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Ethinylestradiol

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Identification
Molecular formula
C20H24O2
CAS number
57-63-6
IUPAC name
(8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
State
State

At room temperature, ethinylestradiol is in a solid state, forming a crystalline powder.

Melting point (Celsius)
183.00
Melting point (Kelvin)
456.15
Boiling point (Celsius)
451.70
Boiling point (Kelvin)
724.85
General information
Molecular weight
296.40g/mol
Molar mass
296.4030g/mol
Density
1.1654g/cm3
Appearence

Ethinylestradiol is a white to creamy white, odorless crystalline powder. It is often used in contraceptives and can appear in tablet form for medicinal purposes.

Comment on solubility

Solubility of (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

The solubility of the compound (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol with the chemical formula C20H24O2 presents interesting characteristics.

This steroid-like compound, which contains a hydroxyl (-OH) group, suggests that it may possess some level of solubility in polar solvents. Factors influencing its solubility include:

  • Hydrophilicity vs. Hydrophobicity: The presence of the hydroxyl group typically enhances solubility in water, while the extensive hydrocarbon backbone may pose challenges in fully dissolving.
  • Solvent Type: Solubility can vary widely between solvents, with organic solvents (like ethanol or dimethyl sulfoxide) potentially improving solubility compared to water.
  • Temperature Influence: Increasing the temperature often leads to enhanced solubility for many organic compounds, which could apply here as well.

In conclusion, while we can hypothesize that the compound has a degree of solubility in polar solvents due to its functional groups, empirical testing in various solvents remains essential to determine its precise solubility behavior. Therefore, it would be advantageous to conduct solubility experiments to confirm these predictions.

Interesting facts

Interesting Facts about (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

This unique compound, often found in discussions surrounding steroid structures, showcases a fascinating blend of complexity and biological significance.

Chemical Structure

The stereochemistry of this molecule is particularly notable, as evidenced by the use of several chiral centers. These stereogenic centers play a crucial role in defining the compound's reactivity and interactions within biological systems. An understanding of the stereochemistry helps elucidate how such compounds can exhibit varying levels of potency in their pharmacological effects.

Biological Relevance

This compound belongs to a class of molecules that can mimic or interact with steroid hormone pathways. Here’s why this is important:

  • Hormonal Activity: It can influence metabolic processes and may have applications in hormone therapy.
  • Research Applications: Such compounds are often studied for their potential use in treating various conditions including hormonal imbalances and certain cancers.
  • Natural Occurrence: Similar structures are frequently found in nature, often isolated from plant or animal sources.

Potential Applications

With its unique structure, this compound may open doors to numerous pharmaceutical applications:

  • Drug Development: Compounds with similar structures are commonly explored in drug discovery, aiming to develop novel therapeutics.
  • Study of Metabolism: Understanding how this molecule interacts in biological systems can provide insight into metabolic pathways.

Quote from the Field

As one expert in the field noted, “The intricate designs of steroid molecules not only illustrate the beauty of chemistry but also the potential for discovering life-saving treatments through structural modifications.”

In conclusion, (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol represents a superb subject of study for both chemists and biologists interested in the intersection of structure and function in biological systems.

Synonyms
LYNESTRENOL
52-76-6
Linestrenol
Ethinylestrenol
Lynoestrenol
Ethynylestrenol
Orgametril
Orgametrol
Endometril
Exlution
Exlutona
Orgametil
Exluton
3-Desoxynorlutin
Exluten
Ethynloestrenol
Lynstranol
Lynenol
Ethinyloestranol
Ethinyl oestrenol
NSC-37725
Linestrenolo
Lynestrenolum
Linestrenolo [DCIT]
Org 485-50
IND 1006
17alpha-Ethynylestrenol
17-alpha-Ethynylestrenol
17-alpha-Ethynyloestrenol
Linestrenol [INN-Spanish]
Lynestrenolum [INN-Latin]
CCRIS 9093
EINECS 200-151-4
19-Nor-17alpha-pregn-4-en-20-yn-17-ol
N2Z8ALG4U5
NSC 37725
Estr-4-en-17beta-ol, 17-ethynyl-
19-Norpregn-4-en-20-yn-17-ol, (17alpha)-
17-alpha-Ethynylestr-4-en-17-beta-ol
delta4-17alpha-Ethinylestren-17beta-ol
17-alpha-Ethynyloestr-4-en-17-beta-ol
DTXSID4021478
HSDB 7899
17-alpha-Ethinyl-17-beta-hydroxyestr-4-ene
17-alpha-Ethinyl-17-beta-hydroxyoestr-4-ene
Lynestrenol [USAN:INN:BAN:JAN]
NSC37725
LYNESTRENOL [MI]
17-alpha-Ethynil-delta-4-estrene-17-beta-ol
(17-alpha)-19-Norpregn-4-en-20-yn-17-ol
19-Norpregn-4-en-20-yn-17-ol, (17a)-
LYNESTRENOL [INN]
LYNESTRENOL [JAN]
LYNESTRENOL [USAN]
17.alpha.-Ethynylestrenol
delta(sup 4)-17-alpha-Ethinylestren-17-beta-ol
delta(sup 4)-17-alpha-Ethinyloestren-17-beta-ol
19-norpregn-4-en-20-yn-17alpha-ol
19-Norpregn-4-en-20-yn-17-ol, (17.alpha.)-
LYNESTRENOL [MART.]
LYNESTRENOL [USP-RS]
LYNESTRENOL [WHO-DD]
CHEBI:31790
19-Nor-17-alpha-pregn-4-en-20-yn-17-ol
19-Nor-17.alpha.-pregn-4-en-20-yn-17-ol
LYNESTRENOL [EP MONOGRAPH]
19 Norpregn-4-en-20-yn-17-ol, (17alpha)-
DTXCID501474457
(8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
Estr-4-en-17.beta.-ol, 17-ethynyl-
Linesterol
Linestrenol (INN-Spanish)
Lynestrenolum (INN-Latin)
LYNESTRENOL (MART.)
.DELTA.4-17.alpha.-Ethinylestren-17.beta.-ol
LYNESTRENOL (USP-RS)
19 NORPREGN-4-EN-20-YN-17-OL, (17.ALPHA.)-
LYNESTRENOL (EP MONOGRAPH)
Lynoestrenol [Progestins]
UNII-N2Z8ALG4U5
Exlutena
Ethynyloestrenol
Exlution(a)
CAS-52-76-6
NCGC00016233-01
Prestwick_533
MFCD00051135
Prestwick0_000095
Prestwick1_000095
Prestwick2_000095
Prestwick3_000095
Lynestrenol (JAN/USAN)
SCHEMBL37816
BSPBio_000050
SPBio_001989
17-Ethynylestr-4-en-17-ol
BPBio1_000056
CHEMBL2107431
G03AC02
G03DC03
HMS1568C12
HMS2095C12
HMS3712C12
(1R,3aS,3bR,9aR,9bS,11aS)-1-ethynyl-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-ol
BCP04136
NSC73879
Tox21_110319
Tox21_301969
LMST02030127
NSC-73879
s4883
AKOS024462708
Tox21_110319_1
19-Nor-4-pregnen-20-yn-17beta-ol
CCG-220095
DB12474
FL35098
NCGC00179676-01
NCGC00179676-03
NCGC00255262-01
L0246
NS00003323
(17alpha)-19-Norpregn-4-en-20-yn-17-ol
C75475
D01580
19-Nor-17alpha-pregn-4-en-20-yn-17-ol (8CI)
Q2071071
BRD-K39707084-001-04-1
BRD-K39707084-001-05-8
200-151-4