Names | |
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IUPAC name
1H-Indole-3-carbaldehyde
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Other names
3-Formylindole; Indole-3-carboxaldehyde; Indole-3-aldehyde
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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 | |
a = 14.076, b = 5.8059, c = 8.6909[1]
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Lattice volume (V)
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710.3 |
Formula units (Z)
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4 |
Hazards | |
GHS labelling: | |
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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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]
Tryptophan metabolism by human gastrointestinal microbiota ( )
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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.
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]