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Estrone

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Identification
Molecular formula
C18H22O2
CAS number
53-16-7
IUPAC name
(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
State
State

At room temperature, estrone is typically found as a solid due to its relatively high melting point.

Melting point (Celsius)
258.00
Melting point (Kelvin)
531.15
Boiling point (Celsius)
389.97
Boiling point (Kelvin)
663.12
General information
Molecular weight
270.37g/mol
Molar mass
270.3660g/mol
Density
1.2300g/cm3
Appearence

Estrone typically appears as a white to off-white crystalline solid. It may appear as a powder and is often odorless.

Comment on solubility

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

The compound (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one (C18H22O2) exhibits interesting solubility characteristics. Solubility can significantly depend on the compound's structure and functional groups. Here are key points regarding its solubility:

  • Polar vs Nonpolar: The presence of the hydroxy (-OH) group suggests that this compound may exhibit some polar characteristics, potentially leading to solubility in polar solvents such as water, although the overall hydrophobic (nonpolar) nature due to its hydrocarbon framework may limit this.
  • Organic Solvents: It is likely to be more soluble in organic solvents (e.g., ethanol, methanol, and chloroform) than in water due to its hydrophobic regions.
  • Hydration and Interaction: The solubility could be influenced by hydrogen bonding with water, although its large hydrocarbon structure could impede full solubility in aqueous environments.
  • Concentration Factors: Higher concentrations may affect solubility behavior, causing potential precipitation in mixed solvents.

Ultimately, the solubility of this compound is an engaging subject, as it reflects the balance between polar and nonpolar characteristics. In practical applications, this might be pivotal for its use in formulations requiring specific solubility profiles. Overall, while the compound may dissolve in selected solvents, it may not be readily soluble in water, posing interesting challenges and opportunities for its use in different fields.

Interesting facts

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

This compound is a fascinating example of the complex world of steroid chemistry, showcasing the intricate relationships between structure and biological function. Steroids are pivotal in many biological processes, including hormone regulation, which makes understanding their structures essential for pharmacology and biotechnology.

  • Biological Significance: Its unique stereochemistry contributes to its interaction with steroid receptors, influencing various physiological responses.
  • Potential Uses: Due to its steroid-like structure, this compound may exhibit properties useful in therapeutic applications, including anti-inflammatory and anabolic effects.
  • Synthesis: The synthetic pathways to construct such multi-cyclic compounds often involve advanced methods in organic chemistry, such as total synthesis techniques that are a hallmark of medicinal chemistry.
  • Chirality: This compound exemplifies chirality, with multiple stereocenters that may result in different biological activities or potencies based on their stereochemical configuration.

The structure also reveals a fusion of multiple ring systems, characteristic of natural products derived from terrestrial and marine sources. Such complex molecules often offer a rich field of study for chemists interested in understanding how minor structural variations can lead to significant differences in properties and functions. As one might say in the field, "the devil is in the details," emphasizing the importance of meticulousness in research and synthesis.

In conclusion, compounds like (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one are not just chemical entities; they are windows into the complexities of life and provide the foundation for much of modern medicinal chemistry. Understanding such compounds can lead to the development of new drugs and therapeutic strategies.

Synonyms
Dehydroepiandrosterone
DHEA
PRASTERONE
53-43-0
Dehydroisoandrosterone
Androstenolone
trans-Dehydroandrosterone
Diandrone
Psicosterone
Diandron
3beta-hydroxyandrost-5-en-17-one
Prestara
17-Hormoforin
17-Chetovis
Andrestenol
Intrarosa
Prasterona
5-Dehydroepiandrosterone
Siscelar plus
3-beta-Hydroxy-5-androsten-17-one
Dehydro-epi-androsterone
5,6-Didehydroisoandrosterone
Prasteronum
Vaginorm
(+)-Dehydroisoandrosterone
5,6-Dehydroisoandrosterone
Caswell No. 051F
dehydroepiandrosterone (dhea)
Epiandrosterone, 5-dehydro-
5,6-Dehydroisoandrostorone
Biolaif
CCRIS 3277
3beta-hydroxy-5-androsten-17-one
(3-beta)-3-Hydroxyandrost-5-en-17-one
EM-760
GL 701
Astenile
Deandros
5-Androsten-3beta-ol-17-one
EPA Pesticide Chemical Code 126510
Androst-5-en-17-one, 3-hydroxy-, (3beta)-
Prasteronum [INN-Latin]
Prasterona [INN-Spanish]
DEHYDROISOANDOSTERONE
NSC 9896
NSC-9896
EINECS 200-175-5
dehydroepiandosterone
UNII-459AG36T1B
BRN 2058110
Androst-5-en-17-one, 3-beta-hydroxy-
DTXSID4020379
CHEBI:28689
dehydroepiandrostenedione
NSC9896
459AG36T1B
3-beta-hydroxyandrost-5-en-17-one
Androst-5-en-17-one, 3-hydroxy-, (3.beta.)-
Androst-5-en-17-one, 3beta-hydroxy-
(3beta)-3-hydroxyandrost-5-en-17-one
CHEMBL90593
DTXCID40379
(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
D5-Androsten-3beta-ol-17-one
Androst-5-ene-3beta-ol-17-one
EC 200-175-5
Androst-5-en-17-one, 3-hydroxy-, (3-beta)-
4-08-00-00994 (Beilstein Handbook Reference)
3beta-Hydroxy-D5-androsten-17-one
Dehydro Epiandrosterone
Prasteronum (INN-Latin)
Prasterona (INN-Spanish)
PRASTERONE (MART.)
PRASTERONE [MART.]
(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one
AND
Prasterone [INN]
Fidelin
CAS-53-43-0
SMR000059075
Androst-5-en-17-one, 3.beta.-hydroxy-
SR-01000075815
Prasterone [USAN:INN]
Dehydro Epiandrosterone (1.0 mg/mL in Acetonitrile)
5-Androsten-3.beta.-ol-17-one
Anastar
Inflabloc
Aslera
Fidelin T
Androst-5-en-17-one, 3-hydroxy-, (3b)-
DHEA; Prasterone
GL701
NCGC00093802-04
NCGC00093802-06
Biolaif (TN)
5 Androsten 3 beta hydroxy 17 one
5-Androsten-3-beta-hydroxy-17-one
MFCD00003613
5-dehydro-Epiandrosterone
Prasterone (USAN/INN)
trans-de-hydroandrosterone
PRASTERONE [USAN]
bmse000665
Androsten-3beta-ol-17-one
PRASTERONE [WHO-DD]
BIDD:PXR0080
Lopac0_000368
SCHEMBL24156
MLS001066350
MLS001333231
MLS001333232
MLS001424274
5-Androsten-3B-ol-17-one
D5-Androsten-3b-ol-17-one
GTPL2370
Androst-5-ene-3b-ol-17-one
PRASTERONE [ORANGE BOOK]
3b-Hydroxyandrost-5-en-17-one
5-Androsten-3-beta-ol-17-one
BCPE00002
A14AA07
G03XX01
3b-Hydroxy-D5-androsten-17-one
3beta-Hyroxyandrost-5-en-17-one
BCPP000260
DEHYDROEPIANDROSTERONE [MI]
EL-10
HMS2052P11
HMS2090C04
HMS2232K11
IM 28
trans-Dehydroandrosterone, >=99%
3-beta-hydroxy-5-androsten-17-on
BCP02453
IPL-1001
3beta-hydroxy-androst-5-en-17-one
3beta-Hydroxyandrost-5-ene-17-one
Tox21_111222
Tox21_201996
Tox21_302761
BDBM50223368
CMC_13435
Delta5-androsten-3-beta-ol-17-one
DL-373
GL-701
LMST02020021
PB-007
s2604
DEHYDROEPIANDROSTERONE [VANDF]
3.beta.-Hydroxyandrost-5-en-17-one
5-Androsten-3beta-ol-17-one; DHEA
AKOS007930299
AKOS015951378
Tox21_111222_1
BCP9000602
CCG-101190
CS-1667
DB01708
FD12003
GS-0906
IP-1001
NC00440
SH-K-04828
NCGC00093802-09
NCGC00256412-01
NCGC00259545-01
(1S,5S,11S,15S,2R,10R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0<2,7>.0<11,15> ]heptadec-7-en-14-one
(3beta)-3-Hydroxyandrost-5-ene-17-one
AC-28716
HY-14650
NCI60_042215
Prasterone (DHEA; Dehydroepiandrosterone)
(3beta)-3-hydroxy-Androst-5-en-17-one
D0044
EU-0100368
NS00000508
Androst-5-en-17-one, 3beta-hydroxy- (8CI)
C01227
D 4000
D-0340
D08409
(3alpha,8alpha)-3-hydroxyandrost-5-en-17-one
AB00375810-06
AB00375810_09
Dehydroepiandrosterone (DHEA), 1mg/ml in Methanol
Q408376
SR-01000075815-1
SR-01000075815-4
BRD-K41256143-001-12-7
(3beta,16alpha)-3,16-dihydroxy-androst-5-en-17-one
Androst-5-en-17-one, 3-hydroxy-, (3beta)- (9CI)
1A9D2040-240C-427D-ADE4-0CB700B785CB
Prasterone (DHEA; Dehydroepiandrosterone) 1.0 mg/ml in Acetonitrile
(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one
(3S,8R,10R,13S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one
105597-37-3
200-175-5
Dehydroepiandrosterone; trans-Dehydroandrosterone; Prasterone; 5-Androsten-3beta-ol-17-one; DHEA