Indole-3-acetaldehyde

Indole-3-acetaldehyde
Names
Preferred IUPAC name
(1H-Indol-3-yl)acetaldehyde
Other names
Indoleacetaldehyde; 1H-Indole-3-acetaldehyde; 2-(Indol-3-yl)acetaldehyde; Indole-3-acetaldehyde; Indoleacetaldehyde; 1H-Indol-3-ylacetaldehyde; 2-(3-Indolyl)acetaldehyde; Indol-3-ylacetaldehyde; Tryptaldehyde; IAL; IAAL
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH C001655
UNII
  • InChI=1S/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2
    Key: WHOOUMGHGSPMGR-UHFFFAOYSA-N
  • O=CCC1=CNC2=CC=CC=C12
Properties
C10H9NO
Molar mass 159.188 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Indole-3-acetaldehyde (IAL) belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. It is a metabolite of tryptamine formed by monoamine oxidase (MAO).

Indole-3-acetaldehyde is a substrate for retina-specific copper amine oxidase, aldehyde dehydrogenase X (mitochondrial), amine oxidase B, amiloride-sensitive amine oxidase, aldehyde dehydrogenase (mitochondrial), fatty aldehyde dehydrogenase, 4-trimethylaminobutyraldehyde dehydrogenase, aldehyde dehydrogenase (dimeric NADP-preferring), aldehyde dehydrogenase family 7 member A1, amine oxidase A, aldehyde dehydrogenase 1A3 and membrane copper amine oxidase.[1]

See also

References

  1. ^ Nutaratat P, Srisuk N, Arunrattiyakorn P, Limtong S (2016). "Indole-3-acetic acid biosynthetic pathways in the basidiomycetous yeast Rhodosporidium paludigenum". Arch Microbiol. 198 (5): 429–37. Bibcode:2016ArMic.198..429N. doi:10.1007/s00203-016-1202-z.

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