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19-Normetamorphane

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Identification
Molecular formula
C18H28O2
CAS number
638-95-9
IUPAC name
(3R,5R,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
State
State
At room temperature, the compound is present in a solid state, specifically as a crystalline powder.
Melting point (Celsius)
137.00
Melting point (Kelvin)
410.15
Boiling point (Celsius)
384.50
Boiling point (Kelvin)
657.70
General information
Molecular weight
286.42g/mol
Molar mass
286.4210g/mol
Density
1.1100g/cm3
Appearence

The compound is a white crystalline solid. It generally appears as a powder or in finely crystalline form that is odorless and has a slightly sweet taste.

Comment on solubility

Solubility of (3R,5R,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one (C18H28O2)

The solubility of the compound (3R,5R,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one is an intriguing topic due to its specific structural characteristics. While some compounds readily dissolve in water, this particular compound exhibits notably low solubility in aqueous solutions. Here are the key factors influencing its solubility:

  • Molecular Polarities: The presence of hydroxyl (-OH) groups provides some degree of polarity, which could enhance solubility in polar solvents; however, the larger hydrophobic hydrocarbons dominate.
  • Hydrophobic Characteristics: As a steroid-like structure, its substantial hydrophobic regions tend to limit its interactiveness with water, reducing overall solubility.
  • Solvent Dependence: This compound may demonstrate higher solubility in organic solvents like ethanol or chloroform compared to polar solvents.

In conclusion, the solubility of C18H28O2 can be summarized succinctly: while it possesses functional groups that may enhance solubility, the overall structure predisposes it to being sparingly soluble in water yet potentially soluble in various organic solvents. Always consider the solvent influence when evaluating similar compounds!

Interesting facts

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

This compound, often referred to in the context of steroid biology, is a fascinating substance with several noteworthy properties and applications. Here are some key points to consider:

  • Synthetic Analogue: This compound serves as a synthetic analogue of natural steroid hormones, making it a valuable tool for studying hormonal mechanisms and effects in biological systems.
  • Structural Complexity: Featuring a complex polycyclic structure, its stereochemistry is critical for its biological activity. The specific configuration at various chiral centers (indicated by R and S notations) plays a vital role in how the compound interacts with biological receptors.
  • Biological Relevance: Compounds with similar structures to this one are known to exhibit a wide range of biological activities, including anti-inflammatory, anti-cancer, and anabolic effects, which are important in medical and sports science research.
  • Research Applications: Scientists frequently study this compound to better understand steroidogenesis, signaling pathways, and the development of novel therapeutic agents. Its therapeutic potential is a key area of interest, particularly in the fields of endocrinology and oncology.
  • Pioneering Studies: Research utilizing this compound has paved the way for breakthroughs in hormone replacement therapy and the treatment of hormone-related disorders, making it a compound of considerable historical significance in medicinal chemistry.

In summary, the intricate nature of (3R,5R,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one not only highlights its potential as a drug but also exemplifies the beauty of organic chemistry in constructing compounds that can have profound impacts on health and disease.

Synonyms
etiocholanolone
53-42-9
5-Isoandrosterone
Aetiocholanolone
Etiocholan-3alpha-ol-17-one
3alpha-Hydroxy-5beta-androstan-17-one
5beta-Androsterone
Etiocholanone
5b-androsterone
3alpha-Etiocholanolone
Androsterone, (5beta)-
5 beta Androsterone
alpha-Etiocholanolone
5.beta.-Androsterone
5beta-Androstan-3alpha-ol-17-one
Androsterone, (5.beta.)-
NSC 50908
Etiocholan-3.alpha.-ol-17-one
3.alpha.-Etiocholanolone
5.beta.-Androstan-17-one, 3.alpha.-hydroxy-
NSC-50908
(3R,5R,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
Androstan-17-one, 3-hydroxy-, (3alpha,5beta)-
5beta-Androstan-17-one, 3alpha-hydroxy-
CHEMBL85799
(3alpha,5beta)-3-hydroxyandrostan-17-one
.ALPHA.-ETIOCHOLANOLONE
97CGB1M48I
3.alpha.-Hydroxy-5.beta.-androstan-17-one
3alpha-Hydroxyetiocholan-17-one
CHEBI:28195
DTXSID001018919
NSC50908
J4.146G
Androstan-17-one, 3-hydroxy-, (3a,5b)-
3-alpha-hydroxy-5-beta-androstan-17-one
3-Hydroxyandrostan-17-one-, (3.alpha.,5.beta.)-
Androstan-17-one,3-hydroxy-, (3a,5b)-
SMR000857108
3 alpha Hydroxy 5 beta Androstan 17 One
5-beta-Androsterone
5beta-Androsterone (1mg/ml in Acetonitrile)
Androstan-17-one, 3-hydroxy-, (3.alpha.,5.beta.)-
UNII-97CGB1M48I
Atiocholanolon
a-Etiocholanolone
1dbj
3a-Etiocholanolone
5.beta.-Androstan-3.alpha.-ol-17-one
(3R,5R,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta(a)phenanthren-17-one
MLS000563093
MLS001332471
MLS001332472
SCHEMBL148334
5B-Androstan-3A-ol-17-one
5b-Androstane-3a-ol-17-one
3a-Hydroxy-5b-androstane-17-one
DTXCID801476933
HMS2231A23
5beta-Androstane-3alpha-ol-17-one
BDBM50191348
LMST02020059
MFCD00064133
AKOS015895180
DB02854
FA17917
3alpha-Hydroxy-5beta-androstane-17-one
NCGC00485031-01
MS-24148
3-alpha-hydroxy-5-beta-androstane-17-one
Androstan-17-one, (3.alpha.,5.beta.)-
HY-113320
CS-0059589
NS00069543
3-Hydroxyandrostan-17-one-, (3alpha,5beta)-
C04373
G60903
5beta-Androstan-17-one, 3alpha-hydroxy-(8CI)
(3alpha,5beta,8alpha)-3-hydroxyandrostan-17-one
Q5404598
Androstan-17-one, 3-hydroxy-, (3alpha,5beta)-(9CI)
Etiocholan-3alpha-ol-17-one, VETRANAL(TM), analytical standard
(3a,5b)-3-Hydroxyandrostan-17-one;3a-Hydroxy-5b-androstan-17-one;3a-Etiocholanolone
(3R,5R,8R,10S,13S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
AE2