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5-hydroxy-l-tryptophan

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5-hydroxy-l-tryptophan Basic information

Product Name:
5-hydroxy-l-tryptophan
Synonyms:
  • (S)-2-AMino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid hydrate
  • 5-HYDROXY-TRP-OH
  • 5-HYDROXY-L-TRP-OH
  • 5-HTP
  • (S)-2-AMINO-3-(5-HYDROXY-1H-INDOL-3-YL)-PROPIONIC ACID
  • C5-HYDROXY-L-TRYPTOPHAN
  • H-TRP(5-OH)-OH
  • H-5-HYDROXY-TRP-OH
CAS:
314062-44-7
MF:
C11H12N2O3
MW:
220.22
EINECS:
224-411-1
Mol File:
314062-44-7.mol
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5-hydroxy-l-tryptophan Chemical Properties

Melting point:
270 °C (dec.)(lit.)
Density 
0.902 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.4850(lit.)
Flash point:
175 °F
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
solubility 
H2O: 10 mg/mL
form 
solid
color 
white
InChI
InChI=1/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-/s3
InChIKey
LDCYZAJDBXYCGN-DJEYLCQNNA-N
SMILES
C12C=C(C=CC=1NC=C2C[C@H](N)C(=O)O)O |&1:10,r|
CAS DataBase Reference
314062-44-7(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
36
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
YN7110000
3-10

MSDS

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5-hydroxy-l-tryptophan Usage And Synthesis

Description

5-hydroxy-l-tryptophan (5-HTP) is a chemical byproduct of the protein building block L-tryptophan. It is produced commercially from the seeds of an African plant known as Griffonia simplicifolia. In vivo, it is produced from tryptophan by tryptophan hydroxylase (TPH), and its decarboxylation yields serotonin (5-hydroxytryptamine, 5-HT), a monoamine neurotransmitter involved in the modulation of mood, cognition, reward, learning, memory, sleep, and numerous other physiological processes. 5-HTP is both a drug and a natural component of some dietary supplements, and occurrence in both synthetic tryptophan and 5-HTP of toxic impurities has caused eosinophilia myalgia syndrome cases[1].

Uses

5-hydroxy-l-tryptophan is metabolized into serotonin and is thought to alleviate depression by enhancing serotonin neurotransmission. It is also used to treat fibromyalgia, insomnia, binge-eating, attention deficit disorder, and chronic headaches.

References

[1] Maffei, Massimo E. "5-Hydroxytryptophan (5-HTP): Natural Occurrence, Analysis, Biosynthesis, Biotechnology, Physiology and Toxicology." International Journal of Molecular Sciences 22.1(2021):181.

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