154-02-9

Basic information

• Product Name: 5-HYDROXYTRYPTOPHOL
• Synonyms: 2-(5-HYDROXY-3-INDOLYL)ETHYL ALCOHOL;5-HYDROXYTRYPTOPHOL;5-HYDROXYINDOLE-3-ETHANOL;5-hydroxy-1h-indole-3-ethano;5-hydroxy-1h-indole-3-ethanol;5-hydroxy-indole-3-ethano;hydroxytryptophol;5-hydroxytryptophol crystalline
• CAS NO: 154-02-9
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• EINECS: 205-820-4
• Product Categories: Indoles and derivatives;Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 154-02-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 111-113°?
• Boiling Point: 435.2°C at 760 mmHg
• Flash Point: 217°C
• Appearance: /
• Density: 1.356g/cm³
• Vapor Pressure: 2.42E-08mmHg at 25°C
• Refractive Index: 1.718
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.07±0.40(Predicted)
• CAS DataBase Reference: 5-HYDROXYTRYPTOPHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXYTRYPTOPHOL(154-02-9)
• EPA Substance Registry System: 5-HYDROXYTRYPTOPHOL(154-02-9)

Safety Data

• RTECS: NL8512500
• Hazardous Substances Data: 154-02-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Crystalline Powder

Uses

A metabolite of Tryptophan (T947200).

Hazard

A reproductive hazard.

Biological Activity

5-hydroxy tryptophol is a metabolite of tryptophan.tryptophan (encoded by the codon ugg) is an α-amino acid that is used in the biosynthesis of proteins. tryptophan has an α-amino group, an α-carboxylic acid group, and a side chain indole, demonstrating it as a non-polar, aromatic amino acid. tryptophan is critical in humans, but the body cannot synthesize it and therefore tryptophan must be obtained from the diet. tryptophan is also found to be a precursor to the neurotransmitters serotonin and melatonin.

in vitro

in previous studies, 5-hydroxy tryptophol was identified as a metabolite of tryptophan that was formed by the alcohol dehydrogenase-catalyzed reduction of the serotonin intermediate, 5-hydroxyindoleacetaldehyde. moreover, depending on the tissue nad/nadh ratio, the acetaldehyde intermediate could also be oxidized by aldehyde dehydrogenase to form 5-hydroxyindoleacetic acid. therefore, the ratio of 5-hydroxy tryptophol to 5-hydroxyindoleacetic acid could be used as a biomarker for recent alcohol consumption [1,2].

references

[1] yokoyama, m. t. and carlson, j.r. dissimilation of tryptophan and related indolic compounds by ruminal microorganisms in vitro. appl.microbiol. 27(3), 540-548 (1974).[2] beck, o. ,stephanson, n.,btthcer, m., et al. biomarkers to disclose recent intake of alcohol: potential of 5-hydroxytryptophol glucuronide testing using new direct uplc-tandem ms and elisa methods. alcohol & alcoholism 42(4), 321-325 (2007).

InChI:InChI=1/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2

Upstream product

• 41339-61-1 5-benzyloxy-3-(2-hydroxyethyl)indole 
• 54-16-0 5-Hydroxyindole-3-acetic acid 
• 4382-53-0 2-(5-benzyloxy-1H-indol-3-yl)acetic acid 
• 1453-97-0 5-benzyloxygramine 

Downstream Products

• 1262008-05-8 2-(5-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1H-indol-3-yl)ethanol 
• 1262007-41-9 2-(6-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid 
• 1262008-23-0 methyl 2-(6-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate 
• 1262007-23-7 2-(6-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid 
• 1262009-08-4 (S)-2-(6-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid 
• 1262009-06-2 (R)-2-(6-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid 
• 936252-91-4 2-(3-(5-(p-toluenesulfonyloxy)-1-(p-toluenesulfonyl)indolyl)ethyloxy)adenosine 
• 936252-51-6 3-(2-iodoethyl)-1-(p-toluenesulfonyl)-5-(p-toluenesulfonyloxy)indole 
• 936252-75-4 6-chloro-2-(3''-(5''-(p-toluenesulfonyloxy)-1''-(p-toluenesulfonyl)indolyl)ethyloxy)-3',4',5'-triacetyladenosine 
• 1027646-16-7 1-(p-toluenesulfonyl)-3-(p-toluenesulfonyloxyethyl)-5-(p-toluenesulfonyloxy)indole 
• 27939-38-4 C₁₆H₁₉NO₈ 

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Hypothesis: The unknown prevalence of alcohol use and misuse among aviation pilots, crewmembers and associated support personnel call for continuous improvement of methods for detecting recent alcohol use. Early detection is essential to proper treatment and prevention of potentially catastroph...detailed

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Relevant articles and documents

5-Hydroxytryptophol: a metabolite of 5-hydroxytryptamine in rats.

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SPIROCYCLIC CYCLOHEXANE DERIVATIVES

The invention relates to spirocyclic cyclohexane derivatives, to a method for the production thereof, to medicaments containing said compounds and to the utilization of spirocyclic cyclohexane derivatives for the production of medicaments.