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L-Tryptophan

Catalog Number
ACM73223-4
CAS
73-22-3
Structure
IUPAC Name
(2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid
Synonyms
L-Beta-3-indolylalanine
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
InChI Key
QIVBCDIJIAJPQS-VIFPVBQESA-N
Boiling Point
342.72 °C
Melting Point
289-290 °C(lit.)
Purity
99%
Density
1.34 g/cm³
Solubility
Slightly soluble in acetic acid, ethanol, insoluble in ethyl ether
Appearance
White to yellow-white powder
Application
Amino acids-type drug:

It can be used in amino acid infusion, being often combined with iron and vitamins. Its co-administration with VB6 can improve depression and prevention/treatment of skin disease; as a sleep sedative, it can be combined with L-dopa for the treatment of Parkinson's disease. It is carcinogenic to experimental animals; it may cause adverse reactions including nausea, anorexia and asthmas. Avoid combination with monoamine oxidase inhibitors.

Nutritional supplements:

Tryptophan contained in egg white protein, fish meat, corn meal and other amino acids are limited; content in cereals such as rice is also low. It can be combined with lysine, methionine and threonine for enhanced amino acids. It can be supplemented to corn product at the content of 0.02% tryptophan and 0.1% lysine, being capable of significantly improving the protein potency.tryptophan is one of the 21 amino acids comprising a protein. Tryptophan is a component of the skin's natural moisturizing factors.
Storage
2-8 °C
Active Content
95%
pH
5.5-7.0 (10g/l, H₂O, 20°C)
Physical State
Solid
Typical Applications
Use as dispersing agent, emulsion stabilizer.
Spec Sheet
Case Study

L-Tryptophan Used for the Functionalization of Graphitic Carbon Nitride in Nanozyme and Fluorescence Sensing Applications

L-Tryptophan Used for the Functionalization of Graphitic Carbon Nitride in Nanozyme and Fluorescence Sensing Applications Li, Shaohui, et al. Applied Surface Science 681 (2025): 161620.

L-Tryptophan, an essential aromatic amino acid, has recently gained attention as a versatile functionalization agent in nanomaterials engineering. Its unique structure, containing both -NH₂ and -COOH groups, provides abundant reactive sites for surface modification, while its indole moiety enables π-π stacking interactions with conjugated systems. In a recent study, L-tryptophan was employed to functionalize graphitic carbon nitride (g-C₃N₄), generating L-g-C₃N₄ with significantly enhanced dispersibility in aqueous media compared to bulk g-C₃N₄.
The functionalization was achieved through ultrasonic-assisted assembly, where L-tryptophan established strong π-π interactions with g-C₃N₄ sheets. This modification not only improved solubility but also introduced additional carboxyl groups, facilitating uniform deposition of cerium oxide (CeO₂) nanoparticles in subsequent hydrothermal synthesis. The resulting CeO₂/L-g-C₃N₄ nanocomposite exhibited remarkable oxidase-like catalytic activity, effectively catalyzing the oxidation of 3,3',5,5'-tetramethylbenzidine (TMB) into its colored product.
Beyond catalytic enhancement, the L-tryptophan functionalization also enabled advanced sensing applications. Coupling the nanocomposite's fluorescence properties with redox-mediated quenching, a novel on-off-on sensing platform was established for the selective detection of Cr(VI) and SO₃²⁻ ions. Theoretical analysis confirmed that the improved activity stemmed from reduced binding energy of intermediates on the modified surface.
This case study highlights the critical role of L-tryptophan in tuning the physicochemical properties of g-C₃N₄, enabling multifunctional nanocomposites with potential applications in biosensing, environmental monitoring, and nanozyme-based catalysis.

L-Tryptophan as a Kinetic Promoter for Carbon Dioxide Hydrate Formation in CCS Applications

L-Tryptophan as a Kinetic Promoter for Carbon Dioxide Hydrate Formation in CCS Applications Khandelwal, Himanshu, et al. Energy & Fuels 35.1 (2020): 649-658.

L-Tryptophan, an essential amino acid widely recognized for its biological importance, has recently emerged as a promising additive in gas hydrate-based carbon capture and storage (CCS) technologies. One of the critical challenges in CO₂ hydrate formation is the inherently slow kinetics, which limit the feasibility of large-scale applications. In this context, L-tryptophan was evaluated as an environmentally friendly kinetic promoter in hydrate synthesis experiments conducted within a stirred tank reactor.
Systematic studies revealed that the addition of L-tryptophan significantly improved hydrate formation rates. At an optimal concentration of 300 ppm, the process achieved an average gas uptake of 114 v/v, corresponding to 78% water-to-hydrate conversion at 273.65 K and 3.4 MPa. This represented a four-fold increase compared to the control system without promoter. Notably, higher concentrations (1000 ppm) did not further enhance performance, suggesting a saturation effect.
Temperature played a crucial role in modulating hydrate kinetics. Lower operating temperatures (273.65-275.65 K) yielded shorter induction times and greater gas uptake relative to experiments at 277.65 K. The enhanced performance is attributed to L-tryptophan's ability to facilitate nucleation and stabilize hydrate growth, likely through hydrogen-bonding interactions and hydrophobic effects.
With its low effective dosage, high efficiency, and environmental compatibility, L-tryptophan offers a practical pathway for advancing hydrate-based CCS technologies. Its integration into industrial-scale processes may provide a sustainable and efficient solution to reduce CO₂ emissions, contributing to global climate mitigation strategies.

L-Tryptophan as a Green Kinetic Promoter for Methane Hydrate Formation

L-Tryptophan as a Green Kinetic Promoter for Methane Hydrate Formation Shen, X., Li, Y., Li, Y., Shen, L., Maeda, N., Zhang, Y., ... & Wang, X. (2023). ACS Sustainable Chemistry & Engineering, 11(24), 8774-8785.

L-Tryptophan, an environmentally friendly amino acid, has recently been evaluated as a promising additive in hydrate-based gas solidification technology. Methane hydrates, though attractive for energy storage and gas transport, face kinetic limitations that hinder large-scale application. Traditional surfactant promoters such as sodium dodecyl sulfate (SDS) improve nucleation, but their environmental impact raises concerns. L-Tryptophan provides a sustainable alternative with unique advantages in hydrate growth kinetics.
Experimental investigations conducted under isothermal and isochoric conditions revealed that L-tryptophan did not significantly accelerate nucleation rates but exhibited superior promotion of hydrate growth compared to SDS. Remarkably, effective promotion was achieved at concentrations as low as 0.1 wt %, with negligible performance gains beyond this threshold. At 0.1 wt %, the ultimate methane gas consumption increased by 46.52% and the time to reach 90% gas uptake (t90) decreased by 33.67% when pressure was raised from 7 to 11 MPa. Temperature variations (273.65-277.15 K) influenced both gas consumption and hydrate growth time, highlighting the importance of thermodynamic conditions.
Macroscopic morphology observations demonstrated that hydrates nucleated preferentially at the gas-liquid-solid interface, spreading as thin films before expanding and climbing container walls. At higher L-tryptophan concentrations (>0.5 wt %), hydrates developed as loose, porous structures with capillary-driven solution transport.
This study underscores the potential of L-tryptophan as a sustainable kinetic promoter, offering efficient hydrate growth with minimal dosage, advancing the feasibility of hydrate-based methane storage and transport technologies.

Custom Q&A

What is the molecular formula of L-Tryptophan according to the reference?

The molecular formula of L-Tryptophan is C11H12N2O2.

What is the molecular weight of L-Tryptophan according to the reference?

The molecular weight of L-Tryptophan is 204.22 g/mol.

What are some synonyms for L-Tryptophan mentioned in the reference?

Some synonyms for L-Tryptophan are tryptophan, L-Tryptophane, and h-Trp-oh.

What role does L-Tryptophan have according to the reference?

L-Tryptophan has a role as an antidepressant, a nutraceutical, a plant metabolite, and a human metabolite.

What is the IUPAC name of L-Tryptophan?

The IUPAC name of L-Tryptophan is (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid.

What is the InChIKey of L-Tryptophan?

The InChIKey of L-Tryptophan is QIVBCDIJIAJPQS-VIFPVBQESA-N.

What is the Canonical SMILES of L-Tryptophan?

The Canonical SMILES of L-Tryptophan is C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N.

What is the EC Number of L-Tryptophan?

The European Community (EC) Number of L-Tryptophan is 200-795-6.

What is the UNII number of L-Tryptophan?

The UNII number of L-Tryptophan is 8DUH1N11BX.

What is the ChEMBL ID of L-Tryptophan?

The ChEMBL ID of L-Tryptophan is CHEMBL54976.

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