L-5-Hydroxytryptophan Chemical Properties

Melting point:

270 °C (dec.) (lit.)

alpha 

-32.5 º (c=1,H2O on dry basis)

Boiling point:

361.16°C (rough estimate)

Density 

0.902 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4850(lit.)

Flash point:

175 °F

storage temp. 

2-8°C

solubility 

H₂O: 10 mg/mL

form 

solid

pka

2.22±0.10(Predicted)

color 

white

optical activity

[α]22/D 30°, c = 1 in H2O

Water Solubility 

Slightly soluble

Merck 

14,4847

BRN 

88200

LogP

-0.140 (est)

CAS DataBase Reference

4350-09-8(CAS DataBase Reference)

EPA Substance Registry System

L-5-Hydroxytryptophan (4350-09-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-65-20/21/22-20/21

Safety Statements 

36-26

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

YN7110000

F 

3-10

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29339990

MSDS

• Language:English Provider:L-5-Hydroxytryptophan
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

L-5-Hydroxytryptophan Usage And Synthesis

Chemical Properties

white to pale grey powder

Uses

A labelled metabolite of Tryptophan

Uses

5-Hydroxy-L-Tryptophan is a hydroxylated metabolite of L-Tryptophan

Uses

5-Hydroxy-L-tryptophan has been used:

• to inject experimental mice for serotonin detection
• as a precursor of 5-hydroxytryptamine and injected in pregnant mice and neonatal rats for vital neutral red staining of lung slices
• as a standard in citrate-acetate buffer for its use in high performance liquid chromatography (HPLC) analysis

Definition

ChEBI: 5-hydroxy-L-tryptophan is the L-enantiomer of 5-hydroxytryptophan. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is a 5-hydroxytryptophan, a hydroxy-L-tryptophan and a non-proteinogenic L-alpha-amino acid. It is an enantiomer of a 5-hydroxy-D-tryptophan. It is a tautomer of a 5-hydroxy-L-tryptophan zwitterion.

General Description

Colorless to pale pink crystals.

Air & Water Reactions

L-5-Hydroxytryptophan is sensitive to air. Slightly water soluble .

Reactivity Profile

L-5-Hydroxytryptophan reacts with bases. .

Fire Hazard

Flash point data for L-5-Hydroxytryptophan are not available, however, L-5-Hydroxytryptophan is probably combustible.

Trade name

Levothym (Promonta Lundbeck, Germany), Lévotonine (Panpharma, France), Oxyfan (Coli, Italy), Tript-OH (Sigma- Tai, Italy).

Biochem/physiol Actions

Hydroxylation of L-tryptophan occurs in the brain during serotonin synthesis. This is a step that controls the production of serotonin and also yields 5-hydroxy-l-tryptophan (5-HTP) as a metabolite. Thus, consumption 5-HTP, increases the serotonin level, which might result in depression, lack of sleep and severe headache.

Purification Methods

Likely impurities are 5-hydroxy-D-tryptophan and 5-benzyloxytryptophan. Crystallise 5-hydroxy-L-tryptophan under nitrogen from water by adding EtOH. Store it under nitrogen. Also dissolve it in the minimum volume of hot H2O (~0.7g in 4mL) under nitrogen (charcoal) and allowed it to crystallise at 5o. The picrolonate crystallises from H2O with m 184-186o(dec). [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2732-2737 1961, Morris & Armstrong J Org Chem 22 306 1957, Beilstein 22/14 V 278.]

L-5-Hydroxytryptophan(4350-09-8)Related Product Information

• 5-Hydroxytryptophan
• L-Tryptophan
• CHLOROPHOSPHONAZO III
• Osthole
• 2-Hydroxy-DL-tryptophan
• D-5-HYDROXYTRYPTOPHAN
• O-2-propenyl-Tyrosine
• (S)-2-Amino-3-(4-ethylphenyl)propanoic acid
• H-L-Phe(4-CH2OtBu)-OH
• (2S)-2-amino-3-(4-propoxyphenyl)propanoic acid
• 2-(Trifluoromethoxy)-L-phenylalanine
• 2-(1H-indol-3-yl)acetaldehyde
• 3-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione
• 2-(3-INDOLYLMETHYL)-L-TRYPTOPHAN
• N-Acetyl-L-tryptophan
• 3-(phenylamino)alanine
• HARMANE-1,2,3,4-TETRAHYDRO-3-CARBOXYLIC ACID
• Tryptophan Impurity 1（Tryptophan EP Impurity A）