Indole-3-carbaldehyde
Chemical compound
From Wikipedia, the free encyclopedia
Indole-3-carbaldehyde (I3A), also known as indole-3-aldehyde and 3-formylindole, is a metabolite of dietary L-tryptophan which is synthesized by human gastrointestinal bacteria, particularly species of the Lactobacillus genus.[2][3] I3A is a biologically active metabolite which acts as a receptor agonist at the aryl hydrocarbon receptor in intestinal immune cells, in turn stimulating the production of interleukin-22 which facilitates mucosal reactivity.[4][3][2]
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| Names | |
|---|---|
| IUPAC name
1H-Indole-3-carbaldehyde | |
| Other names
3-Formylindole; Indole-3-carboxaldehyde; Indole-3-aldehyde | |
| Identifiers | |
3D model (JSmol) |
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| 5-21-08-00246 | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.006.969 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C9H7NO | |
| Molar mass | 145.161 g·mol−1 |
| Melting point | 198 °C (388 °F; 471 K) |
| Structure | |
| Orthorhombic | |
| Pca21 | |
Lattice volume (V) |
710.3 |
Formula units (Z) |
4 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis in humans and cellular effects
Tryptophan metabolism by human gut microbiota ()
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Chemistry
Indole-3-carbaldehyde has reactivity typical of aromatic aldehydes. It can is easily oxidized to indole-3-carboxylic acid. It condenses with nitromethane in a Henry reaction to give 3-nitrovinyl indole.
Antifungal properties
Indole-3-carbaldehyde has antifungal properties, and partially accounts for the protection from chytridiomycosis seen in amphibian species which carry Janthinobacterium lividum on their skin.[8]