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Levonorgestrel

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Identification
Molecular formula
C21H28O2
CAS number
797-63-7
IUPAC name
(8S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
State
State

At room temperature, levonorgestrel is a solid. It is usually found in a crystalline powder form, making it suitable for manufacturing into tablets or other dosage forms for medicinal use.

Melting point (Celsius)
206.00
Melting point (Kelvin)
479.00
Boiling point (Celsius)
487.85
Boiling point (Kelvin)
761.00
General information
Molecular weight
312.45g/mol
Molar mass
312.4460g/mol
Density
1.1200g/cm3
Appearence

Levonorgestrel appears as a white or almost white crystalline powder. It is practically odorless, and it is soluble in dichloromethane, slightly soluble in alcohol, and practically insoluble in water. This compound has a defined crystalline appearance often used in pharmaceutical preparations.

Comment on solubility

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

The solubility of the compound (8S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one is influenced by several factors, primarily its chemical structure and the presence of functional groups.

  • Hydrophobic Character: The presence of large hydrocarbon rings in the structure suggests that this compound may have a significant hydrophobic character, which often leads to poor solubility in water.
  • Presence of Functional Groups: The hydroxyl group (-OH) indicates potential for hydrogen bonding, which may enhance its solubility in polar solvents such as alcohols or dimethyl sulfoxide (DMSO).
  • Effects of Ethynyl Group: The ethynyl group (-C≡C-) introduces additional non-polar characteristics, which could further hinder solubility in aqueous environments.

In summary, this compound's solubility profile is likely characterized by:

  1. Limited solubility in water due to hydrophobic properties.
  2. Enhanced solubility in organic solvents where the compound can engage in favorable interactions.
  3. Interactions with functionalized media that can accommodate polar groups.

Overall, understanding the solubility of this compound is crucial for applications in pharmaceuticals and material science, where the solubility profile could impact its efficacy and usability.

Interesting facts

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

This unique compound is a member of the steroid-like family of chemicals, showcasing a complex structure that holds significance in various biological contexts. Here are some fascinating aspects:

  • Biological Relevance: This compound's structural features resemble those of natural steroid hormones, making it of interest in studies related to hormonal activity and metabolic processes.
  • Potential Therapeutic Uses: Compounds like this can play a role in developing therapies for conditions involving hormonal regulation, including certain types of cancers and metabolic disorders.
  • Synthetic Versatility: The presence of an ethynyl group enhances the compound's reactivity, allowing for numerous synthetic modifications. This can lead to the discovery of new derivatives with tailored biological effects.
  • Structure-Activity Relationship (SAR): Understanding how changes in the structure of this compound affect its biological activity is crucial for chemists and pharmacologists aiming to design more effective drugs.
  • Research Opportunities: The compound opens avenues for research in stereochemistry, as the specific stereochemical configuration significantly influences its biological interactions.

In the world of chemistry, compounds such as (8S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one are essential not just for their functional roles but also for what they teach us about molecular interactions and the development of future pharmaceuticals.

Get inspired and explore the potential applications and implications of such molecules!

Synonyms
NORGESTRIENONE
848-21-5
Ethynyl trienolone
Norgestrienona
Planor
Norgestrienonum
17alpha-Ethynyltrienolone
Norgestrienone [INN:DCF]
Norgestrienonum [INN-Latin]
Norgestrienona [INN-Spanish]
EINECS 212-698-6
NSC 101105
UNII-89386PYU9O
BRN 6230207
17-Hydroxy-19-nor-17alpha-pregna-4,9,11-trien-20-yn-3-one
Norgestrienone (INN)
89386PYU9O
R 2010
NORGESTRIENONE [MI]
NSC-101105
NORGESTRIENONE [INN]
NORGESTRIENONE [MART.]
NORGESTRIENONE [WHO-DD]
17-alpha-Ethynyl-17-beta-hydroxyestra-4,9,11-trien-3-one
17-Hydroxy-19-nor-17-alpha-pregna-4,9,11-trien-20-yn-3-one
DTXSID30878491
A 301
19-Nor-17-alpha-pregna-4,9,11-trien-20-yn-3-one, 17-hydroxy-
19-Nor-17alpha-pregna-4,9,11-trien-20-yn-3-one, 17-hydroxy-
19-Norpregna-4,9,11-trien-20-yn-3-one, 17-hydroxy-, (17-alpha)-
Norgestrienonum (INN-Latin)
Norgestrienona (INN-Spanish)
NORGESTRIENONE (MART.)
17-Hydroxy-19-nor-17.alpha.-pregna-4,9,11-trien-20-yn-3-one
(1R,3aS,3bS,11aS)-1-ethynyl-1-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,11aH-cyclopenta(a)phenanthren-7-one
(1R,3aS,3bS,11aS)-1-ethynyl-1-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,11aH-cyclopenta[a]phenanthren-7-one
19-Norpregna-4,9,11-trien-20-yn-3-one, 17-hydroxy-, (17alpha)-
G03AC07
DTXCID001016537
19-Nor-17alpha-pregna-4,9,11-trien-20-yn-3-one, 17-hydroxy-(8CI)
19-Norpregna-4,9,11-trien-20-yn-3-one, 17-hydroxy-, (17-alpha)-(9CI)
212-698-6
(8S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
A301
NSC 101105; Ogyline; Planor; R 2010; RU 2010
SCHEMBL146644
CHEMBL1908319
CHEBI:135231
AKOS040753312
DB13563
DA-56257
HY-111302
CS-0034886
NS00042024
D07220
Q7051184