L-Theanine

Base Information

• Chemical Name: L-Theanine
• CAS No.: 3081-61-6
• Molecular Formula: C₇H₁₄N₂O₃
• Molecular Weight: 174.2
• Hs Code.: 29241990
• UNII: 8021PR16QO
• DSSTox Substance ID: DTXSID80184817
• Nikkaji Number: J3.047C
• Wikipedia: Theanine
• Wikidata: Q909931
• NCI Thesaurus Code: C87348
• RXCUI: 38022
• Metabolomics Workbench ID: 50896
• ChEMBL ID: CHEMBL3039113
• Mol file: 3081-61-6.mol

Synonyms:delta-glutamylethylamide;gamma-glutamylethylamide;L-glutamic acid-gamma-ethylamide;theanine;theanine, (D)-isomer;theanine, (DL)-isomer;theanine, (L)-isomer

Chemical Property of L-Theanine

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 1.32E-08mmHg at 25°C
• Melting Point: 207 °C
• Refractive Index: 8 ° (C=5, H2O)
• Boiling Point: 430.2 °C at 760 mmHg
• PKA: 2.24±0.10(Predicted)
• Flash Point: 214 °C
• PSA: 92.42000
• Density: 1.171 g/cm³
• LogP: 0.40580
• Storage Temp.: Store at?0-5°C
• Solubility.: Soluble in Water (up to 20 mg/ml).
• Water Solubility.: almost transparency
• XLogP3: -3.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 174.10044231
• Heavy Atom Count: 12
• Complexity: 170

Purity/Quality:

98.0-102.0% ^*data from raw suppliers

Theanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 28-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNC(=O)CCC(C(=O)O)N
• Isomeric SMILES: CCNC(=O)CC[C@@H](C(=O)O)N
• Recent ClinicalTrials: Evaluate the Effects of a Theanine Formulation on Stress, Burnout, Mood, and Sleep in Individuals Who Report Occasional Moderate or High Levels of Stress
• Recent NIPH Clinical Trials: Effectiveness of combined use of theanine and arginine for psychological stress
• Chemical Structure and Natural Occurrence: Theanine exists in two isomers, L-form, and D-form, with only the L-form predominantly found in nature, particularly in tea plants. It shares a similar structure with glutamine and glutamate.
• Neurotransmitter Regulation: Theanine has been recognized for its regulatory role in neurodegeneration. It binds to three glutamate receptor subtypes (NMDA, AMPA, and KA), which are excitatory neurotransmitters involved in fast synaptic transmission in the central nervous system.
• Health Benefits: Theanine is associated with various health benefits, including improvements in mood, cognition, stress reduction, and anxiety relief. Supplementation of 200鈥?400 mg/day of L-theanine may assist in reducing stress and anxiety symptoms. Theanine exhibits antioxidant, anti-inflammatory, neuroprotective, anti-cancer, metabolic regulatory, cardiovascular protective, liver and kidney protective, and immune regulatory effects.
• Flavor Component in Tea: L-theanine contributes to the unique taste of tea, providing a caramel flavor and alleviating the bitterness of caffeine. It is a significant index for estimating the freshness of tea and contributes to the generation of tea volatiles, imparting desirable aromas.
• Applications and Distribution in Tea Plants: Due to its flavor and health benefits, L-theanine finds wide applications as a beverage ingredient or dietary supplement. It is distributed in different parts of tea plants, with higher contents in roots and leaves compared to stems.
• Anticancer Properties: Studies suggest that theanine possesses anticancer effects by inhibiting various pathways involved in cancer cell proliferation, apoptosis, metastasis, migration, and invasion. Further research is needed to validate its effectiveness in cancer prevention and treatment.

Technology Process of L-Theanine

There total 29 articles about L-Theanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Z-L-theanine (95082-77-2) → N-ethyl-L-glutamine (3081-61-6,5822-62-8,17010-37-6,34271-54-0)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; hydrogen; In tetrahydrofuran; at 20 ℃; for 8h;

DOI:10.1021/acschemneuro.7b00036

Reference yield: 100.0%

ethanamine hydrochloride (557-66-4) + monosodium glutamate (142-47-2) → N-ethyl-L-glutamine (3081-61-6,5822-62-8,17010-37-6,34271-54-0)

Guidance literature:

With D-glucose; 5'-adenosine monophosphate; In phosphate buffer; at 30 ℃; for 48h; pH=7;

DOI:10.1271/bbb.70663

Reference yield: 91.0%

ethylamine (75-04-7,85404-22-4) → N-ethyl-L-glutamine (3081-61-6,5822-62-8,17010-37-6,34271-54-0)

Guidance literature:

L-glutamic acid 5-methyl ester; With triethylamine; acetylacetone; In methanol; at 60 ℃; for 1h;

ethylamine; In methanol; water; for 6h; Product distribution / selectivity;

upstream raw materials:

Z-L-theanine

L-glutamic acid-5-ethyl ester; hydrochloride

ethylamine

L-glutamic acid 5-methyl ester

Downstream raw materials:

L-glutamic acid

ethylamine

Refernces

• 1、 Sebih, Fatiha,Rousset, Matthieu,Bellahouel, Salima,Rolland, Marc,De Jesus Ferreira, Marie Celeste,Guiramand, Janique,Cohen-Solal, Catherine,Barbanel, Gérard,Cens, Thierry,Abouazza, Mohammed,Tassou, Adrien,Gratuze, Maud,Meusnier, Céline,Charnet, Pierre,Vignes, Michel,Rolland, Valérie. "Characterization of l -Theanine Excitatory Actions on Hippocampal Neurons: Toward the Generation of Novel N-Methyl- d -aspartate Receptor Modulators Based on Its Backbone". . p. 1724 - 1734. Retrieved 2017/08/21.
• 2、 Chen, Xingyi,Su, Lingqia,Wu, Dan,Wu, Jing. "Application of recombinant Bacillus subtilis γ-glutamyltranspeptidase to the production of l-theanine". . p. 1429 - 1439. Retrieved 2014/11/07.