5-hydroxy-l-tryptophan
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
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)
MSDS
- Language:English Provider:ACROS
- Language:English Provider:SigmaAldrich
- Language:English Provider:ALFA
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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