|Jmol-3D images||Image 1|
|Molar mass||161.20 g mol−1|
|Melting point||59 °C|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
It is found in wine or in beer (although at levels of <23 mg/L in Canadian beers as a secondary product of alcoholic fermentation (a product also known as congener) by Saccharomyces cerevisiae.
It has been first described by Felix Ehrlich in 1912. Ehrlich demonstrated that yeast attacks the natural amino acids essentially by splitting off carbon dioxide and re-placing the amino group with hydroxyl. By this reaction, tryptophan gives rise to tryptophol. Tryptophan is first deaminated to 3-indolepyruvate. It is then decarboxylated to indole acetaldehyde by indolepyruvate decarboxylase. This latter compound is transformed to tryptophol by alcohol dehydrogenase.
The unicellular alga Euglena gracilis converts exogenous trytophol to two major metabolites: tryptophol galactoside and an unknown compound (a tryptophol ester), and to minor amounts of indole-3-acetic acid, tryptophol acetate and tryptophol glucoside.
Tryptophol and its derivatives 5-hydroxytryptophol and 5-methoxytryptophol, induce sleep in mice. It induces a sleep-like state that lasts less than an hour at the 250 mg/kg dose. These compounds may play a role in physiological sleep mechanisms. It may be a functional analog of serotonin or melatonin, compounds involved in sleep regulation.
Tryptophol is a quorum sensing molecule for the yeast Saccharomyces cerevisiae. It is also found in the bloodstream of patients with chronic trypanosomiasis. For that reason, it may be a quorum sensing molecule for the trypanosome parasite.
In the case of trypanosome infection, tryptophol decreases the immune response of the host.
As it is formed in the liver after ethanol ingestion or disulfiram treatment, it is also associated with the study of alcoholism. Pyrazole and ethanol have been shown to inhibit the conversion of exogenous tryptophol to indole-3-acetic acid and to potentiate the sleep-inducing hypothermic effects of tryptophol in mice.
Precursor for synthesis of other compounds
It is used in the synthesis of the drug indoramin.
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- Pathway: tryptophan degradation VIII (to tryptophol) at BioCyc.org
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- Kosalec, Ivan; Ramić, Snježana; Jelić, Dubravko; Antolović, Roberto; Pepeljnjak, Stjepan; Kopjar, Nevenka (2011). "Assessment of Tryptophol Genotoxicity in Four Cell Lines in Vitro: A Pilot Study with Alkaline Comet Assay". Archives of Industrial Hygiene and Toxicology 62.
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- Rayle, DL; Purves, WK (1967). "Isolation and Identification of Indole-3-Ethanol (Tryptophol) from Cucumber Seedlings". Plant Physiology 42 (4): 520–524.
- Jelaska, Sibila; Magnus, Volker; Seretin, Mira; Lacan, Goran (1985). "Induction of embryogenic callus in Cucurbita pepo hypocotyl explants by indole-3-ethanol and its sugar conjugates". Physiologia Plantarum 64 (2): 237.
- "Dialkyltryptamines via Tryptophol - [www.rhodium.ws]". Erowid.org. Retrieved 2013-08-18.