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17β-Hydroxyandrost-4-ene-3-one

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Identification
Molecular formula
C19H28O2
CAS number
58-22-0
IUPAC name
(5R,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
State
State
Testosterone is a solid at room temperature, typically appearing as a crystalline powder.
Melting point (Celsius)
153.00
Melting point (Kelvin)
426.15
Boiling point (Celsius)
370.80
Boiling point (Kelvin)
643.95
General information
Molecular weight
288.43g/mol
Molar mass
288.4240g/mol
Density
1.1450g/cm3
Appearence

Testosterone appears as a white to off-white crystalline powder. It is practically insoluble in water but is soluble in alcohol, chloroform, dioxane, and acetone.

Comment on solubility

Solubility Characteristics

The compound (5R,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one exhibits unique solubility properties largely influenced by its intricate molecular structure. Due to the presence of multiple functional groups and the hydrophobic hydrocarbon framework, its solubility can vary significantly.

Factors Influencing Solubility:

  • Molecular Size: The large size of the molecule may hinder solubility in polar solvents.
  • Hydrophobicity: The extensive hydrocarbon regions generally lead to poor solubility in water but better solubility in organic solvents.
  • Functional Groups: The hydroxyl (-OH) group may enhance solubility in alcohols and other polar solvents.

Generally, this compound is expected to be:

  • Insoluble in water: Due to its substantial hydrophobic character.
  • Moderately soluble in polar organic solvents: Like ethanol or methanol due to the presence of the hydroxyl group.
  • Soluble in non-polar solvents: Such as hexane or chloroform, where the hydrophobic sections of the molecule can better interact.

In conclusion, understanding the solubility of this compound is crucial for applications in various fields such as pharmaceuticals where its bioavailability could be affected by its solubility characteristics. As with many complex organic compounds, the interplay between hydrophobic and hydrophilic regions defines its interaction with solvents.

Interesting facts

Interesting Facts about (5R,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

This compound is a fascinating member of the class of steroids, which are organic compounds characterized by their unique carbon skeletons formed by four fused rings. Here are some intriguing aspects of this compound:

  • Stereochemistry: The molecule features several stereocenters, creating a complex three-dimensional structure that significantly influences its biological activity and interactions with other molecules.
  • Biological Relevance: Compounds like this one are often involved in biological systems, particularly in hormone pathways. Understanding its structure can provide insights into how it functions in the human body.
  • Applications: Due to its configuration, this compound may have potential applications in pharmaceutical development, particularly in designing drugs that mimic or inhibit natural steroid actions.
  • Research Interest: Chemists are particularly interested in this compound for synthesis and modification. The intricate arrangement of functional groups presents unique challenges and opportunities in organic synthesis.

Quote from a chemist: "The beauty of steroids lies in their structural complexity and the profound effects they can have on biological systems."

This compound illustrates the marvelous world of organic chemistry, where a slight alteration in structure can lead to dramatically different properties and functions. As research continues, discoveries about such compounds could lead to breakthroughs in medical science and chemistry.

Synonyms
5beta-Dihydrotestosterone
571-22-2
5beta-Androstan-17beta-ol-3-one
5-beta-Dht
5-beta-Dihydrotestosterone
Etiocholan-17-beta-ol-3-one
17beta-Hydroxyetiocholan-3-one
5beta,17beta-Hydroxyandrostan-3-one
17beta-hydroxy-5beta-androstan-3-one
Etiocholane-17-beta-ol-3-one
SVX1G0C5VD
NSC 15460
CHEBI:2150
17-beta-Hydroxy-5-beta-androstan-3-one
(5beta,17beta)-17-hydroxyandrostan-3-one
(5-beta,17-beta)-17-Hydroxyandrostan-3-one
(5beta,8alpha,17beta)-17-hydroxyandrostan-3-one
5.beta.-Dihydrotestosterone
5beta-Androstan-3-one, 17beta-hydroxy-
DTXSID0022488
17.beta.-Hydroxyetiocholan-3-one
5-beta-ANDROSTAN-3-ONE, 17-beta-HYDROXY-
Androstan-3-one, 17-hydroxy-, (5beta,17beta)-
17beta-hydroxy-5betaandrostan-3-one
Androstan-3-one, 17-hydroxy-, (5-beta,17-beta)-
NSC-15460
5.beta.-Androstan-17.beta.-ol-3-one
Androstan-3-one, 17-hydroxy-, (5.beta.,17.beta.)-
5-beta-Androstan-17-beta-ol-3-one
DTXCID602488
5beta-Androstan-3-one, 17beta-hydroxy-(8CI)
Androstan-3-one, 17-hydroxy-, (5beta,17beta)-(9CI)
Androstan-3-one, 17-hydroxy-, (5-beta,17-beta)-(9CI)
(5R,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
CHEMBL373357
5beta-Androstane-17beta-ol-3-one
Etiocholan-17beta-ol-3-one
etiocholan-17-beta-ol-3-one (5betaDHT)
5b-Androstane-17b-ol-3-one
5B-DIHYDROTESTOSTERONE
5beta-Androstane-17beta-ol-3-one (1.0mg/ml in Acetonitrile)
UNII-SVX1G0C5VD
MLS000563095
BIDD:ER0549
SCHEMBL619535
BDBM50410540
LMST02020069
DB07447
17 beta Hydroxy 5 beta Androstan 3 One
PD005177
SMR001215857
NS00069270
C05293
Q27096666
(1S,3aS,3bR,5aR,9aS,9bS,11aS)-1-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-7-one
(5R,8R,10S,13S,17S)-17-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one