ChemicalBook > CAS DataBase List > 5-Hydroxytryptophan

5-Hydroxytryptophan

Product Name
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
Formula Weight
220.22
MOL File
56-69-9.mol
More
Less

5-Hydroxytryptophan Property

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
CAS DataBase Reference
56-69-9(CAS DataBase Reference)
EPA Substance Registry System
Tryptophan, 5-hydroxy- (56-69-9)
More
Less

Safety

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

Hazard and Precautionary Statements (GHS)

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
797103
Product name
5-Hydroxy-DL-tryptophan
Packaging
5mg
Price
$121
Updated
2023/01/07
Alfa Aesar
Product number
A12237
Product name
DL-5-Hydroxytryptophan, 99%
Packaging
1g
Price
$54.2
Updated
2021/12/16
Alfa Aesar
Product number
A12237
Product name
DL-5-Hydroxytryptophan, 99%
Packaging
5g
Price
$227
Updated
2021/12/16
TRC
Product number
H975700
Product name
5-HydroxyTryptophan
Packaging
5g
Price
$140
Updated
2021/12/16
TRC
Product number
H975700
Product name
5-HydroxyTryptophan
Packaging
50mg
Price
$65
Updated
2021/12/16
More
Less

5-Hydroxytryptophan Chemical Properties,Usage,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.

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 (5-HTP)

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.

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

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.

5-Hydroxytryptophan Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

View Lastest Price from 5-Hydroxytryptophan manufacturers

Wuhan Senwayer Century Chemical Co.,Ltd
Product
5-hydroxytryptophan ;5-htp 56-69-9
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20 tons
Release date
2022-10-31
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
5-Hydroxytryptophan 56-69-9
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2021-03-01
Hebei Guanlang Biotechnology Co., Ltd.
Product
5-Hydroxytryptophan 56-69-9
Price
US $1.00/PCS
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2021-03-30

56-69-9, 5-HydroxytryptophanRelated Search:


  • 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.)
  • 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)PROPANOIC ACID
  • 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
  • (114-03-4) 5-hydroxytryptophan
  • 5-Hydroxytryptophan 56-69-9
  • JACS-56-69-9
  • 5-Hydroxy-DL-tryptophan&gt
  • 5-Hydroxytryptophan USP/EP/BP
  • Griffonia Seed Extract / 5-Hydroxytryptophan / 5-Htp
  • Griffonia seed extract 5-HTP Powder 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
  • Standard extract