34271-54-0

Basic information

• Product Name: L-Theanine
• Synonyms: DL-THEANINE;H-DL-The-OH;2-Amino-4-(ethylcarbamoyl)butanoic acid;N-Ethyl-L-glutamine;2-amino-5-(ethylamino)-5-oxopentanoic acid;REF DUPL: DL-Theanine;DL-Theanine DL-Theanine;DL-Theanine (NgaMMa-ethyl-L-glutaMine)
• CAS NO: 34271-54-0
• Molecular Formula: C₇H₁₄N₂O₃
• Molecular Weight: 174.2
• Product Categories: Amino Acids
• Mol File: 34271-54-0.mol
• Article Data: 26

Chemical Properties

• Melting Point: 200 °C
• Boiling Point: 430.2 °C at 760 mmHg
• Flash Point: 214 °C
• Appearance: /
• Density: 1.171 g/cm³
• Vapor Pressure: 1.32E-08mmHg at 25°C
• Refractive Index: 1.492
• Storage Temp.: 2-8°C
• Solubility: Water (Sparingly)
• PKA: 2.24±0.10(Predicted)
• CAS DataBase Reference: L-Theanine(CAS DataBase Reference)
• NIST Chemistry Reference: L-Theanine(34271-54-0)
• EPA Substance Registry System: L-Theanine(34271-54-0)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 28-36/37
• Hazardous Substances Data: 34271-54-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H14N2O3/c1-2-9-6(10)4-3-5(8)7(11)12/h5H,2-4,8H2,1H3,(H,9,10)(H,11,12)

Upstream product

• 95082-77-2 Z-L-theanine 
• 73270-47-0 L-glutamic acid-5-ethyl ester; hydrochloride 
• 75-04-7 ethylamine 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 557-66-4 ethanamine hydrochloride 
• 142-47-2 monosodium glutamate 
• 56-85-9 L-glutamine 
• 149834-97-9 (S)-4-Ethylcarbamoyl-2-(trityl-amino)-butyric acid 
• 70-18-8 GLUTATHIONE 
• 865758-94-7 (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-ethylcarbamoyl-butyric acid 
• 142-47-2 monosodium L-glutamate 
• 340-90-9 N-phthaloyl-L-glutamic acid 
• 25830-77-7 N-phthaloyl-L-glutamic anhydride 
• 1676-73-9 L-glutamic acid γ-benzyl ester 

Downstream Products

• 77935-58-1 Boc-theanine (Boc-Tea-OH) 
• 77935-68-3 theanyl-L-alanine (H-Tea-L-Ala-OH) 
• 77935-69-4 H-Tea-L-Ala-L-Ala-OH 
• 77935-63-8 Boc-Tea-L-Ala-OH 
• 77935-70-7 theanyl-L-alanyl-L-alanyl-L-alanine (H-Tea-L-Ala-L-Ala-L-Ala-OH) 
• 77935-64-9 Boc-Tea-L-Ala-L-Ala-OH 
• 77935-59-2 Boc-Tea-ONp 
• 77935-60-5 Boc-Tea-L-Ala-OBzl 
• 77935-65-0 Boc-Tea-L-Ala-L-Ala-L-Ala-OH 
• 77935-61-6 Boc-Tea-L-Ala-L-Ala-OBzl 
• 77935-66-1 H-Tea-L-Ala-OBzl_.HCl 
• 766460-08-6 Boc-Tea-L-Ala-L-Ala-L-Ala-OBzl 
• 77935-67-2 H-Tea-L-Ala-L-Ala-L-Ala-OBzl_.HCl 
• 910541-97-8 L-theanyl-L-theanine 

Relevant articles and documents

Varietal Differences in the Total and Enantiomeric Composition of Theanine in Tea

Theanine is the main amino acid component in tea. It usually constitutes between 1 and 2% of the dry weight of the tea leaves. It is as prevalent in tea as all other free amino acids combined. Both enantiomers of theanine were found to have a similar sweet taste, with little or no aftertaste. It was found that black and half-green teas (except for Formosa Oolong) contained as much, or more, theanine as green teas. No correlation was found between the absolute concentration of theanine in tea and its enantiomeric composition. An inverse correlation was found between certain grades of tea (e.g., pekoe, Flowery Orange Pekoe, etc.) and the percent of D-theanine present. This could provide the basis for a reproducible, scientific method to grade and/or evaluate teas. Theanine slowly racemizes in aqueous solution. It also undergoes hydrolysis, particularly at basic pH values. By monitoring these processes, information may be gleaned on the production, storage, handling, and shipping of tea and tea products.

Preparation method of L-theanine

The invention relates to the technical field of organic chemical synthesis, in particular to a preparation method of L-theanine. The preparation method of the L-theanine comprises the following steps:(a) reacting L-glutamic acid with a copper salt in a solvent to obtain a chelate A; (b) carrying out an esterification reaction on the chelate A and methanol to obtain a compound B; and (c) after a reaction of the compound B with an aqueous ethylamine solution is finished, adding a decoppering reagent, carrying out stirring for a reaction, and removing a solvent to obtain a crude L-theanine product. According to the preparation method of the L-theanine, the L-glutamic acid is used as an initial raw material and is easy to obtain; in addition, residues in amino acid are protected by adopting acopper chelate manner, so the reaction process is green and environment-friendly. In the step (c), the safer aqueous ethylamine solution is used for the reaction, so the safety of the reaction is improved, requirements on equipment are reduced, production cost is greatly saved, and industrial production is easier.

Studies on the Biochemical Formation Pathway of the Amino Acid l -Theanine in Tea (Camellia sinensis) and Other Plants

Tea (Camellia sinensis) is the most widely consumed beverage aside from water. The flavor of tea is conferred by certain metabolites, especially l-theanine, in C. sinensis. To determine why more l-theanine accumulates in C. sinensis than in other plants, we compare l-theanine contents between C. sinensis and other plant species (Camellia nitidissima, Camellia japonica, Zea mays, Arabidopsis thaliana, and Solanum lycopersicum) and use a stable isotope labeling approach to elucidate its biosynthetic route. We quantify relevant intermediates and metabolites by mass spectrometry. l-Glutamic acid, a precursor of l-theanine, is present in most plants, while ethylamine, another precursor of l-theanine, specifically accumulates in Camellia species, especially C. sinensis. Most plants contain the enzyme/gene catalyzing the conversion of ethylamine and l-glutamic acid to l-theanine. After supplementation with [2H5]ethylamine, all the plants produce [2H5]l-theanine, which suggests that ethylamine availability is the reason for the difference in l-theanine accumulation between C. sinensis and other plants.

Synthesis of amino acid using a flow-type microreactor containing enzyme-mesoporous silica microsphere composites

A flow-type microreactor containing composite materials of a theanine synthetase (glutaminase) and mesoporous silica with 23.6 nm pore diameter (SBA-15 microsphere) was developed for the continuous synthesis of l-theanine, a unique amino acid. Enzyme-immobilisation ability and enzymatic activity in the SBA-15 microsphere with large mesopores were higher than those of SBA-15 with a 5.4 nm pore diameter. Moreover, the glutaminase-SBA-15 microsphere composites displayed higher selectivity in theanine production than the free enzyme did in a batch experiment. A direct visualization of composites of fluorescently labelled glutaminase and SBA-15 microsphere immobilised in the flow channel of the microreactor by a combination of differential interference contrast and fluorescence microscopy revealed that the enzymes were uniformly dispersed throughout the mesoporous silica particles, because of the successful encapsulation of the enzyme. The enzyme-encapsulated microreactor exhibited a high conversion of l-glutamine to l-theanine with local control of the reaction temperature. In addition to this advantage of the microreaction system, the microreactor enabled the on-off regulation of enzymatic activity during continuous theanine synthesis by controlling the reaction temperature or the pH of the substrate solution.