Indole

Synthesis

An example: Internal dehydration of o -aminophenylethanal, a nucleophilic attack reaction of nitrogen on the carbonyl carbon:

Natural derivatives

Tryptophan

β -indolylalanine

Essential amino acid. Occurs at 1% in human proteins. Is precursor of serotonin (neurotransmitter that regulates our mood, our eating behavior and prepares us to sleep) which is formed from tryptophan by - Hydroxylation (1) - Decarboxylation (2)

Serotonin

Scatole

3-methylindole

Formed from tryptophan in the putrefaction of proteins. Is primarily responsible for the unpleasant odor of feces, whereas at low concentration, it contributes to the pleasant scent of jasmine and orange blossom!.

Auxin

β -indolylethanoc acid

Is formed from tryptophan. This is a multiple-acting plant growth hormone (bud, root, leaf blade, phototropism).

Indigo

Indigo is a blue-violet dye.

The precursor of indigo, the Indican is extracted from certain plants such as Indigofera Tintoria

Preparation: 1) Hydrolysis of indican:

2) Oxidation of indoxyl

An ancient method practiced in India was to ferment the leaves of Indigofera tinctoria containing indican in basins dug into the moist soil, then collect the yellowish liquid containing indoxyl and beat to oxidize by the air. Indigo formed was deposited at the bottom.

Application: