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Indirubin

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

At room temperature, Indirubin is a solid. It exists in a stable crystalline form under standard conditions of temperature and pressure.

Melting point (Celsius)
289.00
Melting point (Kelvin)
562.00
Boiling point (Celsius)
784.00
Boiling point (Kelvin)
1 057.00
General information
Molecular weight
262.27g/mol
Molar mass
262.2680g/mol
Density
1.3347g/cm3
Appearence

Indirubin appears as a red-brown crystalline powder. It is known for its striking color, which makes it easily identifiable among other compounds. It is not hygroscopic and maintains its crystalline structure at room temperature.

Comment on solubility

Solubility of 2-(3-hydroxy-1H-indol-2-yl)indol-3-one

The solubility of the compound 2-(3-hydroxy-1H-indol-2-yl)indol-3-one can vary significantly based on its environment. Here are some key points regarding its solubility:

  • Polarity: Being an indole derivative with hydroxyl groups, this compound is expected to exhibit moderate polarity, which influences its solubility in various solvents.
  • Solvent Interaction: It is likely to be soluble in polar organic solvents such as methanol and ethanol due to the potential for hydrogen bonding.
  • Water Solubility: Its solubility in water may be limited, considering that many indole derivatives display low solubility in aqueous solutions.
  • Effect of pH: The solubility can also be influenced by the pH of the solution, particularly due to the presence of the hydroxyl group, which may ionize under certain conditions.
  • Temperature Dependency: Like many organic compounds, an increase in temperature might enhance solubility in organic solvents.

In summary, while 2-(3-hydroxy-1H-indol-2-yl)indol-3-one may show variable solubility, it predominantly derives its enhanced solubility characteristics from its polar functional groups and the influence of solvent properties.

Interesting facts

Interesting Facts about 2-(3-hydroxy-1H-indol-2-yl)indol-3-one

2-(3-hydroxy-1H-indol-2-yl)indol-3-one, often referred to in scientific circles due to its intriguing structure and properties, serves as a fascinating example in the realm of organic compounds. Here are some interesting aspects to ponder:

  • Complex Structure: This compound features a dual indole structure, which is known for its rich chemistry and biological significance, particularly in natural products and pharmaceuticals.
  • Biological Activity: The presence of hydroxyl (-OH) groups and the indole moiety implies potential roles in biological activities, including anti-inflammatory, antioxidant, and anticancer properties. Such features make it a candidate for further medicinal exploration.
  • Intermolecular Interactions: The structural characteristics of this compound suggest that it can engage in important π-π stacking interactions, crucial in drug design and molecular recognition processes.
  • Versatile Synthesis: The synthetic pathways leading to this compound often involve innovative approaches, making it a subject of current research focusing on synthetic methodologies in organic chemistry.
  • Research Implications: As a compound derived from indole, it contributes to the broader understanding of indole derivatives, which have widespread applications, ranging from dyes to pharmaceuticals.

In summary, 2-(3-hydroxy-1H-indol-2-yl)indol-3-one illustrates the beauty and complexity of organic compounds, making it a vital topic for further study and exploration in both academia and industry.

Synonyms
INDIGO
482-89-3
Indigo Blue
Vat blue 1
Cystoceva
Diindogen
Vulcafix Blue R
Indigo Pure BASF
Indigo Ciba
Indigo Synthetic
Synthetic Indigo
Indigo Powder W
Vulcafor Blue A
Indigo J
Indigo N
Indigo P
Vynamon Blue A
Indigo VS
Indigo Ciba SL
Indigo NAC
Indigo PLN
Indigo NACCO
Mitsui Indigo Pure
C.I. Vat Blue 1
Mitsui Indigo Paste
Synthetic Indigo TS
Vulcol Fast Blue GL
Lithosol Deep Blue B
Vulcanosine Dark Blue L
D&C Blue No. 6
Blue No. 201
D and C Blue No. 6
Lithosol deep blue V
3H-Indol-3-one, 2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-
Indigo Pure BASF Powder K
Monolite Fast Navy Blue BV
11669 Blue
Modr kypova 1
Indigo (VAN)
CI Vat Blue 1
CI 73000
(2,2'-Biindoline)-3,3'-dione
Modr Kypova 1 [Czech]
C.I. 73000
delta2,2'-Bipseudoindoxyl
D & C Blue No. 6
Indigo [HPUS]
Indigo [HSDB]
Indigo [MI]
NCI-C61392
2-(3-hydroxy-1H-indol-2-yl)indol-3-one
CCRIS 4379
D+C Blue No. 6
HSDB 4372
delta(sup 2,2')-Bipseudoindoxyl
AO201
NSC 8645
NSC-8645
EINECS 207-586-9
Indigotin (natural)
BRN 0088275
D&C Blue No. 6 [II]
1G5BK41P4F
DTXSID3026279
AI3-09080
C.I.73000
(2E)-2-(3-oxo-1H-indol-2-ylidene)-1H-indol-3-one
2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one
INDIGO [WHO-DD]
(delta2,2'(3H,3'H)-Biindole)-3,3'-dione
(delta2,2'-Biindoline)-3,3'-dione
2,2'-Biindole-3,3'(1H,1'H)-dione
AO201 [INCI]
64784-13-0
(delta(sup 2,2')-Biindoline)-3,3'-dione
COHYTHOBJLSHDF-BUHFOSPRSA-
EC 207-586-9
CI 73000 [INCI]
DTXCID101022739
2-(1,3-Dihydro-3-oxo-2H-indazol-2-ylidene)-1,2-dihydro-3H-indol-3-one
5-24-08-00503 (Beilstein Handbook Reference)
(.DELTA.(SUP 2,2')-BIINDOLINE)-3,3'-DIONE
D&C BLUE NO. 6 (II)
[delta2,2'-Biindoline]-3,3'-dione
[DELTA2,2'(3H,3'H)-BIINDOLE]-3,3'-DIONE
VULCAFIX BLUE
PIGMENT INDIGO V
NATURAL BLUE 1
INDIGO [HOC]
delta2,2'Bipseudoindoxyl
D+C BLUE NO 6
D AND C BLUE NO 6
NATURAL BLUE INDIGOTIN
C BLUE 22
BLUE NO 201
MITSUI INDIGO PURE EXN
C.I. NATURAL BLUE 1
(2,2'Biindoline)3,3'dione
(delta2,2'Biindoline)3,3'dione
DELTA(2,2')-BIPSEUDOINDOXYL
DELTA(SUP 2,2')BIPSEUDOINDOXYL
(delta(sup 2,2')Biindoline)3,3'dione
(delta2,2'Biindoline)3,3'dione (8CI)
(delta2,2'-Biindoline)-3,3'-dione (8CI)
(DELTA(2,2')-BIINDOLINE)-3,3'-DIONE
(DELTA(2,2'(3H,3'H))-BIINDOLE)-3,3'-DIONE
2(1,3Dihydro3oxo2Hindol2ylidene)1,2dihydro3Hindol3one
2(1,3Dihydro3oxo2Hindazol2ylidene)1,2dihydro3Hindol3one
3HIndol3one, 2(1,3dihydro3oxo2Hindol2ylidene)1,2dihydro
2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-o-ne
inchi=1/c16h10n2o2/c19-15-9-5-1-3-7-11(9)17-13(15)14-16(20)10-6-2-4-8-12(10)18-14/h1-8,17-18h/b14-13+
Indigotin
Indigo (synthetic)
indigo dye
indigo blue (powder)
Indigo,natural
12626-73-2
68651-46-7
MFCD00005722
C.I Vat blue 1
D&C Blue No.6
D&C Blue 6
D And C Blue Number 6
CHEMBL599552
.DELTA.2,2'-Bipseudoindoxyl
[2,2'-Biindolinylidene]-3,3'-dione
NCGC00163355-01
(Z)-[2,2'-Biindolinylidene]-3,3'-dione
Indigo (Technical Grade)
1H,1'H-[2,2']Biindolylidene-3,3'-dione
Indigo Naturalis
Indigo (dye)
2001554-70-5
CAS-482-89-3
SMR000857361
(E)-[2,2'-Biindolinylidene]-3,3'-dione
(2E)-2,2'-biindole-3,3'(1H,1'H)-dione
UNII-1G5BK41P4F
Indigoblau
cis-indigo
indigo B
Indigo, synthetic
D & C blue No 6
[.DELTA.2,3'-dione
(2E)-2-(3-oxoindolin-2-ylidene)indolin-3-one
SCHEMBL42280
SCHEMBL56085
MLS001335921
MLS001335922
CHEMBL35479
MEGxp0_001924
Indigo (C.I. 73000)
SCHEMBL23064865
ACon1_002192
Indigofera Tinctoria Leaf Extract
NSC8645
CHEBI:177687
COHYTHOBJLSHDF-BUHFOSPRSA-N
COHYTHOBJLSHDF-UHFFFAOYSA-N
QQILFGKZUJYXGS-UHFFFAOYSA-N
BCP26169
HY-N0335
Tox21_112052
Tox21_202545
BDBM50310357
s3876
2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-o- ne
AKOS015900171
AKOS015955899
Indigo, synthetic, Dye content 95 %
Tox21_112052_1
AC-8002
CCG-267072
FI39298
CID 5354391
NCGC00091633-01
NCGC00163355-02
NCGC00163355-03
NCGC00163355-04
NCGC00163355-05
NCGC00260094-01
DA-74475
PD100504
SY108978
[(D)(2,2')-Biindoline]-3,3'-dione
2-(3-oxoindolin-2-ylidene)indolin-3-one
(.DELTA.2,2'-Biindoline)-3,3'-dione
[.DELTA.2,3'H)-Biindole]-3,3'-dione
CS-0008896
I0212
NS00002041
NS00009769
NS00076533
VAT BLUE 1 (INDIGO C.I. 73000)
Q422662
SR-01000941903
(.DELTA.2,2'(3H,3'H)-Biindole)-3,3'-dione
Indigo, EuropePharmacopoeia (EP) Reference Standard
SR-01000941903-2
2-(3-oxo-2,3-dihydro-1h-indol-2-ylidene)-2,3-dihydro-1h-indol-3-one
(2,2 inverted exclamation mark -biindoline)-3,3 inverted exclamation mark -dione