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| | L-5-Hydroxytryptophan Basic information |
| | 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 | | pka | 2.22±0.10(Predicted) | | color | white | | Optical Rotation | [α]22/D 30°, c = 1 in H2O | | Water Solubility | Slightly soluble | | Merck | 14,4847 | | BRN | 88200 | | Major Application | pharmaceutical small molecule | | InChI | 1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1 | | InChIKey | LDCYZAJDBXYCGN-VIFPVBQESA-N | | SMILES | N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(O)=O | | LogP | -0.140 (est) | | CAS DataBase Reference | 4350-09-8(CAS DataBase Reference) | | EPA Substance Registry System | L-5-Hydroxytryptophan (4350-09-8) |
| 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 | TSCA listed | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29339990 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral |
| | 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. | | reaction suitability | reaction type: solution phase peptide synthesis | | 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 Preparation Products And Raw materials |
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