Tryptophol
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IUPAC name
2-(1H-Indol-3-yl)ethanol
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3D model (Jmol)
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| ChemSpider | |
| ECHA InfoCard | 100.007.632 |
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PubChem CID
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| Properties | |
| C10H11NO | |
| Molar mass | 161.20 g·mol−1 |
| Melting point | 59 °C (138 °F; 332 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Tryptophol is an aromatic alcohol that induces sleep in humans. It is formed in the liver after disulfiram treatment. It is also produced by the trypanosomal parasite in sleeping sickness.
It is also found in wine as a secondary product of alcoholic fermentation. It was first described by Felix Ehrlich in 1912.
Tryptophol can be found in Pinus sylvestris needles or seeds.
It is produced by the trypanosomal parasite (Trypanosoma brucei) in sleeping sickness (African trypanosomiasis).
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 is also an autoantibiotic produced by the fungus Candida albicans.
It can also be isolated from the marine sponge Ircinia spiculosa.
It was 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.
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Wikipedia