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Norethisterone

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Identification
Molecular formula
C20H26O2
CAS number
68-22-4
IUPAC name
(8S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
State
State

At room temperature, norethisterone is a solid substance.

Melting point (Celsius)
203.00
Melting point (Kelvin)
476.15
Boiling point (Celsius)
321.50
Boiling point (Kelvin)
594.65
General information
Molecular weight
298.42g/mol
Molar mass
298.4270g/mol
Density
1.1290g/cm3
Appearence

Norethisterone typically appears as a white to off-white crystalline powder. It is often micronized to improve its solubility in formulations.

Comment on solubility

Solubility of (8S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

The solubility of a compound can often dictate its utility in various chemical and pharmaceutical applications. For the compound (8S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one, solubility characteristics can be inferred based on its structural complexity and the functional groups present.

Factors Affecting Solubility

Solubility is influenced by several key factors, including:

  • Polarity: Compounds with polar functional groups typically exhibit higher solubility in polar solvents such as water.
  • Hydrophobic Regions: The presence of hydrophobic (non-polar) regions can reduce solubility in polar environments.
  • Temperature: Increasing temperature often enhances solubility for solid compounds.
  • pH Levels: Ionizable groups can affect a compound’s solubility based on the pH of the solution.

Predicted Solubility

Given the hydrophobic cyclopenta[a]phenanthren core and the presence of various substituents, we can deduce:

  • It may exhibit moderate solubility in organic solvents such as ethanol or acetone.
  • Its solubility in water is likely to be low due to the large non-polar hydrocarbon framework.

In conclusion, while precise solubility data may require empirical measurement, it is reasonable to suggest that this compound will manifest limited solubility in polar solvents, aligning with the general behavior of similarly structured organic compounds. As always, conducting actual solubility tests is essential for any practical applications.

Interesting facts

Interesting Facts about (8S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

This complex steroid compound, often referred to in studies related to medicinal chemistry, exhibits intriguing structural and functional characteristics. Here are some interesting aspects:

  • Steroid Backbone: This compound has a steroid-like structure, which is significant since steroids play vital roles in biological systems, including hormone production and cell membrane stability.
  • Potential Biological Activities: Compounds with similar structures have been researched for their potential anti-inflammatory, anti-tumor, and anabolic properties, making them valuable in pharmaceutical development.
  • Stereochemistry: The distinct stereochemical configuration (noted by the 'S' and 'R' designations) is crucial since the orientation of atoms can influence how the molecule interacts with biological receptors, determining its biological efficacy and safety profile.
  • Ethynyl Group: The presence of the ethynyl group in the structure is of particular interest, as it can enhance the compound's binding affinity to targets and improve its metabolic stability.
  • Hydroxyl Functionality: The hydroxyl group contributes to the compound's solubility and reactivity, which can affect its bioavailability and overall effectiveness in medicinal applications.

As a scientist or chemistry student, studying such complex compounds fosters greater understanding of structure-activity relationships (SAR) that are crucial in drug discovery. It's fascinating to observe how slight variations in structure can lead to significant changes in biological activity, illustrating one of the core principles of organic chemistry: small changes make a big difference.


Moreover, research into compounds like this can lead to the development of novel therapeutic agents, showcasing the importance of chemistry in advancing human health and understanding biological processes.

Synonyms
Gestrinone
16320-04-0
Dimetriose
Ethylnorgestrienone
Gestrinona
R-2323
Gestrinonum
RU 2323
R 2323
Ru-2323
A-46745
DTXSID4023094
(8S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
1421533RCM
A 46 745
13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregna-4,9,11-trien-20-yn-3-one
18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17alpha)-
DTXCID603094
A-46-745
Pregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-18,19-dinor-, (17alpha)-
(10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo(8.7.0.0^(2,7).0^(11,15))heptadeca-1,6,16-trien-5-one
(10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6,16-trien-5-one
(8S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta(a)phenanthren-3-one
R2323
G03XA02
Nemestran
Dimetrose
Tridomose
Gestrigone
CHEBI:89642
NCGC00167457-01
Gestrinone (1mg/ml in Acetonitrile)
Gestrinonum [INN-Latin]
Gestrinona [INN-Spanish]
CAS-16320-04-0
A 46745
BRN 5610726
Gestrinone [USAN:INN:BAN]
UNII-1421533RCM
Gestrinone (Standard)
GESTRINONE [MI]
13-Ethyl-17-alpha-ethinyl-17-hydroxygon-4,9,11-trien-3-one
GESTRINONE [INN]
GESTRINONE [JAN]
Gestrinone (USAN/INN)
GESTRINONE [USAN]
13-beta-Ethyl-17-alpha-ethinyl-17-hydroxy-gona-4,9,11-triene-3-one
GESTRINONE [MART.]
GESTRINONE [WHO-DD]
SCHEMBL217651
CHEMBL1868702
BJJXHLWLUDYTGC-ANULTFPQSA-N
HMS2089K16
HMS3715A15
MSK10950
Tox21_112461
BDBM50423515
AKOS015894932
Tox21_112461_1
CCG-220967
CS-6362
DB11619
HY-101405R
18,19-Dinor-17-alpha-pregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-
18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17-alpha)-
18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17.alpha.)-
NCGC00167457-02
FG156783
HY-101405
G0436
NS00098763
D04317
D90768
AB01275442-01
SR-01000872705
Q3761406
SR-01000872705-1
BRD-K97472745-001-01-8
13-Ethyl-17a-ethynyl-17b-hydroxygona-4,9,11-trien-3-one
(17a)-13-ethyl-17-hydroxy-18,19-Dinorpregna-4,9,11-trien-20-yn-3-one
13-ethyl-17-hydroxy-18,19-Dinor-17a-pregna-4,9,11-trien-20-yn-3-one
13-ethyl-17alpha-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one
(17alpha)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one
PREGNA-4,9,11-TRIEN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-18,19-DINOR-, (17.ALPHA.)-