Skip to main content

Spirolactone

ADVERTISEMENT
Identification
Molecular formula
C23H32O3N2
CAS number
52-01-7
IUPAC name
(3S,8S,9S,10R,13S,14S,16R,17S)-17-acetyl-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-16-carbonitrile
State
State

At room temperature, spirolactone is typically found in a solid state. It is stable under normal conditions and should be stored away from excessive heat and moisture.

Melting point (Celsius)
134.00
Melting point (Kelvin)
407.15
Boiling point (Celsius)
351.70
Boiling point (Kelvin)
624.85
General information
Molecular weight
416.58g/mol
Molar mass
416.5770g/mol
Density
1.2000g/cm3
Appearence

Spirolactone appears as a white to off-white crystalline powder. It has no discernible odor and is often used in its powdered form in various applications.

Comment on solubility

Solubility Characteristics

The compound (3S,8S,9S,10R,13S,14S,16R,17S)-17-acetyl-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-16-carbonitrile possesses unique solubility traits influenced by its complex structure. Understanding the solubility of this compound is crucial in various applications, such as pharmaceuticals and organic synthesis.

Solubility Insights

Key factors affecting solubility include:

  • Molecular Structure: The presence of multiple rings and functional groups like hydroxy (-OH) and carbonitrile (-CN) significantly impacts its solubility profile.
  • Polarity: The balance of polar and non-polar components in the molecule can dictate solubility in polar solvents (e.g., water) versus non-polar solvents (e.g., hexane).
  • Temperature: As is common with many organic compounds, increasing the temperature typically enhances solubility.

Generally, compounds with similar functional groups will experience different solubility behaviors based on their intramolecular and intermolecular interactions:

  • Hydroxyl groups often lead to increased solubility in polar solvents due to hydrogen bonding.
  • The carbonitrile may provide limited solubility in non-polar environments, as it can form dipole interactions.

In conclusion, the solubility of this compound is a result of intricate structural features that necessitate further study to fully understand its behavior in various solvents and conditions. Exploring these aspects can open doors to effective applications and better utilization of its potential.

Interesting facts

Interesting Facts about (3S,8S,9S,10R,13S,14S,16R,17S)-17-acetyl-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-16-carbonitrile

This complex organic compound, often categorized within the realm of steroids, presents a fascinating case study in structural chemistry. Here are some intriguing aspects:

  • Steroid Structure: The compound's structure is derived from a steroid framework, which is characterized by its four fused hydrocarbon rings. Such structures are essential in biochemistry, as they form the basis of many natural hormones.
  • Functional Groups: The presence of multiple functional groups, including a hydroxy (-OH) group and an acetyl (-C(=O)CH₃) group, showcases the compound's potential reactivity and application. The carbonitrile group (-C≡N) enhances its chemical versatility, making it a target for various organic reactions.
  • Chirality: This compound features several chiral centers, indicated by the S and R designations. Chirality is vital in medicinal chemistry as even slight variations in stereochemistry can significantly affect biological activity.
  • Potential Applications: The structure suggests potential use in pharmaceuticals. Compounds with similar frameworks are often investigated for their roles in modulating biological processes, particularly in hormonal pathways.
  • Historical Context: The study of such complex organic molecules can be traced back to early chemists who explored natural products. Understanding their synthesis and properties has paved the way for advances in drug design and development.

In summary, the analysis of this compound opens doors to numerous research opportunities within organic chemistry and pharmaceuticals. Its intricate structure not only provides insights into the realm of steroids but also emphasizes the importance of stereochemistry and functional groups in developing new therapeutic agents.

Synonyms
PREGNENOLONE CARBONITRILE
Pregnenolone-16alpha-carbonitrile
Pregnenolone 16alpha-carbonitrile
5-Pregnen-3beta-ol-20-one-16alpha-carbonitrile
CCRIS 9224
CHEBI:35591
BA9WH84QAJ
Pregnenolone 16 alpha Carbonitrile
(3S,8S,9S,10R,13S,14S,16R,17S)-17-acetyl-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-16-carbonitrile
DTXSID7037262
16alpha-carbonitrile, pregnenolone
Pregnenolone 16 alpha-Carbonitrile
DTXCID5017262
Pregn-5-ene-16-carbonitrile, 3-hydroxy-20-oxo-, (3beta,16alpha)-
Pregn-5-ene-16-carbonitrile, 3-hydroxy-20-oxo-, (3.beta.,16.alpha.)-
SC4674
3beta-hydroxy-20-oxopregn-5-ene-16alpha-carbonitrile
SC-4674
5-PREGNEN-3.BETA.-OL-20-ONE-16.ALPHA.-CARBONITRILE
(3beta,16alpha)-3-hydroxy-20-oxopregn-5-ene-16-carbonitrile
(3.BETA.,16.ALPHA.)-3-HYDROXY-20-OXOPREGN-5-ENE-16-CARBONITRILE
Carbonitrile, Pregnenolone
(3S,8S,9S,10R,13S,14S,16R,17S)-17-acetyl-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthrene-16-carbonitrile
16 alpha-Carbonitrile, Pregnenolone
1434-54-4
pregnenolone-carbonitrile
PCN
3beta-Hydroxy-20-oxo-5-pregnene-16alpha-carbonitrile
MLS000069563
Pregnenolone 16|A-carbonitrile
SMR000058819
Opera_ID_595
Spectrum5_001981
UNII-BA9WH84QAJ
5-Pregnen-3|A-ol-20-one-16|A-carbonitrile
BIDD:PXR0018
BSPBio_001063
Pregnenolone 16alpha-carbonite
GTPL2762
SCHEMBL1012160
CHEMBL1400945
VSBHRRMYCDQLJF-ZDNYCOCVSA-N
HMS1792E05
HMS1990E05
HMS2234D18
HMS3403E05
Tox21_303525
BDBM50248018
MFCD00079212
AKOS027381467
NCGC00023220-03
NCGC00023220-04
NCGC00023220-05
NCGC00023220-06
NCGC00023220-07
NCGC00023220-08
NCGC00257247-01
DA-57029
FP168503
MS-25223
CAS-1434-54-4
HY-131723
CS-0139744
G12567
SR-01000000148
Q7239909
SR-01000000148-3
5-Pregnen-3 beta -ol-20-one-16 alpha -carbonitrile
BRD-K39356024-001-02-4
5-Pregnen-3beta-ol-20-one-16alpha-carbonitrile, >=97%