| Identification | More | [Name]
L-5-Hydroxytryptophan | [CAS]
4350-09-8 | [Synonyms]
2-AMINO-3-(5-HYDROXY-1H-INDOL-3-YL)PROPIONIC ACID
5-HTP
5-HYDROXY-L-TRP-OH
(-)-5-HYDROXY-L-TRYPTOPHAN
5-HYDROXY-L-TRYPTOPHAN
5-HYDROXY-TRP-OH
5-HYDROXYTRYPTOPHAN
C5-HYDROXY-L-TRYPTOPHAN
H-5-HYDROXY-TRP-OH
H-TRP(5-OH)-OH
L-2-AMINO-3-(5-HYDROXYINDOLYL)PROPIONIC ACID
L-5-HTP
L-5-HYDROXYTRYPTOPHAN
L-5-HYDROXYTRYPTOPHAN HYDRATE
OXITRIPTAN
(S)-2-AMINO-3-(5-HYDROXY-1H-INDOL-3-YL)-PROPIONIC ACID
5-hydroxy-l-tryptopha
pretonine
5-Hydroxy-L-tryptophan, Free Acid
Griffonia seed | [EINECS(EC#)]
224-411-1 | [Molecular Formula]
C11H12N2O3 | [MDL Number]
MFCD00064341 | [Molecular Weight]
220.22 | [MOL File]
4350-09-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to pale grey powder | [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 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]
4350-09-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R65:Harmful: May cause lung damage if swallowed.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R20/21:Harmful by inhalation and in contact with skin . | [Safety Statements ]
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [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 |
| Hazard Information | Back Directory | [General Description]
Colorless to pale pink crystals. | [Reactivity Profile]
L-5-HYDROXYTRYPTOPHAN(4350-09-8) reacts with bases. . | [Air & Water Reactions]
This compound is sensitive to air. Slightly water soluble . | [Fire Hazard]
Flash point data for this compound are not available, however, L-5-HYDROXYTRYPTOPHAN is probably combustible. | [Chemical Properties]
white to pale grey powder | [Uses]
5-Hydroxy-L-Tryptophan is a hydroxylated metabolite of L-Tryptophan | [Uses]
A labelled metabolite of Tryptophan | [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. | [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.] |
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