Tryptophol Chemical Properties

Melting point:

56-59 °C(lit.)

Boiling point:

174 °C (2.02527 mmHg)

Density 

1.0840 (rough estimate)

refractive index 

1.5200 (estimate)

Flash point:

255 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

methanol: 0.1 g/mL, clear

pka

15.16±0.10(Predicted)

form 

Crystalline Mass, Crystals, Flakes or Powder

color 

Off-white to brown

Water Solubility 

10 g/L (20 ºC)

Merck 

14,9798

BRN 

125553

InChIKey

MBBOMCVGYCRMEA-UHFFFAOYSA-N

LogP

1.280 (est)

CAS DataBase Reference

526-55-6(CAS DataBase Reference)

NIST Chemistry Reference

1H-indole-3-ethanol(526-55-6)

EPA Substance Registry System

1H-Indole-3-ethanol (526-55-6)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

RTECS 

KL3685000

F 

8

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29339990

Toxicity

LD50 intraperitoneal in mouse: 351mg/kg

MSDS

• Language:English Provider:3-(2-Hydroxyethyl)indole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Tryptophol Usage And Synthesis

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: An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.

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.]

Tryptophol(526-55-6)Related Product Information

• Indole-3-acetic acid
• Oxindole
• Hydroxyethyl starch
• Ethanol
• Indole-3-butyric acid
• Indole
• Methyl 2-hydroxyethyl cellulose
• 2-(2-Aminoethylamino)ethanol
• PIPERACETAZINE (250 MG)
• Hydroxyethyl Cellulose
• Indometacin
• Sodium isethionate
• 2-(METHYLSULFONYL)ETHANOL
• TRYPTAMINE HYDROCHLORIDE
• Tryptamine
• 5-BENZYLOXYINDOLE-3-ACETIC ACID
• 5-METHYLINDOLE-3-ACETIC ACID
• METHYL 3-INDOLYLACETATE