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Indirubin

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Identification
Molecular formula
C16H10N2O2
CAS number
479-41-4
IUPAC name
3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one
State
State

At room temperature, indirubin is typically found in a solid state.

Melting point (Celsius)
298.00
Melting point (Kelvin)
571.15
Boiling point (Celsius)
583.15
Boiling point (Kelvin)
856.30
General information
Molecular weight
262.27g/mol
Molar mass
262.2680g/mol
Density
1.4800g/cm3
Appearence

Indirubin appears as a reddish to purple solid. It is known for its deep color and is sometimes used as a dye.

Comment on solubility

Solubility Analysis of 3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one

The solubility of 3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one can be described as both fascinating and complex due to its intricate molecular structure. Here are some key points regarding its solubility characteristics:

  • Polar vs. Nonpolar Solubility: The presence of multiple hydroxyl groups within the structure suggests that this compound may exhibit good solubility in polar solvents, such as water or alcohols, due to hydrogen bonding capabilities.
  • Hydrophobic Regions: Despite its polar characteristics, the indole moieties introduce hydrophobic regions that may impede solubility in strictly polar environments, leading to varying solubility across different solvents.
  • pH Dependency: The solubility may also change with pH variations. The hydroxyl groups could become protonated or deprotonated under different pH conditions, subsequently affecting solubility.
  • Temperature Influence: Like many organic compounds, an increase in temperature could enhance solubility, allowing greater interaction with solvents, especially in organic solutions.

In summary, while 3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one demonstrates the potential for solubility in polar solvents, its actual solubility is influenced by a mix of structural factors, solvent characteristics, pH, and temperature conditions. Understanding these interactions is essential for applications in biochemical contexts and further chemical explorations.

Interesting facts

Exploring 3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one

This fascinating compound, often abbreviated in research contexts, belongs to a class of polycyclic compounds that capture the interest of chemists and biochemists alike due to their unique structural features and potential applications. Here are some intriguing aspects that make it stand out:

  • Complex Structure: The compound boasts a highly intricate architecture involving multiple aromatic rings, which contributes to its interesting reactivity and potential biological activity.
  • Biological Significance: Compounds with similar structures are often investigated for their medicinal properties, including antioxidant and antitumor activities. They may play a role in combating diseases through various pathways.
  • Indole Derivatives: The inclusion of indole rings is particularly noteworthy; these rings are well-known for their ability to intercalate with DNA and influence biological functions. This suggests that the compound could interact with cellular mechanisms.
  • Research Applications: Because of its complex nature, this compound serves as a significant scaffold in drug design. Researchers are exploring its potential to serve as a starting point for the development of new therapeutic agents.

Furthermore, the study of such compounds offers valuable insights into the synthesis of natural products and the design of new molecules with enhanced properties.
As a quote often said in scientific circles: “Great discoveries often involve the unexpected.” Given the wide range of applications and the ongoing research, 3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one is definitely a compound to keep an eye on in future studies!

Synonyms
Violacein
548-54-9
QJH0DSQ3SG
2-INDOLINONE, 3-(2-(5-HYDROXYINDOL-3-YL)-5-OXO-2-PYRROLIN-4-YLIDENE)-
(E)-3-(5-(5-Hydroxy-1H-indol-3-yl)-2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene)indolin-2-one
(3E)-3-[5-(5-hydroxy-1H-indol-3-yl)-2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene]-1,3-dihydro-2H-indol-2-one
UNII-QJH0DSQ3SG
BRN 0049923
(3Z)-violacein
VIOLACEIN [MI]
3-(2-(5-Hydroxyindol-3-yl)-5-oxo-2-pyrrolin-4-ylidene)-2-indolinone
4-26-00-00715 (Beilstein Handbook Reference)
SCHEMBL151999
CHEMBL1652263
SCHEMBL15263185
SCHEMBL24332448
CHEBI:131914
DTXSID001028415
AAA54854
Oxindole, 3-(2-(5-hydroxyindol-3-yl)-5-oxo-2-pyrrolin-4-ylidene)-
AKOS040754806
Violacein from Janthinobacterium lividum
(3E)-3-(1,2-dihydro-5-(5-hydroxy-1H-indol-3-yl)-2-oxo-3H-pyrrol-3-ylidene)-1,3-dihydro-2H-indol-2-one
DA-59016
HY-119809
CS-0078057
NS00123417
C21136
Q4013798
Q27225295
3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one
3-(5-(5-Hydroxy-1H-indol-3-yl)-2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene)indolin-2-one
2H-INDOL-2-ONE, 3-(1,2-DIHYDRO-5-(5-HYDROXY-1H-INDOL-3-YL)-2-OXO-3H-PYRROL-3-YLIDENE)-1,3-DIHYDRO-, (3E)-
3-[1,2-dihydro-5-(5-hydroxy-1h-indol-3-yl)-2-oxo-3h-pyrrol-3-ylidene]-1,3-dihydro-2h-indol-2-one
774154-34-6
Violacein; 3-(1,2-dihydro-5-(5-hydroxy-1H-indole-3-yl)-2-oxo-3H-pyrrol-3-ylidene)-1,3-dihydro-2H-indole-2-one