Chemical Properties
3-(2-Hydroxyethyl)indole [526-55-6], tryptophol, C10H11NO, Mr 161.20, mp 59 ℃, bp 174 ℃, (2 kPa) forms colorless prisms or flakes that are readily soluble in methanol, ethanol, diethyl ether, chloroform, and acetone, soluble in benzene, and slightly soluble in water. It is produced by reacting methyl-1H-indole-3-acetate with lithium aluminum hydride, or through reduction of methyl-1H-indole-3-glyoxylate with sodium borohydride. The antihypertensive Indoramin is produced from tryptophol.
Uses
Tryptophol is a metabolite formed in the liver after disulfiram treatment that induces sleep in humans. It is also a secondary product of alcoholic fermentation.
Uses
Reactant for preparation of:
- Inhibitors of the C-terminal domain of RNA polymerase II and their antitumor activities
- Anti-HIV-1 agents
- Inhibitors of Protein-Protein Interactions
- Partial agonists of the serotonin 5-HT1A receptor
- Growth hormone secretagogues
- Vascular endothelial growth factor (VEGF) inhibitors
- A2B adenosine receptor ligands
- Potential detoxification inhibitors of the crucifer phytoalexin brassinin
- Inhibitors of interleukine 6
- Dual binding site acetylcholinesterase inhibitors
Definition
ChEBI: Tryptophol is an indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2. It has a role as an auxin, a Saccharomyces cerevisiae metabolite and a plant metabolite.
Synthesis Reference(s)
Canadian Journal of Chemistry, 42, p. 485, 1964
DOI: 10.1139/v64-070
Purification Methods
Crystallise it from diethyl ether/pet ether, *C6H6, *C6H6/pet ether. The picrate has m 100-101o (from *C6H6). [Beilstein 21 I 218, 21 II 49, 21 III/IV 788, 21/3 V 61.]
References
[1] Shen, Tao, et al. “Direct Tryptophols Synthesis from 2-Vinylanilines and Alkynes via C≡C Triple Bond Cleavage and Dioxygen Activation.”
Journal of the American Chemical Society, 138 40, 2016, pp. 13147–50,
https://doi.org/10.1021/jacs.6b08094.
[2] Palmieri, Alessandro, and Marino Petrini. “Tryptophol and Derivatives: Natural Occurrence and Applications to the Synthesis of Bioactive Compounds.”
Natural Product Reports, 36 3, 2019, p. Pages 490-530,
https://doi.org/10.1039/c8np00032h.
