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5-Hydroxytryptophan

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5-Hydroxytryptophan Basic information

Product Name:
5-Hydroxytryptophan
Synonyms:
  • DL-5-HTP
  • DL-5-HYDROXYTRYPTOPHAN
  • DL-2-AMINO-3-(5-HYDROXYINDOLYL)PROPIONIC ACID
  • HYDROXYTRYPTOPHAN
  • 5-HYDROXY-DL-TRYPTOPHAN
  • 5-Hydroxytryptophan(5-HTP)
  • DL-2-Amino-3-(5-hydroxyindolyl)propionic acid, DL-5-HTP
  • 5-HTP (Griffonia Seeds P.E.)
CAS:
56-69-9
MF:
C11H12N2O3
MW:
220.22
EINECS:
200-284-8
Product Categories:
  • Inhibitors
  • Plant extracts
  • Herb extract
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • Standard extract
  • Amines
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Metabolites & Impurities
  • Pharmaceuticals
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
Mol File:
56-69-9.mol
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5-Hydroxytryptophan Chemical Properties

Melting point:
298-300°C
Boiling point:
361.16°C (rough estimate)
Density 
1.484
refractive index 
1.5200 (estimate)
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
pka
2.22±0.10(Predicted)
form 
solid
Water Solubility 
Soluble in water (4 mg/ml at 25°C), methanol.
Merck 
14,4847
BRN 
88199
InChIKey
LDCYZAJDBXYCGN-UHFFFAOYSA-N
CAS DataBase Reference
56-69-9(CAS DataBase Reference)
EPA Substance Registry System
Tryptophan, 5-hydroxy- (56-69-9)
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Safety Information

Safety Statements 
26
WGK Germany 
3
RTECS 
YN7100000
PackingGroup 
III
Hazardous Substances Data
56-69-9(Hazardous Substances Data)

MSDS

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5-Hydroxytryptophan Usage And Synthesis

Description

5-Hydroxytryptophan (5-HTP) is an aromatic amino acid naturally produced by the body from the essential amino acid L-tryptophan (LT). Produced commercially by extraction from the seeds of the African plant, Griffonia simplicifolia, 5-HTP has been used clinically for over 30 years. The clinical efficacy of 5-HTP is due to its ability to increase production of serotonin in the brain.

Chemical Properties

Off-White to Pale Beige Solid

Originator

Levotonine,Panmedica,France,1973

Uses

5-Hydroxytryptophan (5-HTP) is an intermediate in the natural synthesis of the essential amino acid, tryptophan, to serotonin. Clinical studies suggest that 5-HTP supports healthy serotonin levels. In the body, 5-HTP converts to serotonin with the enzymatic removal of a carboxyl group (COOH). Serotonin is an important neurotransmitter involved in the regulation of endocrine and brain activity responsible for emotion, appetite and sleep/wake cycles.?

Uses

A metabolite of Tryptophan. 5-Hydroxytryptophan (5-HTP) is a direct 5-hydroxytryptamine (5-HT) precursor used to assess central serotonergic function.

Application

5-hydroxytryptophan is a dietary supplement made from the seeds of the African plant Griffonia simplicifolia.
5-hydroxytryptophan has been used in alternative medicine as a possibly effective aid in treating depression or fibromyalgia.
Other uses not proven with research have included insomnia, alcohol withdrawal, headaches, premenstrual syndrome, binge-eating related to obesity, attention deficit disorder, and muscle spasms in the mouth.
5-hydroxytryptophan is often sold as an herbal supplement. There are no regulated manufacturing standards in place for many herbal compounds and some marketed supplements have been found to be contaminated with toxic metals or other drugs. Herbal/health supplements should be purchased from a reliable source to minimize the risk of contamination.

Manufacturing Process

Preparation of 5-Hydroxytryptophan: 0.4 gram palladium chloride and 1.7 grams acid-washed charcoal were suspended in 157 ml water and hydrogenated at room temperature and atmospheric pressure until no further hydrogen uptake occurred. A suspension of 14.2 grams 5- benzyloxytryptophan in 175 ml ethyl alcohol was added and the mixture hydrogenated under similar conditions. A hydrogen uptake slightly in excess of theory was obtained. The suspension was warmed for a few minutes on the steam bath and filtered hot. The filter-cake was washed with hot water (3 x 20 ml) and the filtrate evaporated to 20 ml under reduced pressure in a nitrogen atmosphere.
The resultant mass of colorless crystals was triturated with 250 ml ice-cold ethyl alcohol under hydrogen, filtered, and washed with cold ethyl alcohol (2 x 15 ml). The 5-hydroxytryptophan (6.9 grams, 69%) had MP (sealed evacuated tube) 288°C, with softening, finally melting at 249° to 247°C (decomposition). Concentration of the liquors under reduced pressure in a nitrogen atmosphere, and trituration as before, gave a second crop (0.9 gram, 9%). The combined crops (7.8 grams) were dissolved in 120 ml hot water, charcoal added, and the mixture filtered hot. The filtrate was concentrated in a nitrogen atmosphere under reduced pressure and ethyl alcohol added. The 5-hydroxytryptophan then crystallized as colorless microneedles (6.5 grams,65%), had MP (sealed evacuated tube) 290°C, with slight softening, finally melting at 295° to 297°C (decomposition).

Therapeutic Function

Antidepressant, Antiepileptic

Source

5-HTP is derived from the Griffonia simplicifolia plant. Hypo-allergenic plant fiber is derived from pine cellulose.

Mode of action

5-Hydroxytryptophan acts primarily by increasing levels of serotonin within the central nervous system. Other neurotransmitters and CNS chemicals, such as melatonin, dopamine, norepinephrine, and beta-endorphin have also been shown to increase following oral administration of 5-HTP. This ability to increase not only serotonin levels in the brain, but also dopamine and norepinephrine, allows 5-HTP to produce some significant and unique effects on brain chemistry and on serotonin-related conditions which other substances, including LT, cannot duplicate.?

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