave the way for future discoveries in medicinal chemistry.

Synonyms
V6Q9S11Z0T
382-59-2
2-Methyl-9alpha-fluorocortisol
2-Methyl-9-fluorohydrocortisone
2-methylfludrocortisone
UNII-V6Q9S11Z0T
DTXSID40959149
Pregn-4-ene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-2-methyl-, (11beta)-
9alpha-Fluoro-11beta,17alpha,21-trihydroxy-2-methylpregn-4-ene-3,20-dione
Pregn-4-ene-3,20-dione, 9-fluoro-11beta,17,21-trihydroxy-2-methyl-
Pregn-4-ene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-2-methyl-, (11.beta.)-
2-METHYL-9.ALPHA.-FLUOROCORTISOL
2-METHYL-9.ALPHA.-FLUOROHYDROCORTISONE
9-Fluoro-11,17,21-trihydroxy-2-methylpregn-4-ene-3,20-dione
9.ALPHA.-FLUORO-11.BETA.,17.ALPHA.,21-TRIHYDROXY-2-METHYLPREGN-4-ENE-3,20-DIONE
PREGN-4-ENE-3,20-DIONE, 9-FLUORO-11.BETA.,17,21-TRIHYDROXY-2-METHYL-