L-Tryptophan

For Research Use Only.
Category
Alkaloids
Cat.No.
NP0603
CAS
73-22-3
Product Name
L-Tryptophan
Structure

Product Details

Description
L-Tryptophan is an essential amino acid and a precursor to both serotonin and melatonin. Serotonin is a neurotransmitter playing a role in regulating appetite, sleep, mood, and pain. Melatonin is a hormone modulating sleep and wakefulness.
Protein supplement in health care products.
Synonyms
H-Trp-OH; L-Tryptophane; L-Tryptohan; Tryptophan, L-; (-)-Tryptophan; (2S)-2-Azaniumyl-3-(1H-indol-3-yl)propanoate; (S)-2-Amino-3-(1H-indol-3-yl)propanoic acid; (S)-Tryptophan; (S)-α-Amino-1H-indole-3-propanoic acid; (S)-α-Amino-β-indolepropionic acid; (S)-α-Aminoindole-3-propionic acid; 1H-Indole-3-alanine, (S)-; 1H-Indole-3-propanoic acid, α-amino-, (S)-; 2-Amino-3-indolylpropanoic acid; 3-Indol-3-ylalanine; L-(-)-Tryptophan; L-Alanine, 3-(1H-indol-3-yl)-; EH 121; l-α-Aminoindole-3-propionic acid; l-β-3-Indolylalanine; Lyphan; NSC 13119; Tryptophan; Tryptophane
IUPAC Name
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Molecular Weight
204.23
Molecular Formula
C11H12N2O2
Canonical SMILES
C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N
InChI
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
InChIKey
QIVBCDIJIAJPQS-VIFPVBQESA-N
Boiling Point
447.9±35.0°C at 760 mmHg
Melting Point
282°C
Purity
>98%
Density
1.362±0.06 g/cm3
Solubility
Soluble in Water
Appearance
White to Slightly Yellowish Crystals or Crystalline Powder
Application

L-Tryptophan is an essential amino acid that plays a vital role in a variety of physiological and biochemical processes in the human body. Since the human body cannot synthesize L-Tryptophan, it must be obtained from food sources such as meat, dairy products, nuts, seeds, and legumes. The fundamental importance of L-Tryptophan lies in its involvement in the synthesis of key molecules such as serotonin, melatonin, and niacin, making it key to numerous therapeutic and nutritional interventions. The many applications of L-Tryptophan in health and medicine:

Function in Serotonin Synthesis: One of L-tryptophan's primary uses is in the synthesis of serotonin. One neurotransmitter that significantly affects mood, emotion, and sleep is serotonin. Following consumption of food, L-tryptophan is carried to the brain, where it is changed into 5-hydroxytryptophan (5-HTP) and then serotonin. Sufficient quantities of serotonin are necessary for stable moods and good general health.

Treatment of Mood and Depression: One of L-tryptophan's primary uses is the management of mood disorders, especially depression. L-tryptophan is necessary to keep serotonin levels in the brain at optimal levels since it is a precursor to serotonin. Serotonin's function in controlling mood and emotion has earned it the moniker ""feel-good"" neurotransmitter. Studies reveal that symptoms of anxiety and depression are more common in those with low serotonin levels. L-tryptophan supplements may help patients raise their brain's serotonin levels, which can lessen depression symptoms and encourage happier feelings.

Treatment for Sleep Disorders: L-tryptophan is recognized for its possible advantages in fostering sound sleep habits in addition to its function in mood regulation. The brain uses L-tryptophan to produce serotonin, which can subsequently be further processed to produce melatonin, a hormone that controls sleep-wake cycles. Melatonin's role in promoting relaxation and inducing sleep has earned it the moniker ""sleep hormone."" Increasing the body's supply of L-tryptophan may lead to better sleep patterns and higher-quality sleep for individuals.

Synthesis of Niacin: Another significant chemical made from L-tryptophan is niacin, also known as vitamin B3. The synthesis of energy and cellular metabolism depend on niacin. Although the body is capable of converting L-tryptophan to niacin, this process is not particularly effective; roughly 60 mg of L-tryptophan are needed to generate 1 mg of niacin. But in cases where dietary niacin consumption is inadequate, L-tryptophan can be taken as a supplement to assist avoid pellagra and other disorders like niacin deficient.

Pain Management: Emerging research also suggests the potential of L-tryptophan in pain management. The role of serotonin in regulating pain perception is well established. By enhancing serotonin synthesis, L-tryptophan can help reduce pain perception. Some studies suggest that supplementing with L-tryptophan may benefit conditions such as chronic pain syndromes, fibromyalgia, and migraines.

Immune Function: L-tryptophan is also involved in maintaining a strong immune system. It is a precursor to kynurenine, which plays a role in immune tolerance and regulation. Immune cells metabolize L-tryptophan to regulate T-cell function and defend against pathogens. Therefore, ensuring adequate intake of L-tryptophan can support the immune system and make the body more resistant to infection and disease.

Dietary Supplements and Applications: In dietary supplements, L-tryptophan is available in a variety of forms, including tablets, capsules, and powders. These supplements are often used to treat depression, anxiety, insomnia, and premenstrual dysphoric disorder (PMDD). In clinical settings, L-tryptophan is often used to improve mood, improve sleep quality, and support cognitive and immune function.

Storage
Store at RT
EINECS
200-795-6
Form
Powder
MDL
MFCD00064340
pH
A 1% solution in water has a pH of 5.5 to 7.;
Vapor Pressure
2.1X10-9 mm Hg at 25 deg C (est);
WGK Germany
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