56-69-9 Usage
Uses
Used in Pharmaceutical Industry:
5-Hydroxytryptophan is used as an intermediate in the natural synthesis of tryptophan to serotonin for supporting healthy serotonin levels in the body. The conversion of 5-HTP to serotonin involves the enzymatic removal of a carboxyl group (COOH), which is essential for the regulation of endocrine and brain activity.
Used in Dietary Supplements:
5-Hydroxytryptophan is used as a dietary supplement made from the seeds of the African plant Griffonia simplicifolia. It has been utilized in alternative medicine as a possibly effective aid in treating depression or fibromyalgia.
Used in Herbal Supplements:
5-Hydroxytryptophan is often sold as an herbal supplement for various purposes, including insomnia, alcohol withdrawal, headaches, premenstrual syndrome, binge-eating related to obesity, attention deficit disorder, and muscle spasms in the mouth. However, it is essential to purchase herbal/health supplements from a reliable source to minimize the risk of contamination, as there are no regulated manufacturing standards in place for many herbal compounds.
Used in Research and Clinical Studies:
5-Hydroxytryptophan is used as a human metabolite and a neurotransmitter in research and clinical studies to understand its role in various physiological processes and its potential therapeutic applications.
Used in Chemical and Pharmaceutical Manufacturing:
5-Hydroxytryptophan, being an off-white to pale beige solid with slightly salty taste and solubility in methanol, ethanol, DMSO, and other organic solvents, is used as a starting material or intermediate in the synthesis of various pharmaceutical compounds and products.
Originator
Levotonine,Panmedica,France,1973
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)
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.
Check Digit Verification of cas no
The CAS Registry Mumber 56-69-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 6 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 56-69:
(4*5)+(3*6)+(2*6)+(1*9)=59
59 % 10 = 9
So 56-69-9 is a valid CAS Registry Number.
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-/m0/s1
56-69-9Relevant academic research and scientific papers
Syntheses of Substituted L- and D-Tryptophans
Irie, Kunihiko,Ishida, Akihiko,Nakamura, Tohru,Oh-ishi, Tokuro
, p. 2126 - 2139 (2007/10/02)
Several 5-substituted nb-methoxycarbonyl-L- and -D-tryptophan derivatives were synthesized from proline by a new route involving electrochemical oxidation, as well as by the known procedures.Removal of the Nb-methoxycarbonyl group was accomplished by treatment with Me3SiI in refluxing chloroform, then alkaline hydrolysis of the methyl esters afforded 5-substituted L- and D-tryptophans with high optical purities.Keywords - L-tryptophan 5-substituted; D-tryptophan 5-substituted; anodic oxidation; N-methoxycarbonyl group deprotection; Fischer indole synthesis; iodotrimethylsilane
5-HYDROXYTRYPTOPHAN AND SOLUBLE PIGMENT FORMATION IN CLAVICEPS SP. PRL 1980
Cho, Sung-Hwan,Anderson, John A.
, p. 1975 - 1976 (2007/10/02)
5-Hydroxytryptophan (156 mg/l) was identified in 15-day-old cultures of Claviceps sp.PRL 1980. DL-Tryptophan and 5-hydroxytryptophan were incorporated into the brown pigment in cultures of the same fungus, 6percent and 24percent, respectively.Key Word Index - Claviceps sp.PRL 1980; Clavicipitaceae; ergot; 5-hydroxytryptophan; pigment; biosynthesis.
One-Electron Redox Potentials of Phenols. Hydroxy- and Aminophenols and Related Compounds of Biological Interest
Steenken, S.,Neta, P.
, p. 3661 - 3667 (2007/10/02)
The rate constants for reversible electron transfer between a series of substituted phenolate ions and anilines and various substituted phenoxyl or anilino radicals in aqueous solution were measured by observing the formation or depletion of the radicals involved.Nonequilibrium concentrations of the radicals were produced in the presence of the corresponding phenols or anilines by using the pulse radiolysis technique.The relaxation of the system to equilibrium was monitored by optical detection methods.From the equilibrium constants for one-electron transfer, the one-electron redox potentials (E2) for 38 phenolic or anilino type compounds were determined, many of which are natural products.The redox potentials are strongly influenced by electron-donating or -withdrawing substituents at the aromatic system.
α-Alkyl(or aryl)thio-5-hydroxytryptophan derivative and the preparation process thereof
-
, (2008/06/13)
As a novel compound, an α-alkyl(or aryl)thio-5-hydroxytryptophan derivative and the preparation process thereof are disclosed. Said novel compound is readily convertible to 5-hydroxytryptophan having a versatile utilization.
