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Hydrocortisone

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Identification
Molecular formula
C21H30O5
CAS number
50-23-7
IUPAC name
(8S,9S,10R,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
State
State

Hydrocortisone is typically found as a solid at room temperature. As a fine crystalline powder, it maintains its solid state under normal conditions.

Melting point (Celsius)
215.00
Melting point (Kelvin)
488.15
Boiling point (Celsius)
462.10
Boiling point (Kelvin)
735.25
General information
Molecular weight
362.46g/mol
Molar mass
362.4600g/mol
Density
1.3020g/cm3
Appearence

Hydrocortisone is a white to practically white, odorless, crystalline powder. It is highly soluble in methanol and ethanol, soluble in chloroform, sparingly soluble in acetone, and slightly soluble in water. The crystals appear as a fine, white powder, making them easily distinguishable.

Comment on solubility

Solubility of (8S,9S,10R,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

The solubility of the compound C21H30O5 can be characterized as follows:

  • Polar Solvents: The presence of the 2-hydroxyacetyl group suggests some level of polarity, which may render this compound soluble in polar solvents such as methanol and ethanol.
  • Non-Polar Solvents: Given its larger non-polar hydrocarbon structure, it may also be soluble in non-polar organic solvents like hexane and chloroform.
  • Water Solubility: Due to the hydrophobic nature of the bulk of the molecule, one might expect limited solubility in water. The overall steric hindrance and hydrophobic interactions typically prevent extensive hydrogen bonding with water molecules.

In conclusion, the solubility profile is likely complex, exhibiting varying solubility depending on the solvent's nature. As observed, compounds with a mix of polar and non-polar characteristics often display varied solubility behavior: “Like dissolves like” remains a guiding principle in predicting solubility. Scientists must consider solvent interactions versus the molecule's structural features when assessing solubility for practical applications.

Interesting facts

Interesting Facts about (8S,9S,10R,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

This complex organic compound, often associated with various biological activities, boasts a fascinating structure that contributes to its unique properties and potential applications. Here are some notable highlights:

  • Biological Relevance: This compound is noted for its presence in certain natural products, and research indicates it may play a role in biological processes, such as signaling pathways within living organisms.
  • Synthetic Versatility: The structural complexity offers chemists challenging yet rewarding synthetic routes, making it a subject of interest in organic synthesis studies.
  • Pharmacological Interest: Its unique structure might suggest potential pharmacological activities, drawing attention from medicinal chemists looking for new therapeutic agents.
  • Application in Research: This compound is often utilized as a reference material in various chemical analyses, enhancing our understanding of structure-activity relationships.

Remarkably, the specific stereochemistry (_S_ and _R_ configurations) contributes to the compound's chiral nature, leading to distinct biological behavior that can vary significantly between enantiomers. As emphasized by leading chemists, "Understanding the nuances of chiral compounds can unlock a plethora of therapeutic possibilities."
This highlights the importance of stereochemistry in pharmaceutical chemistry, making it a marvellous subject for future investigations and studies.

Overall, this compound serves as a prime example of the intricate relationship between structure and functionality in organic chemistry, prompting further exploration into its potential applications and benefits.

Synonyms
Desoxycortone
11-Deoxycorticosterone
desoxycorticosterone
Deoxycorticosterone
21-Hydroxyprogesterone
64-85-7
Cortexone
Deoxycortone
11-Desoxycorticosterone
Reichstein's substance Q
4-Pregnen-21-ol-3,20-dione
Desossicortone
Desoxicortonum
Kendall's desoxy compound B
11-Dehydroxycorticosterone
Corticosterone, 11-deoxy-
Desoxycorticosteronum
11-Deoxy Corticosterone
21-Hydroxy-4-pregnene-3,20-dione
Progesterone, 21-hydroxy-
21-HYDROXYPREGN-4-ENE-3,20-DIONE
Pregn-4-ene-3,20-dione, 21-hydroxy-
1,2(3H)-Deoxycorticosterone
Desoxicortona
Desoxycortonum
DOC
NSC 11319
Desoxycortonum [INN-Latin]
EINECS 200-596-4
Desoxicortona [INN-Spanish]
UNII-40GP35YQ49
DTXSID0045254
CHEBI:16973
40GP35YQ49
21-hydroxy-Pregn-4-ene-3,20-dione
MLS000028537
MLS001076270
DTXCID8025254
21-Hydroxy-3,20-dioxopregn-4-ene
Desoxycortone (INN)
21-Hydroxy-Delta4-pregnene-3,20-dione
SMR000058340
DESOXYCORTONE [INN]
Desoxycortonum (INN-Latin)
Desoxicortona (INN-Spanish)
(8S,9S,10R,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
DESOXYCORTONE (MART.)
DESOXYCORTONE [MART.]
Desossicortone [DCIT]
[4-14C]-11-deoxycorticosterone
NSC-11319
1CA
11 Decorticosterone
11-Decorticosterone
21 Hydroxyprogesterone
11-deoxy-Corticosterone
Desoxycortone [INN:BAN]
Reichstein Q
Desoxycorticosteron
'Reichstein Q'
CAS-64-85-7
NCGC00016292-01
11-Dcortic
21 Hydroxy 4 pregnene 3,20 dione
MFCD00003661
DOCA (Salt/Mix)
acAtate de dAsoxycortone
Opera_ID_581
21-hydroxy-Progesterone
Prestwick0_000957
Prestwick1_000957
Prestwick2_000957
Prestwick3_000957
Kendalls desoxy compound B
bmse000535
SCHEMBL4065
CHEMBL1498
BSPBio_000954
Deoxycorticosterone (Standard)
SPBio_003103
DESOXYCORTONE [WHO-DD]
BDBM8582
BPBio1_001050
GTPL2871
DEOXYCORTICOSTERONE [MI]
hydroxy-4-pregnene-3,20-dione
H02AA02
4-pregnene-3,20-dione-21-ol
HMS1570P16
HMS2097P16
HMS2235G07
HMS3714P16
D4-Pregnene-21-ol-3,20-dione
DESOXYCORTICOSTERONE [VANDF]
Tox21_110356
Tox21_302402
CMC_13409
LMST02030087
Delta4-Pregnene-21-ol-3,20-dione
21-Hydroxy-D4-pregnane-3,20-dione
21-Hydroxy-D4-pregnene-3,20-dione
AKOS005111365
Tox21_110356_1
CCG-220957
FD21043
HY-113414R
21-Hydroxypregn-4-ene-3,20-dione #
NCGC00021304-03
NCGC00021304-05
NCGC00256184-01
21-Hydroxy-Delta4-pregnane-3,20-dione
21-Hydroxyprogesterone, >=97% (HPLC)
AS-77189
HY-113414
AB00490029
CS-0059402
NS00005226
(14beta)-21-hydroxypregn-4-ene-3,20-dione
C03205
D07792
G60883
Q948846
SR-01000003106
21-HYDROXY-.DELTA.4-PREGNENE-3,20-DIONE
SR-01000003106-2
BRD-K98521173-001-03-8
BRD-K98521173-001-19-4
BD5D7BC9-0CD8-404E-9BA0-F670962012F8
4-Pregnen-21-ol-3,20-dione;21-Hydroxyprogesterone;Cortexone
4-PREGNEN-21-OL-3,20-DIONE; DOC; 21-HYDROXYPROGESTERONE
(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
(8S,10R,13S,17S)-17-(2-Hydroxy-acetyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
200-596-4