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ChemicalBook >> CAS DataBase List >>5-Hydroxytryptophan

5-Hydroxytryptophan

CAS No.
56-69-9
Chemical Name:
5-Hydroxytryptophan
Synonyms
HYDROXYTRYPTOPHAN;5-HYDROXY-DL-TRYPTOPHAN;2-AMINO-3-(5-HYDROXY-1H-INDOL-3-YL)PROPANOIC ACID;DL-5-HTP;DL-5-HYDROXYTRYPTOPHAN;NSC-92523;USAF CB-96;nci-c56644;JACS-56-69-9;5-HTP AMino acid
CBNumber:
CB0110022
Molecular Formula:
C11H12N2O3
Molecular Weight:
220.22
MDL Number:
MFCD00005651
MOL File:
56-69-9.mol
Last updated:2024-12-18 13:37:16

5-Hydroxytryptophan 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
solubility DMSO (Slightly), Methanol (Slightly)
form solid
pka 2.22±0.10(Predicted)
color Off-White to Pale Beige
Water Solubility Soluble in water (4 mg/ml at 25°C), methanol.
Merck 14,4847
BRN 88199
InChIKey LDCYZAJDBXYCGN-UHFFFAOYSA-N
LogP -0.292 (est)
CAS DataBase Reference 56-69-9(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 9181P3OI6N
EPA Substance Registry System Tryptophan, 5-hydroxy- (56-69-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H332-H302
Precautionary statements  P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312
Safety Statements  26
WGK Germany  3
RTECS  YN7100000
PackingGroup  III
Hazardous Substances Data 56-69-9(Hazardous Substances Data)
NFPA 704
1
0 0

5-Hydroxytryptophan price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 797103 5-Hydroxy-DL-tryptophan 56-69-9 5mg $75.6 2024-03-01 Buy
Alfa Aesar A12237 DL-5-Hydroxytryptophan, 99% 56-69-9 1g $54.2 2021-12-16 Buy
Alfa Aesar A12237 DL-5-Hydroxytryptophan, 99% 56-69-9 5g $227 2021-12-16 Buy
Usbiological 278692 DL-5-Hydroxytryptophan 56-69-9 50g $342 2021-12-16 Buy
TRC H975700 5-HydroxyTryptophan 56-69-9 5g $140 2021-12-16 Buy
Product number Packaging Price Buy
797103 5mg $75.6 Buy
A12237 1g $54.2 Buy
A12237 5g $227 Buy
278692 50g $342 Buy
H975700 5g $140 Buy

5-Hydroxytryptophan Chemical Properties,Uses,Production

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, slightly salty in taste, soluble in methanol, ethanol, DMSO and other organic solvents, derived from African Ghana seeds.

Originator

Levotonine,Panmedica,France,1973

Uses

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

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.

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.

Definition

ChEBI: 5-hydroxytryptophan is a tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5. It has a role as a human metabolite and a neurotransmitter.

Preparation

The synthesis of 5-hydroxytryptophan (5-HTP) by the condensation of 5-benzyloxygramine with diethyl formaminomalonate, followed by saponification, decarboxylation, and hydrogenolysis was described in 1951 and 1954 and was an application of gramine synthesis, developed by Snyder and Smith ten years before. A few years later, another application of gramine synthesis was reported. In the same year, Frangatos and Chubb reported an application of the convenient tryptophan synthesis developed ten years before by eliminating the difficult and tedious preparation of 5-benzyloxyindole. The p-benzyloxyphenylhydrazone of γ,γ-dicarbethoxy-γ-acetamido-butyraldehyde (I) was prepared and cyclized, without isolation, to form ethyl β-(5-benzyloxyindol-3-)-αcarbethoxy-α-acetamidopropioilate (II). Saponification and partial decarboxylation of II, followed by hydrolysis of the acetamido group, gave 5-benzyloxytryptophan (III). 5-HTP was obtained by hydrogenolysis of III (Figure 1). However, this synthetic method suffers from the difficulty involved in the regioselective hydroxylation of tryptophan.
synthesis of 5-hydroxytryptophan
synthesis of 5-hydroxytryptophan (5-HTP)

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

Biosynthesis

5-Hydroxytryptophan, an intermediate molecule in the serotonin biosynthesis pathway, is formed by the addition of a hydroxyl (OH) group to the fifth carbon of the indole ring of tryptophan. It is used as an antiepileptic and antidepressant.

Biochem/physiol Actions

Immediate precursor of serotonin; L-aromatic amino acid decarboxylase substrate.

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.

619-60-3
126216-42-0
54737-34-7
56-69-9
Synthesis of 5-Hydroxytryptophan from 4-(dimethylamino)phenol and Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-
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View Lastest Price from 5-Hydroxytryptophan manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
5-Hydroxytryptophan pictures 2024-12-22 5-Hydroxytryptophan
56-69-9
 US $100.00-75.00 / kg 1kg 99% 5000 HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
5-Hydroxytryptophan pictures 2024-12-20 5-Hydroxytryptophan
56-69-9
 US $150.00 / kg 1kg 99% 500kg Hebei Zhuanglai Chemical Trading Co Ltd
5-Hydroxytryptophan pictures 2024-12-20 5-Hydroxytryptophan
56-69-9
 US $0.00 / KG 1KG ≥98% HPLC 1000KG Changsha Staherb Natural Ingredients Co., Ltd.
  • 5-Hydroxytryptophan pictures
  • 5-Hydroxytryptophan
    56-69-9
  • US $0.00 / KG
  • ≥98% HPLC
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5-Hydroxytryptophan Spectrum

DL-2-AMINO-3-(5-HYDROXYINDOLYL)PROPIONIC ACID 5-Hydroxytryptophan(5-HTP) DL-2-Amino-3-(5-hydroxyindolyl)propionic acid, DL-5-HTP 5-HTP (Griffonia Seeds P.E.) 5-Hydroxy-α-amino-1H-indole-3-propionic acid NSC-92523 USAF CB-96 2-azanyl-3-(5-hydroxy-1H-indol-3-yl)propanoic acid 5-HTP AMino acid 5-Hydroxytryptophan (CAS 56-69-9) 5-Hydroxy-DL-tryphophane Tryptophan, 5-hydroxy- 5-Hydroxytryptophan (5-HTP) Synonyms DL-5-Hydroxytryptophan 5-Hydroxytryptophan DL-5-Hydroxytryptophan 5-HYDROXYTRYPTOPHAN 2-AMINO-3-(5-HYDROXY-1H-INDOL-3-YL)-PROPIONIC ACID 5-hydroxy-tryptopha 5-hydroxytryptophane 5-hydroxytrytophan nci-c56644 TIMTEC-BB SBB003354 5-HydroxyTryptophane (5-HTP) 5-Hydroxy-L-Tryptophan 5-Hydroxy-Tryptophan DL-5-HYDROXYTRYPTOPHAN 99% DL-5-HYDROXYTRYPTOPHAN, 99+% BY HPLC REFERENCE STANDARD 5-Hydroxytryptophan20%50%90%99% 5-Hydroxy-DL-tryptophane H-DL-Trp(5-OH)-OH 5-Hydroxytryptophan USP/EP/BP (114-03-4) 5-hydroxytryptophan 5-Hydroxytryptophan 56-69-9 JACS-56-69-9 5-Hydroxy-DL-tryptophan> DL-5-HTP DL-5-HYDROXYTRYPTOPHAN HYDROXYTRYPTOPHAN 5-HYDROXY-DL-TRYPTOPHAN 2-AMINO-3-(5-HYDROXY-1H-INDOL-3-YL)PROPANOIC ACID Griffonia Seed Extract / 5-Hydroxytryptophan / 5-Htp Griffonia seed extract 5-HTP Powder 5-Hydroxytryptophan Tryptophan Impurity 64 L/D-5-Hydroxytryptophan 56-69-9 Indoles Tryptophans Inhibitors Plant extracts Herb extract chemical reagent pharmaceutical intermediate phytochemical reference standards from Chinese medicinal herbs (TCM). standardized herbal extract Amines Heterocycles Intermediates & Fine Chemicals Metabolites & Impurities Pharmaceuticals