L-5-Hydroxytryptophan

L-5-Hydroxytryptophan
  • CAS No.:4350-09-8
Other grades of this product :
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.)
Fp 175 °F
storage temp. 2-8°C
solubility H2O: 10 mg/mL
form solid
pka2.22±0.10(Predicted)
color white
optical activity[α]22/D 30°, c = 1 in H2O
Water Solubility Slightly soluble
Merck 14,4847
BRN 88200
CAS DataBase Reference4350-09-8(CAS DataBase Reference)
EPA Substance Registry SystemL-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
3-10
TSCA Yes
HazardClass 6.1
PackingGroup III
HS Code 29339990
MSDS Information
ProviderLanguage
L-5-Hydroxytryptophan English
SigmaAldrich English
ACROS English
ALFA English
L-5-Hydroxytryptophan Usage And Synthesis
Chemical Propertieswhite to pale grey powder
UsesA labelled metabolite of Tryptophan
Uses5-Hydroxy-L-Tryptophan is a hydroxylated metabolite of L-Tryptophan
Uses5-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
General DescriptionColorless to pale pink crystals.
Air & Water ReactionsL-5-Hydroxytryptophan is sensitive to air. Slightly water soluble .
Reactivity ProfileL-5-Hydroxytryptophan reacts with bases. .
Fire HazardFlash point data for L-5-Hydroxytryptophan are not available, however, L-5-Hydroxytryptophan is probably combustible.
Biochem/physiol ActionsHydroxylation 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 MethodsLikely 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 Preparation Products And Raw materials
Preparation ProductsTryptamine

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