Names | |
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IUPAC name
1H-Indole-5,6-diol
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Other names
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Identifiers | |
3D model (
JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.101.149 |
EC Number |
|
KEGG | |
PubChem
CID
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|
UNII | |
CompTox Dashboard (
EPA)
|
|
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| |
Properties | |
C8H7NO2 | |
Molar mass | 149.149 g·mol−1 |
Hazards | |
GHS labelling: [1] | |
Danger | |
H302, H318, H411 | |
P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P330, P391, P501 | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
5,6-Dihydroxyindole is a chemical compound with the molecular formula C8H7NO2. It is an intermediate in the production of the biological pigment eumelanin. [2] 5,6-Dihydroxyindole is biosynthesized from L-dopachrome in a reaction catalyzed by a tyrosinase enzyme and is further converted into indole-5,6-quinone. [3] In humans, 5,6-dihydroxyindole is involved in the metabolic disorder hawkinsinuria. [3]
In some insects, 5,6-dihydroxyindole is a reactive compound that is produced as a component of defense responses and has antibacterial and antifungal activity. [4]
A laboratory synthesis of 5,6-dihydroxyindole can be accomplished starting from 3,4-dibenzyloxybenzaldehyde. [5] This compound is condensed with nitromethane in a Henry reaction, followed by nitration, reduction of the nitro groups, and hydrogenolysis of the benzyl protecting groups.
Names | |
---|---|
IUPAC name
1H-Indole-5,6-diol
| |
Other names
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.101.149 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C8H7NO2 | |
Molar mass | 149.149 g·mol−1 |
Hazards | |
GHS labelling: [1] | |
Danger | |
H302, H318, H411 | |
P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P330, P391, P501 | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
5,6-Dihydroxyindole is a chemical compound with the molecular formula C8H7NO2. It is an intermediate in the production of the biological pigment eumelanin. [2] 5,6-Dihydroxyindole is biosynthesized from L-dopachrome in a reaction catalyzed by a tyrosinase enzyme and is further converted into indole-5,6-quinone. [3] In humans, 5,6-dihydroxyindole is involved in the metabolic disorder hawkinsinuria. [3]
In some insects, 5,6-dihydroxyindole is a reactive compound that is produced as a component of defense responses and has antibacterial and antifungal activity. [4]
A laboratory synthesis of 5,6-dihydroxyindole can be accomplished starting from 3,4-dibenzyloxybenzaldehyde. [5] This compound is condensed with nitromethane in a Henry reaction, followed by nitration, reduction of the nitro groups, and hydrogenolysis of the benzyl protecting groups.